Anacortes Yacht Charters

Escape the ordinary with a San Juan Islands yacht charter vacation.

Adventure awaits

The San Juan Islands and Gulf Islands are some of the most popular cruising areas in the world.

What is it that draws people to these islands? A big reason is because the islands are remote but accessible at the same time. A short drive from Seattle or Vancouver puts you in Anacortes, Washington, the “Gateway to the San Juan Islands.” From there, the San Juan Islands start a mere 15 miles away.

Your Cruise. Your Choice.

Once in the islands, you’ll find quaint both communities and hidden hideaway, all surrounded by a calm inland sea. Seemingly endless miles of coastline and over 100 islands give you plenty of options for exploring and relaxing. Drop anchor in a quiet cove, or tie up at one of the island marinas – it’s your choice when you charter!

Anacortes Yacht Charters has provided San Juan Islands yacht charters for 45 years. We have the largest selection of motor yachts and sailboats in the Northwest. Our experience and fleet mean we can match you with the perfect boat for a trip of lifetime.

To book a bareboat or skippered San Juan Islands yacht charter contact us at:

800-233-3004 or [email protected]

Big Boat Charter Sale

We are offering our biggest savings on the biggest boats in the fleet.

Class/Charter Bundle

Save $1,900 and launch or build your bareboat charter resume.

Our Guarantee

Should you have a breakdown during your charter, we will complete repairs within four hours of notification for any vessel within 20 miles of our charter base. View Guarantee

sailboat rental san juan islands

Yacht Charter

A private yacht charter is your ticket to a Pacific Northwest vacation of a lifetime. Choose to bareboat charter a powerboat or sailboat for a hands-on adventure. Or, hire a skipper for a more guided experience. A few of our larger boats require a crew and are shown on the crewed yacht page.

sailboat rental san juan islands

Yacht Ownership

If you own a boat, or are pondering a purchase, consider placing your boat into charter service. This a great option to help offset the cost of ownership and earn real tax advantages, Use our in-house service department for year-round care of your boat. Arrange time on your boat for yourself as desired.

News and Announcements

sailboat rental san juan islands

We are proud to be celebrating our 45th Anniversary in 2024. Over the years providing San Juan Islands yacht charters, our crew has pioneered mini-fleet management. Along the way we have provided over 15,000 charter trips – illustrating our commitment to quality and customer service.

sailboat rental san juan islands

All of our charter vessels are clean, well-maintained, and include a breakdown guarantee. We take the risk out of chartering to better ensure the quality of your charter experience.

sailboat rental san juan islands

Our yacht charter fleet includes a variety of power yachts , sailing yachts and crewed yachts from 27’ to 70’.  Make your choice to host nearly any group of friends and family for a magical San Juan Islands yacht charter.

Toll Free: (800) 233-3004 | (360) 293-4555 | [email protected]

© 1979 - 2024 | All Rights Reserved, Anacortes Yacht Charters

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Sail In The San Juan Islands!

Relaxed. rejuvenated. awed by nature..

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July 7, 2024

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sailboat rental san juan islands

Sail the San Juan Islands with us!

Sit back, relax, and leave your cares behind when you sail with us for a life-changing journey on our comfortable 55' sailing yacht in the San Juan Islands. We'll show you the natural beauty of the Islands - it is our home - and we look forward to sharing it with you. Our home port is in Deer Harbor Marina, Orcas Island.

Sailing with us in the San Juans, Gulf Islands, and the Inside Passage offers a chance to see bald eagles, humpback whales, sea and shore birds, sea lions, and our resident and transient orca whales. Our multiple-day adventures include a naturalist captain and an experienced professional chef. You'll enjoy local Northwest gourmet cuisine made with fresh local ingredients. Bring us your special requests so we can make your private sailing memorable. We love customizing tours to exceed your expectations!

Our tours are a special way to experience the magic of these islands. Easy day hikes through the lush temperate rainforest of the Salish Sea, beach combing, exploring and wildlife viewing as well as sailing are the major components of our adventures - all while retreating each evening to the safe and quiet confines of our luxury sailing yacht.

We do group, private and custom charters and curate unique itineraries that include remote islands, wildlife viewing, gourmet meals, and activities. If your time is limited, you can take a day trip on one of our six-hour sailing tours from Deer Harbor Marina on Orcas Island.

sailboat rental san juan islands

3-Day All Inclusive Sailing Tour of the San Juan Islands

Join us for an all-inclusive multi day sailing tour of the most beautiful marine environment in the world!

Prices start at $1999 USD per person. Early and late season discounts available. Gratuities are welcome, but not included in cost of trip.

2024 Dates for 3-Day Tour:

Please note: THE DATES BELOW DO NOT REFLECT CURRENT RESERVATIONS. Please use the "Check Availability" button on this page to see a real-time calendar.

May: 5/10-5/12 June: 6/7-6/9 September: 9/7-9/9, 9/13-9/15, 9/18-9/20

If the dates you want are not listed above, please contact us. We are very flexible, and can often adjust the sailing schedule, and can create tours of any duration.

Our multi-day, all-inclusive sailing tours are the best way to unwind, relax and immerse yourself in the Salish Sea's natural beauty. With each day aboard, you'll feel a deeper connection to the natural world as you let the stresses of everyday land-based life melt away. We follow the rhythms of the wind and tides to show you the true beauty of this magical archipelago.

Sailing from our home port of Deer Harbor, Orcas Island, we are quickly in one of the most scenic and wildlife-rich areas of the world. Our naturalist captain will hoist the sails and guide your small group in an intimate exploration of wildlife and nature by eco-friendly sail power.

Sailing aboard the S/V Nawalak is about escaping the crowds, relaxing, and connecting with nature and the sea while exploring the quiet beaches and pristine islands of the northwest. During our tours we share with you the gems and secrets we’ve discovered in our 30+ years of sailing these amazing waterways.

sailboat rental san juan islands

Sail & Paddle Tour

New this year!

Hey there, avid kayaker or paddle boarder! Think you've seen and conquered it all? We invite you to paddle the mystical waters of the San Juan Islands, while you return each evening to the safe, warm and cozy confines of our luxury 55' sailboat.

Aboard Sailing vessel Nawalak, you'll be treated to 3 luxury meals per day by our on-board chef to fuel your kayaking journeys, as well as a warm, dry berth aboard. No need to pitch a tent, or haul heavy gear - keep it all on the boat!

This tour blends the elegant simplicity of sailing with the intimacy of near shore kayaking, utilizing our vessel as a mother ship for your San Juan Islands kayaking adventures. This is a bring-your-own-kayak adventure where we board, our luxury 55' sail boat and sail deep into the majestic waters of the San Juan Islands. By sailing to these highly sought after kayaking destinations, we eliminate the hassle, and danger of paddling across large bodies of open sea to get to our coveted kayaking destinations. Tour durations are from 3-6 days, and are fully customizable for duration, skill levels and dates. Give us a call to learn more.

sailboat rental san juan islands

5-Day All Inclusive Sailing Tour of the San Juan Islands

Join us for an all-inclusive 5-Day sailing tour of the most beautiful marine environment in the world!

All inclusive prices start at $2499 USD per person. Early and late season discounts available. Gratuities are welcome, but not included in cost of trip.

2024 Dates for 5-Day Tour:

Please note: THE DATES BELOW DO NOT REFLECT CURRENT RESERVATIONS. Please use the "Check Availability" button on this page to see a real-time calendar. If the dates you want are not listed, please contact us. We are very flexible, and can often adjust the sailing schedule, and can create tours of any duration.

May: 5/3-5/7, 5/17-5/21, 5/31-6/4, June: 6/18-6/22, July: 7/2-7/6, 7/16-7/20, August: 8/1-8/5, 8/16-8/20, 8/31-9/4,

sailboat rental san juan islands

6-Day All Inclusive Sailing Tour of the San Juan Islands

Join us for an all-inclusive 6-Day sailing tour of the most beautiful marine environment in the world!

All inclusive prices start at $2699 USD per person. Early and late season discounts available. Gratuities are welcome, but not included in cost of trip.

2024 Dates for 6-Day Tour:

May: 5/24-5/29 June: 6/11-6/16, 6/25-6/30 July: 7/9-7/14, 7/24-7/29 August: 8/8-8/13, 8/23-8/28

Our multi-day, all inclusive sailing tours are the best way to unwind, relax and immerse yourself in the Salish Sea's natural beauty. With each day aboard, you'll feel a deeper connection to the natural world as you let the stresses of everyday land based life melt away. We follow the rhythms of the wind and tides to show you the true beauty of this magical archipelago.

sailboat rental san juan islands

San Juan Islands 6-hour Day Sail

Climb aboard and immerse yourself in the vibrant beauty of the San Juan Islands.

All inclusive prices start at $229 USD per person, check dates on the right. Please note: If the dates you want are not listed, or another tour is designated, please contact us. We can often adjust the sailing schedule.

sailboat rental san juan islands

INSIDE PASSAGE - Desolation Sound, Broughton Archipelago & Great Bear Rainforest

We will be offering this tour again in late August/early September 2025. Please use the contact form on this page to let us know you have interest, or have any questions. Prices are yet to be determined, but will probably be around $5999 per person all inclusive of food and beverages.

Sail with us to where civilization gradually fades astern. Northwest is where we're headed, underneath a golden sky as we begin to get a taste of the wilder side of the North American coast. Natural Hot Springs, 10,000 yr old protected First Nation villages, ancient totem poles, pods of leaping dolphins, Orcas, Humpbacks, Bears, Rain Wolves. These are just some of the highlights on our farthest north tour. This is a true adventure, but with all the creature comforts and safety we've developed from over 20 years of experience with this route.

We pass north through the Inside Passage roughly retracing the route that Captain George Vancouver did in 1792. Much of the area looks the same now as it did then. With each day aboard, you'll feel a deeper connection to the natural world as you let the stresses of everyday land based life melt away.

Why choose us?

Experience The Magic Of Sailing In The San Juan Islands

Emerald Isle sails on a beautiful 55' sailing vessel with the latest upgrades for private charter safety and comfort. Our naturalist captain is U.S. Coast Guard licensed. You'll enjoy a sailing charter with a quiet charging system using wind and solar power, and the only heated pilothouse charter sailboat in the area.

Our tours are led by Emerald Isle Sailing's owner/operator.

Sit back and relax while our gourmet chef prepares another sumptuous meal! Our spacious, fully equipped 55’ custom pilot house sailboat will keep you warm and dry if we encounter a rain shower. After a day on the water or exploring the rainforest ashore, retire to one of 5 private staterooms with fresh linens, towels, and toiletries included. A luxury sailing package!

Feel yourself slipping into a deeper connection with nature as we sail to remote coves, harbors, and anchorages. The stresses of land-based life will quickly melt away. Read a book in the protected cockpit, or take the helm and feel the silent energy of the wind move the boat through tranquil waters.

On our 5, and 6-day tours, we venture farther to where civilization fades astern. Bigger waters, bigger wildlife, and bigger adventures await - all from the comfort and safety of our USCG-documented vessel.

San Juan Islands, Washington

The San Juan Islands include 172 named islands and reefs off the coast of Washington State. Departing from Anacortes, the Washington State Ferries serve Orcas Island, Lopez Island, and San Juan Island. Each island offers a unique opportunity for adventure. Activities include sailing, hiking, biking, kayaking, and enjoying the simple rustic beauty of the San Juan Islands.

The San Juan Islands enjoy a moderate year-round climate. Winters experience an average temperature of 40 degrees F, while summers enjoy a glorious average of 70 degrees F. Sailing with us in the San Juan Islands offers a chance to spot humpback whales, orcas, and minke whales, and see flower-filled meadows, mountain-framed horizons, hidden coves, and emerald waters. The beauty of this area casts a spell hard to undo.

Frequently asked questions

What kinds of wildlife might i see.

The coastlines we sail are rich with life. Depending on the time of year, sea mammals you might see include Orca, Humpback and Minke Whales, Harbor Porpoise, Dahl’s Porpoise, White-sided Dolphins, Sea Otters, River Otters, Harbor Seals, and Sea Lions.

On land you have the opportunity to see Minks, Otters, Black-tailed Deer, Raccoons, and imported exotic wildlife. As we journey northward it becomes increasingly likely to find coastal Wolves, Mountain Goats, Black Bears, Grizzlies, and the White Kermode, or “Spirit” Bear.

There are too many feathered friends to list. The Bald Eagle is a daily visitor. Other favorites of ours include Oyster Catchers, Marbled Murrelettes, Scoters, and Great Blue Herons. For a truly world class natural experience the old-growth forests of northern B.C.’s Great Bear Rainforest house an especially rich and diverse community of creatures. Our unobtrusive electric powered dingy allows us the unique advantage of near silence while viewing and photographing wildlife.

What sort of clothes should I bring?

It’s best to be prepared for a temperature range of 55° to 80° F. When sailing, even on a warm summer day, the breeze experienced on deck when heading up wind can elicit the need for cozier clothing. The best dress for sailing is layers. For northern tours, close to the skin, wear a moisture wicking layer, then an insulative layer (fleece, wool...), and an outer wind/water resistant layer. Waterproof shoes or rubber boots are an advantage on deck and for getting to and exploring shorelines and estuaries. Shorts and a bathing suit are great for a summer swim or hot spring soak. For life below decks bring casual and comfortable clothing. Don’t forget your favorite pair of slippers! We’ll send you a detailed list of what to bring when you submit your reservation.

What is the weather like?

The San Juan and Gulf Islands are known for their sunny summer days. We receive about half the rain of Seattle due to the rainshadow of the Olympics and Vancouver Island mountain ranges. Temperatures range from 55°-80° F in the spring, summer, and fall, and average 40°-50° F in the winter months. The Great Bear Rainforest of northern B.C. produces more variable weather. It’s not called a rain forest for nothing! Temperatures are usually in the 60s throughout our sailing season there. You will likely encounter a mix of sunshine with occasional rain during your trip, but you will stay warm and dry in our roomy pilothouse.

What time of year should I sail with you?

It depends on what you are looking for. April and May display an incredible abundance of spring flowers. Some areas are particularly spectacular with color at this time. The sunniest and warmest months of the year are July, August, and September. This is the best time of year to see the Great Bear Rainforest. October through mid-June offers the best sailing wind and the most quiet privacy in anchorages. We have had incredible trips in January! With our heating systems and all-weather pilothouse this time of year can be a magically peaceful and comfortable experience.

What if I get seasick?

Nearly all of the waters we sail in are well protected. Most people who are concerned about seasickness are pleasantly surprised that its not an issue for them on our trips. However, some of our trips involve making brief passages that can occasionally get rough enough to elicit this unfortunate gastronomic state. We recommend you speak with your doctor or pharmacist regarding appropriate motion sickness medication. In our experience for mild queasiness, the acupressure wrist bands, ginger tea or crystallized ginger (which we have on board), and staying above decks can be of great help. The good news is that after we’ve finished a rough passage, the seasickness disappears!

Are children welcome on your charters?

Absolutely! We love having children on board. It can be a hugely educational experience for them. There are many activities to keep them occupied, and enough new and exiting experiences to keep them talking about their trip for a long time. We do, however, prefer that if your child is younger that 10 that the guest list is filled by your party alone.

What is a “crewed” charter?

It’s a cruise that includes a captain and crew/chef who take care of all shipboard duties including safe navigation, local knowledge of choice attractions, and meals and cleaning. You can do as much or as little as you like. We are at your service!

Do I need to be in good shape?

No. The level of activity varies depending on the trip. However, anyone who can get in and out of the dingy and go for short walks will do fine. We have had mobility-impaired guests having wonderful cruises with us without ever leaving the boat! There are many beautiful things to see right from the cabin and deck!

What do your trips include?

All onboard meals, including select wines with most dinners. On some trips you will cover one dinner ashore. Your heated cabin includes a bed made with sheets, pillows, comforters, and blankets. Towels, cloths, shampoo, and soap are also complimentary. You are welcome to use the inflatable, kayak, and all fishing, crabbing, and shrimping gear. If you prefer to overnight at a place with moorage fees, you are responsible for them, as well as any fishing licenses, and most off boat tours.

How often do we get off the boat?

Rainforest we typically take the dinghy up a pristine river and go for a short walk, or explore a remote beach, or abandoned native village. In the San Juans and Gulf Islands many forest trails, beaches, and country roads await the happy wanderer.

What can I expect to learn?

Opportunities for education abound. Your skipper is a trained naturalist, and enjoys pointing out a special plant, and its traditional uses, or identifying an animal and explaining its habits. Local history and native culture are other subjects you'll learn about. The captain also enjoys teaching sailing to anyone interested. Our trips in the Great Bear and the Inside Passage incorporate Native guides who will lead you through abandoned village sites, and enthrall with tales of battles, ancient customs, and the history of the once mighty Kwakwak’wakw. Or take part in a traditional open fire salmon bake and learn of the rich past of the Heiltsuk. The boat makes a great platform for seminars and workshops. We also offer instructor-led cruises in subjects such as meditation, photography, and whale observation. Please see charter options. If you are an instructor interested in leading an art cruise feel free to contact us.

What areas do you charter in?

Our scheduled tours focus in the San Juans April through July, with one trip up the Inside Passage/Southern Great Bear Rainforest in early August, mid August to mid September in the Northern Great Bear Rainforest of the northern B.C. coast, and one trip down the Inside Passage/Southern Great Bear Rainforest in mid September. Please see our schedule. Any time you don’t see a scheduled trip booked the boat is open and available, so don’t hesitate to inquire.

What if I'm a solo traveler who prefers my own stateroom?

All of our rooms are double occupancy (View ship schematic), and allow for a maximum of six guests. If you prefer a private stateroom we will try to accommodate you. There will be an additional 50% fee if the tour is otherwise full.

Can you take more than six passengers?

By Coast Guard regulation, we can take up to six guests. On our instructional cruises, and with workshops and seminars, we can bring an instructor in addition to the six guests.

Do I need to know how to sail?

No. The captain and crew are perfectly capable of taking care of all sailing. However, you are welcome to participate at any time for your own enjoyment. The captain is a lifetime sailor, and would love to help you with your sailing skills. By the end of the trip you may just be ready for the America’s Cup!

Recent News

sailboat rental san juan islands

2023 Great Bear Rainforest Trip Recap

In mid-August this past summer, after a long pause of four years, we once again set sail for a nearly month-long journey up the enchanting Inside Passage. Beyond the towering mountain lined fjords, winding channels, and secret, pristine anchorages, lay…

sailboat rental san juan islands

2024 SEASON SCHEDULE IS OUT!

Ahoy sailors! We've just finalized our 2024 sailing schedule! For details about our trips please click on the date. Our day-sails are bookable securely online from the "Day Sail" page. To book or inquire about the multi-day sails please complete…

sailboat rental san juan islands

7 Amazing Getaways & Weekend Trips from Seattle

Visitors come from around the world to check out the sights in Seattle. They love touring the Space Needle, seeing the workers toss fish at Pike Place Market, and grabbing a cup of coffee from one of the local shops.…

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sailboat rental san juan islands

Boating, Sailing Tours, & Rentals

As a world-renowned boating destination, the San Juan Islands have an adventure for everyone. From day and overnight charters and rentals, to fuel and long-term moorage, you'll likely find what you're looking for. The San Juans are equally renowned for wildlife, especially whales. While out on the water, please follow the Be Whale Wise guidelines and help protect our spectacular marine wildlife. 

Tips & Resources for Boaters: If you want to maximize your enjoyment and boating safety in visiting the islands, you can find nearly 20 live-recorded educational webinars from the non-profit, America’s Boating Club of the San Juans . Review the  Green Boating Guide  from Friends of the San Juan Islands and explore the Maritime National Heritage Areas throughout the Islands!

sailboat rental san juan islands

Let us acknowledge that we reside on the ancestral lands and waters of the Coast Salish people who have called this place home since time immemorial and let us honor inherent, aboriginal, and treaty rights that have been passed down from generation to generation.  

Charters, Rentals & Tours

The shorter your stay in the islands the more important it is to plan ahead. Booking activities in advance will make your trip run smoothly and you'll be more likely to get your first picks! Most tour operators have generous cancellation policies in case you need to make changes. (Check with individual companies to be sure of their policies.)

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Reservations 800-617-2267

San Juan Island Boat Rentals & Tours

San juan island boat rentals & tours.

Travel & Leisure ranks the San Juan Islands as one of the top 10 island destinations in the U.S., in no small part because of the incredible boating opportunities found in our waters. Whether you are power boating or sailing, cruising in the San Juans offers secluded anchorages, unsurpassed natural beauty, abundant wildlife including Orca whales, and plenty of fun places to dock, quaff a pint of local craft beer, and dine on regional seafood.

There are three marinas located on San Juan Island. The Port of Friday Harbor Marina is the largest, providing year-round shelter with 500 slips and 100 slips for overnight visitors. You can make reservations for San Juan Islands boat rentals, tours, and sailing here in the summer months. Within walking distance of the town of Friday Harbor , the marina has easy access to restaurants, food markets, hardware stores, and other services. Fuel, Wi-Fi, potable water, an on-site laundromat, pump-out stations, and restrooms with showers are available at the marina. Boat rentals and tours are also offered at the Friday Harbor Marina. Boat owners and crews can make quick connections with scheduled seaplane service and passenger ferries to the mainland.

The Roche Harbor Marina at the north end of the island offers 377 slips for boats up to 100 feet in length and services such as fuel, power, a general store, pump-out, and showers. Roche is a great place to walk the docks and ogle mega-yachts and sloops, especially on holiday weekends.

The quiet Snug Harbor Resort Marina , on the west side of the island in Mitchell Bay, holds over 50 boats and is close to whale watching , fishing, and crabbing. You’ll need transportation to get from the marina into town and any services.  Other resources  for boat owners are the San Juan Island Yacht Club , and the Seattle Yacht Club , which has an outstation in Friday Harbor.

Boat Rentals and Tours

If you don’t own a water vehicle, never fear. The San Juan Islands have plenty of options for sailboat and powerboat rentals, as well as boat tour operators who’ll guide you on exciting high seas adventures. Most of the operators and rental outfits we mention are located on San Juan Island. Bellingham is also a popular port to book short and long cruises, and rentals in the islands.

Marine Parks and Trails

Once you’ve set sail in your vessel, or powered off in a boat rental, the Washington State Parks and Recreation System , of which the San Juan Islands are a part, has more than 40 marine parks and 8500 feet of public moorage for your boating enjoyment. As mentioned on their website, there is fishing galore, old forts to explore, clams and crabs to catch, and scenic trails to hike on your Salish Sea adventures.

The Cascadia Marine Trail  is an amazingly cool boating option. This water route traces some of the Puget Sound coves and inlets that originally marked a  Native American water trade system . The trail is primarily accessed from the water and is suitable for single or multi-day trips by canoe, kayak, motorized boats, or swimming if you’re an exceptionally hardy type. There are  66 campsites and 160 day-use sites .

For other ideas on where to moor your boat in the San Juans, take a peek at our blog post on The Best San Juans Islands Camping Spots for a Family Getaway.

Many thanks for the great photos to Sail the San Juans, San Juan Sailing, All Aboard Sailing (Ken Rea and Valerie Shore) and Friday Harbor Boat Rentals!

San Juan Sailing woman driving dinghy in the San Juan Islands

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San juan sailing.

Based in Bellingham, San Juan Sailing boasts a large fleet of sailboats and powerboats. They offer instruction, charters, guided flotillas to the San Juans, the Gulf Islands, and Desolation Sound, and if you become hooked, they’ll even sell you a boat!

Schooners North sailing Puget Sound

SCHOONERS NORTH

Go back in time and experience the history, adventure, and romance of sailing on a traditionally gaff-rigged wooden sailboat, the Spike Africa. From ½ day sailing charters to multi-day custom sailing excursions around the San Juan Islands, explore the Salish Sea and parts beyond. (Don’t forget your pirate attire).

Grand Banks in San Juan Islands

FRIDAY HARBOR BOAT RENTALS

With a small selection of powerboats, you can easily be your own captain cruising the San Juans. Or if you’re just getting your feet wet, try a half-day (4 hrs) or full-day (7 hrs) charter on a 32′ classic Grand Banks Trawler.

boy catching fish on boat rental

ISLAND BOAT RENTALS

Offering a fleet of 21′ welded aluminum boats with canvas enclosures and touchscreen navigation systems, this company rents out of Roche Harbor. The perfect way to spend a day in the San Juan Islands: fishing for salmon, crabbing, whale-watching, or island hopping.

Sail the San Juans Norhwind

SAIL THE SAN JUANS

Perfecting the art of “Slow travel” for over 25 years! Northwind is their new 55′ luxury sailboat, allowing you to experience either six- or twelve-day journeys through the San Juans or the Inland Passage in style. Enjoy kayaking, hiking, crabbing, then savor gourmet cuisine, from homemade pasta to seasonal blackberry cobbler. Sounds like the ideal vacation!

Sailboat Peniel with orcas in San Juan Islands

ALL ABOARD SAILING

Sail away for the day from Friday Harbor on the beautifully restored 42′ Pilothouse sloop, Peniel. The experienced husband and wife captains are well versed in both the dynamics of sailing in the PNW, local wildlife, and the local Orca whale community. Try a sunset dinner or photography cruise to make your island vacation something exceptional.

MORE ISLAND ACTIVITIES

A San Juan Island Must-See: The John S. McMillin Mausoleum

A San Juan Island Must-See: The John S. McMillin Mausoleum

It has a few names: Afterglow Vista, McMillin Memorial Mausoleum, and Afterglow Mausoleum, but one thing’s for sure: The John S. McMillin Mausoleum in Roche Harbor is a San Juan Island must-see.  Since you can probably have it to yourself in the colder months, we...

San Juan Island Bike Rentals and Tours

San Juan Island Bike Rentals and Tours

Make the most of your bicycling vacation to the San Juan Islands! Discover the best biking on the islands with links to maps, rentals, and guided tours.

San Juan Island Beer, Wine & Spirits

San Juan Island Beer, Wine & Spirits

Where to go on San Juan Island for some serious imbibing! An insider’s guide to sampling our best craft breweries, cider-makers, distilleries, and wineries.

San Juan Island Whale Watching Tours

San Juan Island Whale Watching Tours

Everything you need to know about orcas and whale watching in the San Juan Islands: take a tour, paddle a kayak, watch from shore – prepare to be amazed!

San Juan Island Kayak Rental & Tours

San Juan Island Kayak Rental & Tours

Paddle a kayak in the San Juan Islands and experience our remarkable wildlife and ecology from the water! Plus where to rent kayaks and go-to tour guides.

San Juan Island Hiking

San Juan Island Hiking

Discover San Juan Island’s best hikes from our resident hiking expert. From easy rambles to more strenuous treks, they all involve spectacular views!

San Juan Island Golf

San Juan Island Golf

A primer on San Juan Island’s scenic 9-hole links-style course. Two sets of tee boxes that play like a true 18-hole course. Challenging and fun!

San Juan Island Fishing

San Juan Island Fishing

The San Juan Islands are well-known for scenic beauty and whale watching, but talk to any Pacific Northwest angler, and odds are, the San Juans will be top of their list for excellent fishing.

The Best San Juan Islands Camping Spots for a Family Getaway

The Best San Juan Islands Camping Spots for a Family Getaway

Summer is almost here and for us, that means it's camping season, the best time of year! But why go camping in the first place? In some families, camping is a tradition that is passed on from one generation to another, singing the same goofy songs, having grandpa...

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San Juan Island Yacht Charters

Cruise the san juan islands with jamal charters.

sailboat rental san juan islands

The San Juan Islands are located within the Washington’s Puget Sound and are a destination for fishing, boating, sea kayaking, scuba diving, golf, and snow sports, with proximity to Seattle. Home to some of America’s most well-known corporations, Seattle is a growing city that is still a popular vacation destination.

SAMPLE ITINERARY: SAN JUAN ISLANDS

The San Juan Islands are made up of many islands of which 172 have names. There are 17 state parks within the islands. All of the islands are within two to three hours of cruising. The four main islands are Orcas, San Juan, Lopez and Shaw. It is a day’s cruise from the Seattle area to the San Juans. From Bellingham it is two to three hours. There are so many bays, harbors and anchorages that you could spend several summers cruising the entire area.

A typical ten-day cruise in the San Juan Islands would be as follows:

  • Day 1: Leave Bellingham Harbor and cruise to Sucia Islands. Drop anchor in Echo Bay. Sucia Islands are a cluster of 11 islands and inlets. Fossils can be found in one of the bays as well as oysters, clams & crabs. Hiking trails are abundant throughout the Islands. Sucia was known in the early days as the base for smuggling and rum running.
  • Day 2: Cruise to Stuart Island. There are two main anchorages on this island: Reid and Prevost Harbors. Anchor in one of these areas to explore the island on one of the hiking trails. There are picnic sites, docks and floats. A typical hike would be to Turn Point lighthouse, which has a sweeping view of the Canadian Gulf Islands and Vancouver Island. Both harbors are good places to practice your kayaking.
  • Day 3: Cruise to San Juan Island and Roche Harbor Resort, which is the famous home of the Roche Harbor Lime & Cement Company. This historical island provides many fun and interesting places to explore. The formal garden in front of the Hotel de Haro is quite beautiful. Besides a restaurant, bar, and shops, there is also an Olympic size swimming pool and tennis courts. The hike to the mausoleum is not to be missed. At sunset each night, we enjoy the traditional flag ceremony.
  • Day 4: Cruise to Westcott and Garrison Bays. Here we will crab, tour an oyster farm and visit the British Camp, which was established in the 1860s and remained active until 1872 after the Pig War. The blockhouse, commissary and barracks are still standing.
  • Day 5: Cruise to the town of Friday Harbor, the largest in the islands, which also serves as the county seat. There are all types of shopping available only a short walk from where the boat is anchored. Visit the Whale Museum or the University of Washington Marine Laboratories, located right in the harbor.
  • Day 6: Cruise to Spencer Spit State Park on Lopez Island. This beautiful sandy finger of land is perfect for picnics and hiking. Also, it is a great place to catch crab.
  • Day 7: Cruise the islands, looking for pods of Orca Whales (also known as killer whales) and do some exciting whale watching. Spend the evening in one of the dozens of lovely bays.
  • Day 8: Cruise to the beautiful and charming city of Victoria, British Columbia. Clear customs, sightsee, shop, enjoy high tea at the Empress Hotel and visit the Maritime Museum. Victoria is not to be missed.
  • Day 9: Cruise to Sidney Harbor and visit the famed and internationally known Butchart Gardens. Cruise to Sidney Spit Marine Park and enjoy a barbeque picnic on the beach. Hike around the island and see wild sheep, deer, pheasants and peacocks.
  • Day 10: Return to Bellingham.

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Welcome to San Juan Yachting

We don't try to be the biggest...but we passionately want to be the best.

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One of the most experienced, well-respected yachting schools in the Pacific Northwest and accredited by the Recreational Powerboat Association.

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With over 40 years of experience and 55 well-maintained sailboats and powerboats, our passion is to provide the very best bareboat charter vacation possible.

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Our brokers have logged a lot of sea time. They understand boats, value, and the individual client needs. Most of all, whether you are a seller or a buyer, they deliver.

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sailboat rental san juan islands

Roche Harbor Charters

​​​with outer island excursions.

Blackfish Express

Experience the San Juans aboard our high speed vessels, combining

Luxury and exhilaration..

Call us now to book the adventure of a lifetime:

360-376-3711

sailboat rental san juan islands

Custom Charters

Design the ultimate experience...

Fishing, island hopping, photography, fine dining, and lighthouse tours are just some of the possibilities for your custom charter. You can focus your trip on one activity or do a combination of activities on one trip. Give us a call to design a charter tailored to your group or book the vessel of your choice online now.

sailboat rental san juan islands

Perfect combination of comfort and thrill...

We are excited about our fleet of new, high-speed, and fuel efficient vessels. The fastest in the San Juans, the Blackfish Fleet can reach up to 50mph! With smaller vessels we offer an adventure where you can have a personal experience with your Captain and crew.

Triton

The possibilities are endless with a private, customized charter. Experience the islands in a whole new light as you cruise to islands the State Ferries can't go, catch and eat your own fresh fish or Dungeness crab, or explore the dramatic and diverse wildlife that our region has to offer. 

sailboat rental san juan islands

Plan It

Call our office and we can discuss all the various options for your custom tour. We can help you decide which vessel is best for your group and what activites you can do with the time you have. We are happy to design a charter for every budget.

sailboat rental san juan islands

Meet your Captain and Naturalist at Roche Harbor at the flag pole. We set out on every journey with your itinerary, but you direct the trip. We can be flexible to make your trip with us your most memorable experience in the San Juan Islands.

sailboat rental san juan islands

Orcas Island Sailing

  lessons and boat rental 360-310-0100 [email protected]  .

Boat rentals are available for a full day or half day.  In order to rent we ask that you have an intermediate level of boating experience.  We have 4 sailboats from 19 to 27 feet.

Prices vary based on boat.

BOAT RENTALS

Boat rentals are available for a full day or half day.  In order to rent we ask that you have a least an intermediate level of boating experience.  We have your choice of 3 sailboats, from 19 to 27 feet.

                Prices vary based on boat

SAILING LESSONS

Sailing lessons are private and personalized to you and your guests. They are available for a full day (6 to 7 hours) or half day (3 hours).  Rates include the boat, captain, and up to six passengers of your choosing.

half day rate..........................$575

full day rate...........................$1200

ABOUT ORCAS SAILING

We began with a simple idea which continues to be our guide to business today:  Provide a fun sailing opportunity for visitors vacationing in the San Juan Islands.

Because we don't charge per person you will experience learning how to sail in the company of your traveling companions rather than with a group of strangers.  This way you get a private charter for you and yours only!  Every skippered charter is hands-on.  You will be sailing the boat and learning the ropes!

Where we are

We are located at 1945 Obstruction Pass Rd, Olga, WA  98279

From Eastsound, drive south through Moran State Park.  At the Artworks building in Olga turn left onto Point Lawrence Rd.  Two intersections later veer right onto Obstruction Pass Rd.  At the end of this road is the county boat ramp and parking lot.  My office shack is adjacent to the boat ramp just inside the property of Lieber Haven Resort. Please call ahead as I am not often there.

From Doe Bay, turn left onto Obstruction Pass Rd then follow the directions above.

NOTE:  We are located at Lieber Haven Resort, in Obstruction Pass, at the end of the Obstruction Pass Rd.  We are not at Obstruction Pass State Park which is at the end of Trails Rd.

Ground Transportation

All forms of ground transportation can be easily arranged by calling Orcas Island Shuttle and Rental Car.  We encourage you to walk on the ferry!  Click  here  to go directly to their website or call 360-376-7433 for info

"My husband arranged this sailing lesson for our recent visit to Orcas Island. This was the highlight of my trip. My husband has been sailing for a few years and I am brand new to the sport. Nat was awesome. He was so patient with my lack of knowledge and/or recall of the limited knowledge I have. The bay was quite choppy when we headed out but I immediately felt very confident with Nat at the helm. Nat is very personable and is a great teacher. I highly recommend Orcas Island sailing.'"

Pacific Northwest Yacht Charters

San Juan’s Yacht Charters

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Know Here about the San Juan's Yacht Charters

Majestic. Awe Inspiring. Inspirational – A Magical Experience You'll Never Forget

San Juan's Yacht Charters is here to make your vacation unforgettable. The Pacific Northwest is home to a myriad of wildlife. It boasts diverse ecosystems, ranging from the mountain ranges to the numerous island and waterways and to the open ocean. The Pacific Northwest is home to bears, elk, mountain lions, eagles, salmon, giant Pacific octopus, whales, and many more! The highlight for most visitors is the resident and transient orcas, humpback whales, minke whales, and gray whales.

The waters surrounding the Pacific Northwest offer some of the most diverse whale and wildlife viewing on the west coast. There are only a few things more magical in this world than watching whales in their natural habitat. The regions across the world provide whale watching opportunities that are as diverse as the whale species. Humpbacks, 40-60ft. In length are found in waters surrounding Washington State and British Columbia while the playful black and white orcas live throughout the year in the waters of the Pacific Northwest's San Juan Islands.

We, at Pacific Northwest Yacht Charters , have luxurious San Juan's Yacht Charters and experienced guides who can educate guests about the specific whale's species during a whale watching tour. This can help you to have a memorable and unique experience for guests of all ages. The best time to go for whale watching at San Juan's Yacht Charters  is from April through September. Types of whales you can come across in the Pacific Northwest:

Southern Resident Killer Whales – Southern resident killer whales are some of the most researched whales in the world. They spend much of their time in the waters around Washington and British Columbia throughout the year feeding on their favorite food - Chinook salmon. This group of killers whales is very playful, acrobatic and at the same time social too.

Transient Killer Whales – Spotting transient orca whales in the waters of the Pacific Northwest is common due to an increase in their prey – harbor seals, California and Steller sea lions and harbor porpoise. Watching transient orcas hunt is very interesting and exciting! In the recent past, transient and bigg's killer whales have become more prevalent. They eat marine mammals: seals, sea lions, porpoise, dolphins – even other whales!

Humpback Whales – Over the last few years, humpback whales have made a comeback to the waters of Pacific Northwest in large numbers. Humpback whales are one of the most beloved and recognized whales in the world. Found in all the world's oceans, each humpback whale has a unique personality and appearance. If you're lucky enough you might spot mother humpbacks that nurse their calves with San Juan's Yacht Charters .

Minke Whales – Considered to be one of the most mysterious marine animals of the Pacific Northwest area, they are the most loved of all. Minkes are relatively solitary and spend their time feeding on schools of small baitfish. Minke whales can be found by smell alone - their breath is quite memorable! If you are lucky enough to catch a whiff, it is an experience that will long be remembered with San Juan's Yacht Charters .

Gray Whales – Currently, gray whales hold the record of the longest mammal migration as they travel from coldwater feeding grounds to the warm calving lagoons in Baja, Mexico. Gray whales are the only bottom-feeding whale, which means there are very rare instances that they will scoop up an entire mouthful of the sea floor. While they feed in the shallow, calm waters – it is indeed a sight to behold.

We at Pacific Northwest Yacht Charters, offer custom private tour experiences for couples, groups and families, with complimentary itinerary planning and personalized attention to detail. When on board your own Private Yacht Charter in Seattle , you get to spend more time with wildlife and less in transit. Your private and customized whale watching tour will guarantee the most authentic and personalized experience to you and your group.

The tours are hosted by knowledgeable and personable guides, dedicated to make your excursion a great one. We’ll take great care of you.

We can also provide yacht charters for other water sports activities such as Scuba Charter in Seattle , Fishing Charter Pacific Northwest , snorkeling and swimming to help you have a more memorable time in the Pacific Northwest along with whale watching at San Juan's Yacht Charters . The types of yachts vary as do your interest, and so it is the goal of Pacific Northwest Yacht Charters to align you with what suits you best. The cost of chartering each vessel varies and is dependent on the size and how long you will be chartering our vessel.

Contact us today to discuss your San Juan Yacht charter's requirements!

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Northwest Sailing Adventures 2024 Season Charter Rates

Sunset sailing with NW Sailing Adventures

6-day (5 night) Private Charter for 4: $2,700 per person (double occupancy)Boat total: $10,800

5-day (4 night) private charter for 4: $2,450 per person (double occupancy)boat total: $9,800, 4-day (3 night) private charter for 4: $2,200 per person (double occupancy)boat total $8,800, 3-day (2 night) private charter for 4: $1,850 per person (double occupancy)boat total: $7400, 2-day (1 night) private charter for 4: $1,250 per person (double occupancy)boat total: $5000, looking for a longer adventure: add $1,700 per day, 2024 season day sail rates.

Sunset sailing with NW Sailing Adventures

1-day: $185/hour (3 hour minimum, up to 6 guests)*

*Tax and customary gratuity not included.

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Book your dream vacation now!

Look no further than Northwest Sailing Adventures!

Terms and Conditions

Payment terms: We gladly accept cash, checks, money orders, or credit/debit cards (via PayPal).  All rates are based on US dollars. Exchange rate for Canadian guests will be determined at time of booking and is subject to change without notice.

A nonrefundable deposit of 30% of the total cost is required to confirm your booking. Remaining balance is due in full 30 days prior to departure.

If payments are not received on time, your booking may be cancelled and your deposit forfeited.

Cancellations less than 30 days prior to departure forfeit all deposits and you will be held responsible for payment of the full agreed fare.

If NW Sailing Adventures is forced to cancel, cut short, or reschedule due to circumstances beyond our control i.e. mechanical breakdown, illness, or emergency you will receive a full refund for all days not fulfilled under your charter agreement.

If your Captain determines that it would be unsafe to proceed or continue with your charter due to extreme weather, natural disaster, national emergencies, acts of God, or any other circumstance beyond the control of NW Sailing Adventures, 50% of your fare for all days not fulfilled under your charter agreement will be refunded.

A customary gratuity (tip) for your crew is always appreciated but is purely discretionary and not required nor expected. The following is a suggested guideline:

10% Service met your expectations

15% Service exceeded your expectations

20% Service far exceeded your expectations

Your crew is committed to providing you with the very best vacation experience. If for any reason you are less than satisfied with your experience, please let us know and every effort will be made to find a satisfactory remedy.

Bare-boat charters

More experienced guests may prefer a bare-boat charter.  We are happy to offer Diminuendo for your use. Please call for rates.

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Sail the San Juans

Make a Reservation (800) 729-3207

san juan islands cruises rates sail the san juans

San Juan Islands Sailing Charter Rates

We offer two booking options for our 6-day san juan islands sailing charters:.

1. Join-a-Cruise Charters – reserve your private stateroom and we will fill the other cabins on the boat 2. Private Charters – form your own group of up to six guests and have exclusive use of Northwind

Join-a-Cruise Charters: San Juan Islands (6 days)

Join a cruise charters allow you to reserve a private stateroom (or two) and then we fill the other cabins on the boat. This is a great way to meet other fun couples while enjoying the islands. Join a cruise charters are generally scheduled around the last week of each month, but as those weeks fill up we often open additional weeks. The itinerary is fixed and you must be an adult to join these trips.

$2895 per person$2995 per person

All San Juan charters begin on Sunday and end on Friday (6 days and 5 nights). All cabins are double occupancy. Singles traveling alone will always have a private cabin to themselves (50% surcharge). A deposit of $1000.00 per person is required on all 6-day charters. Balance due 60 days prior to departure.

Private Charters: San Juan Islands (6 days)

Private Charters allow you to form your own group of up to six guests and have exclusive use of the yacht. You may reserve any open week on our schedule and have a more flexible itinerary. If you can fill the boat with six people, then you benefit from a discount which is reflected in the 6 person rate option.

6 people.....$2695.00/per person6 people....$2895.00/per person
5 people.....$2995.00/per person5 people....$3205.00/per person
4 people.....$3745.00/per person4 people....$3995.00/per person
3 people.....$4595.00/per person3 people....$4895.00/per person
2 people.....$6295.00/per person2 people....$6695.00/per person

All San Juan Islands charters begin on Sunday and end on Friday (6 days and 5 nights). All cabins are double occupancy. Singles traveling alone will always have a private cabin to themselves (50% surcharge). A deposit of $1000.00 per person is required on all 6 day charters. Balance due 60 days prior to departure. Northwind is a non-smoking yacht.

View itinerary for this trip. View map of the San Juan Islands

Spring and Fall Sailing Season

Spring cruises run from May through June 15, 2024. Fall cruises run from September 15 through October 11, 2024.

Summer Sailing Season

Summer cruises run from June 16 through September 14, 2024.

6 people....$6045.00/per person
5 People....$6715.00/per person
4 People....$8395.00/per person
3 People....$10,295.00/per person
2 People....$14,195/per person

Take a fantastic voyage 150 miles up Vancouver Island on the Inside Passage to these magnificent cruising grounds similar to Norwegian Fjords. See snow-capped mountains, waterfalls, and world-class anchorages.

12-day charters along the Canadian Inside Passage depart Sunday return Thursday. U.S citizens only, valid passport required for this trip only. $2000.00 deposit per person required on all 12-day charters. Balance due 60 days prior to departure.

NOTE: We will also be offering a 12 day San Juan Islands trip for 2024. Contact us for more details

View itinerary for this trip View maps of the Inside Passage

Trip Details

Prices above include towels and linens, beverages, and all meals (except one dinner per week.) One Ocean Kayak is provided on the boat and a second kayak is available for a nominal charge. Due to insurance restrictions passengers must provide their own alcoholic beverages. Northwind is a non-smoking yacht. All departures from Bellingham, WA. All prices subject to change without notice.We accept VISA, MasterCard Discover or personal checks.

Sail the San Juans has a strict non-smoking policy during all operations of our charters. It is simply not possible to smoke aboard a boat without affecting others. This also includes all forms of e-cigarettes.

Reserve Your Trip Today!

For our free color brochure, questions, or to book your trip, please e-mail us at: [email protected] or call toll-free 800-729-3207 or 360-671-5852

Last Minute Discounts

From time to time we offer special discounts on our trips. Sometimes we have a spot for one couple left open on a “Join a Cruise” trip or we have had a last minute cancellation and we would like to fill that spot. We offer last minute discounts from 10-15%. If you are available 30 days or less prior to departure, these might be of interest to you. Call to be put on our waiting list for last minute openings.

Reservations are required at least 30 days prior to sailing.

Weekly departures on Sunday at 2:00 PM from Gate 12, Bellwether Way Located in beautiful Squalicum Harbor in Bellingham, Washington.

For reservations and more information please call us at: 800-729-3207

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Trip duration, multiple days (less than 1 week), weekly trip show boats that have weekly prices. most weekly boats outside of the us are available only saturday to saturday., boat length: 5ft -, manufacturer, boat build year: -, weekly trip, price: $ - $, 41 boat rentals in san juan, puerto rico: yacht charters.

The best party boat in San Juan Bay, Puerto Rico

In addition to the best offers we have for boat and yacht charters in San Juan, Puerto Rico, see also options available for rent in these nearby locations:

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Rent a Private Boat Charter in San Juan with Sailo

Looking for a boat rental in San Juan, Puerto Rico? With Sailo, you’ll find a great choice of private boat charters in San Juan, Puerto Rico for everything from a day trip through to a longer sailing vacation. If you’re visiting old San Juan boat tours with friends or family, you’ll find ample choice to try San Juan water tours with Sailo. Step aboard your own private boat charter in San Juan Islands and discover this amazing sailing location!

Our prime selection of private yacht charters in San Juan, Puerto Rico

Want to rent a boat in San Juan, Puerto Rico? You’ll find 3 boats waiting for you to take them on an adventure here on Sailo. Choose from our line up of TOP San Juan sailboat charters . Prefer catamarans? No problem…. Sailo currently has catamaran rentals in San Juan . Want to see Puerto Rico in style? One of our motor yachts in San Juan will fit the bill. If you’re planning a big party or event with over 12 people, you can also choose from our party boats in San Juan for an incredible day on the water.

How to find the right boat cruise among San Juan yacht charters

Renting a boat in San Juan, Puerto Rico has never been easier! When searching for a boat rental in San Juan, make sure to include your dates, trip duration and number of guests to get a first accurate selection of available charters. Daily experiences last for 2, 4 hours or a full day. You may further personalize your results by choosing the type of boat you’d like to rent, your price range and whether you want to hire a captain or you’re interested in a bareboat. Click on the boat rides in San Juan you like to get to the next page where you can view more photos, read the boat description and the reviews to see if it's the right fit for your old San Juan boat tours. You can always message the owner if you have any questions about their boat or you want to make special arrangements.

How much does it cost to rent a boat in San Juan, Puerto Rico for a day?

The best Sailo deal for daily boat rentals in San Juan, Puerto Rico starts at $250. The average price for a daily San Juan boat cruise is $1100, making it the best choice for a private sunset cruise, a sightseeing tour or an action-packed day on the water with family or friends! For those of you who are looking to splurge, check out our luxury yacht charters in San Juan with prices up to $6500 (service fee and mandatory extras not included).

San Juan Island boat rentals: Do I need a licence to rent a yacht on Sailo?

No, you do not need a license to charter a yacht in San Juan Island on Sailo as long as you are renting a boat with a captain included. There are two types of boat tours in San Juan, Puerto Rico available on our website: bareboat and captained charters. If you rent a bareboat yacht, then your charter comes without any crew, and you or someone in your group will need a license. The boat owner will require you to upload the boating resume or license of the person who will drive the boat. Most of our boat owners might also like to test your boating skills before you take your bareboat charter out on the water. When you charter a yacht in San Juan with a captain included or add the captain and/or crew as an extra to your sailing adventure, then a certified skipper will be provided.

Responsible boating guidelines

However long you’re on a boat, it’s always a thrilling and fun experience. Here at Sailo, we like to make sure that the stunning beauty of the seas, lakes and rivers of our planet stay as pristine as possible. If you’re going to charter a yacht, from a few hours to week, try to follow these sustainable boating tips:

  • Take your rubbish home
  • Use eco-friendly sunblock
  • Avoid single use plastic

Much of the world’s plastic ends up in the sea, so reduce, reuse and recycle. Read more about responsible boating.

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"10 Days of Charter for the Price of 7 Days" Special! A 43% added value!

Available on select charter start dates: 3/20, 3/30, 4/10, 4/20, 5/1, 5/11, 5/22, 6/1, 6/12, 10/5. click here for details..

Power Fleet
Vessel Information 2024 Dates and Rates
Summer
6/8 - 8/30
Late Spring
4/20 - 6/7
Late Summer
8/31 - 9/20
Early Spring
3/16 - 4/19
Fall
9/21 - 10/14
Daily Hull Damage Waiver Liability
Coverage
Listed rates are for a charter week of 7 days and 6 nights (usually 9AM Saturday to noon Friday). Daily Damage Waiver and Liability Coverage rates discounted for multiweek charters.
Motoryachts

Navigator 51 - 3 Staterooms
Free training offer!
Progressive Thrusters, Solar, Starlink!
9950
Trawlers

Seahorse 52 - 2 Staterooms
Free training offer!
Stabilizers, Solar Panel, Starlink Internet!
10500

North Pacific 49 - 2 Staterooms
Starlink internet!
Free training offer!
11925

American Tug 435 - 2 Staterooms
Starlink Internet!
9600

Nordic Tug 42 - 2 Staterooms
2025 Alaska Opportunity!
Starlink & Solar! Bow & stern thrusters!
8825

Grand Banks 42 - 2 Staterooms
Bow & stern thruster!
7800

Selene Europa 42 - 2 Staterooms
New to the fleet in 2024!
Starlink Internet!
7800

Helmsman Trawler 38E - 1 Stateroom
Solar panels!
6425

Nordic Tug 37 - 2 Staterooms
Solar and Starlink!
6575

American Tug 362 - 2 Staterooms
Starlink Internet!
6625

American Tug 365 - 1 Stateroom
Sleeps 4, Washer/Dryer. Starlink!
6175

American Tug 34 - 1 Stateroom
Solar panels & Starlink!
Same length & floor plan as the AT365.
5825

Ranger Tug 31CB - 1+ Stateroom
5300

* NOTE: $20/day provides you and each member of your crew with a total of $1,000,000 personal liability coverage during your charter.

Discounts available for multi-week (2+) and for multiboat (3+) charters. For details and off-pattern rates please visit our charter FAQs.

Special Opportunities

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Courses & Stateroom Bookings Summer Guided FlotillasSpring & Summer Guided Flotillas Fall Guided Flotillas

T. 360-671-8089 (charter) | T. 360-671-8339 (school) | T. 360-671-0829 (brokerage)

2615 South Harbor Loop, Suite 1, Bellingham, Washington 98225

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©Copyright 2022 San Juan Yachting | All Rights Reserved | This Website was Handcrafted by the Staff at San Juan Yachting

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Island Boat Rentals

rental boat, roche harbor, san juan island

Island Boat Rentals offers 21' welded aluminum boats with canvas enclosures and touchscreen navigation systems as well as a 16' welded aluminum open skiff with side console and navigation system.  We are located at Roche Harbor on San Juan Island (just 10 miles north of Friday Harbor).  Call 360-317-6160 for reservations or more information.

sailboat rental san juan islands

Island Boat Rentals is owned and operated by Scott and Barb Leeming.  They opened for business in 2014 with support from their son, Will.

sailboat rental san juan islands

   ABOUT OUR BOATS:

Our 21ft welded aluminum “Thunder Jets” with seating for 6 passengers have 90 hp Yamaha 4 stroke engines. 

Our 16' "RiverHawk" open skiff offers seating for 4 passengers and has a 50 hp Yamaha 4 stroke engine.

Our boats are PERFECT for fishing, crabbing, island exploring and wildlife viewing. All of our boats are equipped with GPS navigation systems as well as all the safety equipment required by the USCG. We picked Thunder Jet and RiverHawk boats because they're safe and durable, and both companies are leaders in the innovation of aluminum boat technology.

sailboat rental san juan islands

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sailboat rental san juan islands

Washington’s Island Getaway: How to Do the San Juan Islands

W hen thinking about a trip to the Pacific Northwest, islands aren’t the first thing that come to mind. Forests, mountains and lots of rain are more stereotypical. So while visitors might not be as familiar with the San Juan Islands, located just off the coast of Seattle , locals flock to this beloved archipelago every summer to take advantage of the rare sunny days in the region. Accessible only by ferry, private boat, or small local airlines if you prefer a scenic (but expensive) sea flight, anyone who’s spent part of their summer here will vouch that this remote haven is one of the most beautiful places in the world. 

Honestly, it’s a little bit of a hassle to get there, but completely worth the experience once you arrive. Technically, there are close to 200 islands in the archipelago , but visitors frequent four main islands: San Juan Island, Orcas Island, Lopez Island and, sparingly, Shaw Island. San Juan and Orcas are the largest by far, and receive the most visitors, particularly during the summer months. But if it’s your first time heading out to the San Juans, you’ll need some pointers, so here’s a complete rundown of exactly how to get there, which ones to spend the most time at and what to do once you get there.

But First, Overnight in Seattle

No matter what your plans, getting to Seattle for a day or two first is a good idea. For one thing, the Anacortes Ferry Terminal is a two- to three-hour drive from the city. For another, most of the ferries leave early in the day and require arrival at least a half hour before departure. After a long flight, or even a short one, getting directly into a rental car and driving to the ferry makes for a pretty long travel day. Even if you’re trying to squeeze in a weekend trip, pad in an extra day (or two) to spend in the city as a buffer with the rest of your travel, preferably at one of these hotels. Sprinting toward a ferry as it departs is not a good feeling, as I may or may not have learned from firsthand experience. 

The Edgewater

The Edgewater’s claim to fame is that it’s Seattle’s “only over-water hotel” — it’s literally built over Puget Sound and affords the kind of stunning waterfront views people will always pay top dollar for. The other rather wonderful claim to fame at this property is its connection to The Beatles — yes, the actual Fab Four stayed here during their first world tour in 1964. They rather infamously “fished” out their hotel room window, and allegedly even caught something. If you had any doubts about how close it is to the water, let that anecdote put them to rest. Grab dinner at their waterfront restaurant, Six Seven , and hang out in the cozy, cabin-like bar for a nightcap, or just have that drink on your own waterfront balcony. 

Thompson Seattle

If you’re only here for a night or two, why waste time? Thompson Seattle is right in the thick of things. You can walk to Pike Place Market and the world’s oldest Starbucks, and stand in line to get…your regular coffee order, then stroll over to the Gum Wall to get a very gross but necessary selfie. Wander through Pike Place and either pick up some local snacks from the vendors or head off into one of the cafes for a bite to eat. If you can brave the lines, Pike Place Chowder will not disappoint. If you don’t end up eating at the market, the hotel’s own rooftop bar, The Nest , offers stunning views of Puget Sound and the Olympic Mountains, and the ground floor restaurant, Conversation , focuses on fresh, local seafood and farm-to-table sourcing.

You Are Here: Seattle

Getting to the san juan islands by ferry.

Leave plenty of time to get to the Anacortes Ferry Terminal. If traffic is clear, it should only take two hours from Seattle, but with traffic it can be up to three. Once you get to the terminal, lines are likely, so plan to be there at least an hour before your allotted departure time. If you arrive at the check-in less than 30 minutes before departure, they will not let you board. No exceptions, so plan wisely! All four of the main islands are accessible by ferry from the terminal, and there’s also an airport shuttle to the terminal if you opt not to drive or stay over in Seattle. 

The islands themselves are fairly remote, so securing a car is highly recommended, especially for first-time visitors. By and large, most people get to the islands by ferry, and that’s partially because the islands are not walkable. Even the most populous one, Orcas, is made up of different enclaves that are all about a half hour away from each other. There are taxis and Ubers sparingly available, but for adventuring, exploring and general peace of mind, it’s best to have a vehicle. 

If you’re in a car, you will need to make a ferry reservation before arriving at the terminal via the Washington State Ferries website . Reservations for the summer through September, the high season, initially open up two months before the start of the season in late April. This is the best time to make a reservation, as more are released two months before every sailing date, and also two days before, but there are far fewer slots. If you can’t get a reservation, it is possible to travel standby, but space is never guaranteed this way. Reservations are free to make, and can be canceled without charge up to 24 hours before. Reservations should be made for both the westbound trip (toward the islands) and eastbound back to Anacortes.

Once you arrive at the ferry terminal, trade your reservation for a ticket, which is about $50 for a car and driver, plus $15 per passenger, so a round-trip ticket for two people is around $65. Since this is much cheaper than a flight, and the ferry ride itself is around an hour, which is about as long as the flight, the ferries reign supreme. And despite a little inevitable hassle and confusion, once you’re onboard, there’s food and drink, alcohol and plenty of views, like the occasional whales (orcas), dolphins, sea lions and more.

Pro tip: If you do cross the ferry without a car, there are rental cars available on the island right at the ferry terminal. Then again, current demand indicates these will be expensive and are likely to book up.

Getting to the San Juan Islands by airplane

San Juan Airlines and Kenmore Air are the two carriers who regularly fly to the San Juan Islands. San Juan Airlines operate land planes and one-way tickets start at $114, but their terminal is located in Bellingham, so it’s still about an hour and a half drive from Seattle, and travelers are required to pay for parking for more than 36 hours. Kenmore Air operates both land and seaplanes, and departs from several small airports throughout Seattle, which means travelers can skip the drive. Both airlines have frequent flights to Eastsound on Orcas Island and Friday Harbor on San Juan Island, and they also offer private charters aside from scheduled flights. Rates fluctuate quite a bit based on season and booking time frame, so it’s best to connect with the airlines directly.

Visiting Orcas Island

By far the most popular and bucolic of all four islands, Orcas is the perfect place for a first-timer or newbie to begin exploring. At 57 square miles, there are multiple settled areas throughout the island, but Eastsound is the central village closest to the ferry, and the Outlook Inn is hands down the best hotel in the area. A historic property built in 1876 by Charles W. Shattuck (a homesteader who’s affectionately referred to as “the founder of Eastsound”), the building changed hands many times before settling into its contemporary iteration in the 1970s when the current owners acquired it. Columbia Hospitality , who rep a number of boutique properties in the region, took over management and operations in 2022.

Sleek white and grey interiors make the Outlook Inn’s Water’s Edge and Bay View suites the most desirable rooms on the island, as do their proximity to the water. Water’s Edge suites are, as the name suggests, right on the shoreline and separated from the main building, and Bay View suites have private balconies and unobstructed waterfront views. The inn’s own New Leaf Cafe also has waterfront views and a hyper-seasonal menu highlighting Pacific Northwest farmers and purveyors. The hotel is just a block or two from the center of town, where freshly made pastries at Brown Bear Baking and oceanfront snacks at The White Horse Pub were highlights for casual dining. On the higher-end side of things, local tasting menus at Houlme or Matia Kitchen are available Thursday to Sunday. 

Outside of Eastsound, other parts of Orcas worth exploring include a drive out to Buck Bay Shellfish Farm , for caught-this-morning seafood of all kinds: oysters, shrimp, crab, halibut, salmon, clams and whatever else came in with the tide. Around another side of the island, Doe Bay Resort boasts clothing-optional hot springs and sauna , and down at Deer Harbor, sign up for a day of learning to sail with Captain Ward at Northwest Classic Daysailing . Ward has been sailing around the islands for the past two decades, and his classic 1948 wooden sloop Aura is available for booking May through October. When you’re out with him, the captain will let passengers actively sail the boat, so get ready to be put to work. He’s also incredibly knowledgeable about the history of the area.

Another recommended water activity is guided sea kayaking with Shearwater Kayak Tours , and while you’re on land, a relatively easy hike up Mt. Constitution affords views of the islands for miles. Down in Rosario, yet another Orcas community, touring the historic Moran Mansion (now a museum) is another must. Self-guided tours are available daily from 8 a.m. to 8 p.m. during the high season. Once you’ve seen all there is to see on Orcas, it’s time to take a couple day trips to the other islands. 

Visiting San Juan Island

Roche Harbor and Friday Harbor are the two central hubs on San Juan Island, although the ferry only lands at Friday Harbor. The commercial hub for the San Juan area, Friday Harbor isn’t quite as beautiful or remote as some of the other areas, but it does boast an incredibly scenic lavender farm. Visiting the Pelindaba Lavender Farm is free, and given its location right on the water, photos from this particular site are usually very epic. For the foodie side of things, make your way over to the other side of San Juan and visit Westcott Bay Shellfish Company in Roche Harbor. Their Tide Tables picnic area is literally at the water’s edge, and you can watch fishermen catch and shuck (and grill) the oysters that make their way to your table. Barbecued with various compound butters, these oysters are so good they’ve even been known to convert avowed oyster haters.

Visiting Lopez Island

Lopez is great for a day trip, but there isn’t enough to do here to warrant an overnight stay. Much smaller than either Orcas or San Juan, one thing Lopez Island is known for is its food. In fact, ice cream from the Lopez Island Creamery is so popular that it’s exported to the other islands — you can find it all over the San Juan area. But since you’re there, why not go to the source? Pints, ice cream sandwiches and ice cream pies are all on offer, and they make most of their products with solar power, just another reason to support.

Other things to check out on “Slopez,” the most laidback island of the bunch, include the ramen, gyoza and udon at Setsunai Noodle Bar , local, plant-forward dishes at Ursa Minor , and don’t forget to grab a loaf of bread at Barn Owl Bakery , where they use wheat grown and milled on Lopez with machinery from the 1800s. 

Visiting Shaw Island

Known as “ the holy island ,” most visitors drawn here are intrigued by the nuns who inhabit the isle , which is just 7.7 square miles. As the smallest of the four main islands, Shaw has a population of fewer than 200 people year-round. As such, there are no hotels or rentals available, but there is one grocery store, Shaw General Store , and one park and campground area . 

If you’re kayaking or hiking around the island, Shaw could be a good place to crash for the night, otherwise it’s good for an afternoon trip, and particularly good for boaters, who like the peace and quiet. Indian Cove is the perfect place to moor if you’re boating, as it’s also next to the 60-acre Shaw Island County Park, where pristine beaches and abundant tide pools make for an idyllic afternoon.

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The post Washington’s Island Getaway: How to Do the San Juan Islands appeared first on InsideHook .

The San Juan Islands in Washington at sunset. Our guide to the Pacific Northwest area includes information on the four main islands: Orcas, San Juan, Lopez and Shaw.

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  24. Washington's Island Getaway: How to Do the San Juan Islands

    San Juan Airlines and Kenmore Air are the two carriers who regularly fly to the San Juan Islands. San Juan Airlines operate land planes and one-way tickets start at $114, but their terminal is ...