Waypoints Yacht Charters logo

  • Find Us On Facebook
  • Find Us On Instagram

New Model Charter Yachts In Annapolis, MD

Waypoints Annapolis offers a variety of new model sailing monohulls, catamarans, and powerboats for multi-day charters on the Chesapeake Bay. Our team prides itself in providing an elevated charter experience for each of our guests aboard our meticulously maintained yachts equipped with all of the comforts of home. Come charter with us and discover the Waypoints difference.

Notice of Use of Cookies

We use cookies and similar technologies to recognize your repeat visits and preferences, as well as to measure the effectiveness of campaigns and analyze traffic. To learn more about cookies view our Privacy Policy . By continuing to use our site, you consent to the use of cookies.

Sign up and

GET 20% OFF

Your first boat rental

Welcome to Sailo !

Your code is:

Enjoy 20% off

  • Explore boats
  • Text +1 910-447-2456 Call +1 910-447-2456

Departure date

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: $ - $, 1 catamaran rentals in annapolis, md.

Luxury Sailing Catamaran

Annapolis, MD

boating guide

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

  • 25 boat rentals in Annapolis, MD
  • 25 boat rentals in Parole, MD
  • 25 boat rentals in Highland Beach, MD
  • 25 boat rentals in Arnold, MD
  • 25 boat rentals in MD
  • 25 boat rentals in Edgewater, MD
  • 25 boat rentals in Riva, MD
  • 25 boat rentals in Severna Park, MD
  • 12 boat rentals in Stevensville, MD
  • 25 boat rentals in Shady Side, MD

Renting a boat is the perfect way to explore Annapolis, MD

Rent a yacht in Annapolis to see this stunning location like you’ve never seen before. With a private boat rental from Sailo, you and your family or friends will have the freedom to discover some of the most beautiful parts of Maryland. Whether you choose a sailboat, catamaran or a motorboat, you are in for a thrilling, romantic and unforgettable adventure aboard your private yacht charter.

Curious about your options for renting a catamaran in Annapolis, MD?

Are you looking for a catamaran to rent in Annapolis, MD? We’ve got your covered with a total of 27 waiting for you at the dock. Available with or without captain, these amazing charters are the best way to enjoy the coastal scenery during the day, a breathtaking sunset or a day full of fun in the water with family or friends. Rent a private catamaran charter in Annapolis and get ready for a great experience in the waters of Maryland.

Amazing yachting experiences happen on the right boat. Search for it now!

Choosing the perfect Sailo boat for you in Annapolis, MD is easy and quick thanks to our advanced filters! First we recommend filtering by date and trip duration. Whether you look for a 2, 4 hrs or a full day rental in Annapolis, the group size is very important, as well as the type of boat you want for your adventure in the waters of Maryland. Use the price filter to see only options according to your budget and click on the 'Crew' button to choose if you want a boat with a captain or you want to drive it yourself (option Bareboat). Once a Annapolis charter catches your eye, click on it to see the boat page with more photos and a detailed description. Check the reviews and send a direct message to the boat owner to ask more details!

How much does it cost to rent a yacht in Annapolis, MD for a day?

Boat charter prices in Annapolis, MD vary significantly. You can find great budget friendly rentals starting from €250 for a daily trip. Luxury or party yacht rentals for the day can cost up to €6500 where service fees and mandatory extras are not included. Your budget per day will vary depending on whether you are renting the boat in Annapolis with captain and/or crew, fuel cost, special requests for pick-up and drop-off or other special arrangements you may want to make with the owner.

If I rent a yacht on Sailo, will I get insurance coverage?

Yes, all Sailo boats available for rental have insurance: sometimes included in the price, other times available to buy as mandatory extra.

Together we protect our oceans

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.

Check our sailboat rentals in Annapolis !

  • FAQ and Policies
  • Accessibility Statement
  • Boat Rentals
  • Boat Calculator
  • Discover Boating
  • Community questions
  • Referral Program
  • Vivre: Furniture & home decor
  • British Virgin Islands
  • La Paz, Mexico
  • Cabo San Lucas, Mexico
  • Key Largo, FL
  • St. Vincent and Grenadines

ASA Sailing School

  • Chesapeake Bay Itineraries
  • Key West Itineraries
  • Chesapeake Bay
  • Virgin Islands
  • St. Vincent & The Grenadines
  • Browse our Fleet
  • Meet Your Captains
  • Charter Management
  • Sailing Lessons

Sail Away Catamarans

Chesapeake Bay Boat Rentals

We provide gorgeous sailing catamaran Chesapeake Bay boat rentals. Your catamaran will be waiting for you at Liberty Marina on the South River. From there you and your guests will set sail and enjoy the many wonderful destinations the Chesapeake Bay has to offer. Our private sailing cruises are customized for each guest, so you can spend a half day, full day or have an overnight adventure on your yacht. Browse our most popular itineraries to get you started, or send us a booking request and let our experienced charter agents help you design a one of a kind experience!

Our Chesapeake Bay Fleet

Sailing cats.

Catamaran Fountaine Pajot Saba 50 Quintet

Fountaine Pajot Saba 50

catamaran charter annapolis

Seawind 1370

catamaran charter annapolis

Kalm Waters

Fountaine pajot helia 44.

Seven Day Weekend Catamaran

Seawind 1160 Lite

Go Slow Catamaran

Shared Adventure

Current charter rates.

Chesapeake Bay Season: July 1 - Oct 27

Boat 4 hrs 6 hrs 8 hrs 2 days 3 days 4 days 5 days 6 days 7 days Cleaning Fees
Nanyehi$1,300$1,600$1,800$3,200$4,500$6,000$6,500$7,800$8,000Single Day: $250
Overnight: $350
Shared Adventure$1,300$1,600$1,800$3,200$4,500$6,000$6,500$7,800$8,000Single Day: $250
Overnight: $350
Williwaw$1,800$2,160$2,400$4,320$5,760$7,680$8,400$10,080$10,560Single Day: $300
Overnight: $500
Kalm Waters$1,800$2,160$2,400$4,320$5,760$7,680$8,400$10,080$10,560Single Day: $300
Overnight: $500
Stay Tuned$2,100$2,300$2,500$4,200$5,500$7,400$8,250$9,900$10,360Single Day: $300
Overnight: $500
Damselfly$2,200$2,400$2,600$4,400$5,850$7,800$8,400$10,080$10,850Single Day: $300
Overnight: $500
Smack$2,400$2,600$2,800$4,680$6,240$8,320$9,100$10,920$11,440Single Day: $350
Overnight: $550

Captain Rates

Charterer pays the Captain/Instructor directly at the end of each Charter, separate of the Charter Contract fees.

*Gratuities for charters are generally discretionary, but they are an important way to show your appreciation for the crew's hard work and dedication during your trip. As a general guideline, the average crewed charter tip to the crew is 15-20% of the charter trip base price, depending on the level of service provided and your overall satisfaction with the experience.

Chesapeake Bay Attractions

Annapolis, Maryland, USA downtown cityscape on Main Street.

Historic Downtown Annapolis

Known as America's Sailing Capital, Annapolis has 500 miles of gorgeous shoreline to explore. Annapolis has more surviving 18th century buildings than any other city in the United States. Visit landmarks like the The State House, the United States Naval Academy and many more historical sites, museums and monuments. Stroll along the historic downtown streets and visit unique shops and art galleries.

Waterfront Dining

Famous for it's crab cakes, a true Annapolis experience is not complete without a lunch-stop at one of the many waterfront restaurants along your sailing cruise. Kentmoor Restaurant and Crab House and Mike's Crab House are just few of the boat-friendly restaurants in Annapolis.

Kentmoor Restaurant Waterfront Dining by Boat

Chesapeake Bay Lighthouses

Over 30 lighthouses still stand on the Chesapeake Bay. Take your Annapolis sailing charter to cruise past your favorites, including the Thomas Point Shoal Lighthouse, the most photographed lighthouse in the world!

Quaint Towns Nearby

An overnight sailing cruise is the perfect way to enjoy beautiful towns nearby, like Oxford, Rock Hall and St. Michaels to name a few! They each offer charming dining, shopping and scenery.

st_michaels

Classic Sail Charters

Sailing Charters in Annapolis, MD

Classic Sail Charters offers Chesapeake Bay sailing adventures on our thoroughly refined sailing yacht, the Licentia. It is exquisitely appointed, safe, and ready for you to call home while you enjoy the mystique and allure of some of the best sailing grounds in the world.

Select A Time

1 - 6 people | 3-hour (am/pm) - 2.5-hour (sunset) sailing yacht cruise | 25% deposit, minimum age: 7 years., gratuity not included in pricing.

  • Most Popular!
  • Users Up to 6 Passengers
  • Hour Glass 2.5 Hours

Sunset Sail - Licentia

Come join us for an unforgettable cruise on one of our world-class sailing yachts and enjoy the beautiful sunsets in Chesapeake bay!

  • Hour Glass 3 Hours

Morning Sail - Licentia

Classic Sail Charters offers Chesapeake Bay sailing adventures on a thoroughly refined sailing yacht Licentia, a 2008 Catalina 42 MKII.

Afternoon Sail - Licentia

Come sail with us on the Chesapeake Bay! As the largest estuary in the world, the Chesapeake Bay is stunningly beautiful!

Other Times

  • Hour Glass 8 Hours

Full Day Sail - Licentia

Come sail with us on the Chesapeake Bay! As the largest estuary in the world, the Chesapeake Bay is stunningly beautiful, fed by countless navigable rivers and home to an abundance of wildlife.

Chesapeake Bay - Annapolis

Looking for a unique sailing experience on the Chesapeake Bay? Our charters are the perfect way to explore the Bay and its navigable rivers. As the largest estuary in the world, the Chesapeake Bay is a natural beauty filled with an abundance of wildlife. Create your own sailing adventure on the Chesapeake Bay as we work with you to define your perfect excursion and then you may leave the rest to us!

Annapolis, located less than an hour from Washington, D.C., is noted not only as the location of the US Naval Academy but as America’s ‘Sailing Capital.’ It is home to a rich history that includes the oldest working state capitol building in the U.S., noted as the location where General Washington resigned his commission, as well as dozens of first-class bed and breakfasts, hotels, and fantastic restaurants. As a sailing venue, it is second to none.

catamaran charter annapolis

CATAMARAN EVENT CHARTERS  

Private day-charter on our catamaran for bachelor/bachelorette parties, birthdays, anniversaries, company functions or any other occasion.

Image

Luxury Catamaran & Yacht Charter in Annapolis

Home Luxury Catamaran & Yacht Charter in Annapolis

Got questions? Call us at 561-900-6016

Looking for the best day on the Chesapeake Bay? We are fully equipped with full kitchen essentials, a grill, a bathroom, private changing room, a large covered stern table and an outdoor HOT water shower. There is a high quality sound system throughout the vessel including the bow you can connect to. This is a very spacious catamaran with lots of room to lounge up front on the trampoline or hang out on the dive platform in the back. Up to 12 passengers MAX.

You are welcome to bring your own food and beverages however we also work with a local concierge service if you’d like the boat stocked for your event. We provide ice, water, and and a large cooler you may use.

**Captain, 2 crew & fuel included in all charters. We cater to you!**

All Charters includes use of:

2 Paddle boards

5 Bote inflatable bow chairs

7×7 Floating dock

Blow up floats

1 full hammock

Coyote gas Grill

Fresh water shower (indoor & outdoor)

Ice included

Drink fridge

Sound system connect via bluetooth

We now offer tubing! You can add while onboard. 

*Gratuities not included

catamaran charter annapolis

Elite Charters of Annapolis

Luxury yacht charter experiences.

Unique and Unforgettable Memories Await in Annapolis and on the Chesapeake Bay

Why Choose Elite Charters of Annapolis

boat docked at a restaurant in Annapolis

Exclusive Yacht Charter Experiences

Let us host your next special occasion, cocktail cruise, relaxing weekend, or wedding cruise aboard one of our luxury yachts.  

Located in the heart of Annapolis, our professionally crewed charter yachts are easily accessible and create stunning and memorable experiences on the Chesapeake Bay. 

Our yachts are equipped with state-of-the-art amenities, including air conditioning, comfortable seating, and entertainment systems.

Professional Captains and Crew

Our crew members are experienced and knowledgeable about the Chesapeake Bay. They will ensure that you have a safe and memorable experience on your charter.

Muse - 87' Warren Yacht

  • This sleek 87 ft sport yacht is available in Annapolis and the Chesapeake Bay.
  • Invite up to 12 guests for half or full-day private yacht charters.
  • She boasts beautiful teak decks, dual salons, and a spacious aft entertainment area.
  • With a 5 ft draft, Muse can navigate secluded coves and anchorages.
  • A 27-knot cruise speed ensures fast travel and exploration of multiple destinations.
  • Overnight guest accommodations for six plus crew.

Shredder - 54' Eastbay

  • Built by Grand Banks, the 54 ft Shredder is the quintessential Downeast-style cruiser.
  • Accommodates up to 12 guests for half or full-day private yacht charters.
  • Ideal for multi-day or week-long luxury Chesapeake Bay cruises for a couple in the spacious master stateroom.
  • Perfect for day excursions to quaint Chesapeake Bay towns, romantic dinners, and water activities.

Firefly - 68' Azimut

  • The Italian-designed and built Firefly turns heads with its sleek lines and lavish leather interiors.
  • With a 6 ft draft, Firefly can access secluded Chesapeake Bay coves and shallow rivers.
  • Features two spacious staterooms, making it an ideal overnight retreat for two couples or accommodating up to 12 guests on a day charter.
  • Suitable for various experiences, from an elegant sunset cruise to a week-long excursion along the Chesapeake Bay, Annapolis, and Baltimore.
  • Firefly ensures your private yacht charter is marked by style, comfort, and luxury.

Photo Gallery

The stunning yacht Muse at her winter home in Miami

Reserve Your Charter Today!

Get in touch.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Send us a message to schedule your charter. We will get back to you soon!

326 1st Street, Suite 403, Annapolis, MD 21403

Mike Esposito / [email protected] 239-227-7879

Copyright © 2024 Elite Charters of Annapolis - All Rights Reserved.

Powered by GoDaddy

This website uses cookies.

We use cookies to analyze website traffic and optimize your website experience. By accepting our use of cookies, your data will be aggregated with all other user data.

Chronic Sailing

Sailing Charters, Lessons & Captain Services in Annapolis, MD & Abroad

We Have a Chronic Sailing Condition

sail with us and you will too!

Annapolis Sailing Charters.

Sail the Chesapeake Bay on your own private yacht. Select a trip from our popular itineraries below, see more sailing trips in the Chesapeake Bay or contact us to customize an itinerary just for you.

sailboat in sunset

Annapolis Sunset Cruise

Catch the gorgeous Chesapeake Bay sunset aboard a luxury catamaran. Perfect for a romantic evening, cocktails with friends or a way to end a day exploring Annapolis.

family hanging out on boat deck

Mid-Week “3 Hour Tour”

“Just sit right back and…” feel the wind in your hair, go for a swim or just enjoy the views. Great for office outings and happy hour hangs.

friends celebrating on a boat

Celebrate Your Special Event

Birthdays, anniversaries, bachelorette parties and other occasions are more fun on your own private yacht! We’ll tailor a cruise for your special day.

sleeping cabin on boat

Chesapeake Overnight Sail

Get away for a night (or 2) and enjoy adventures on the water, excursions into nearby towns, sunset cocktails and sleeping under the stars.

Annapolis Sailing Lessons

ASA certified instructor, Captain Shawn Owen helps students of all skill levels become confident and safe sailors. With decades of experience teaching snowboarding and music, Shawn has a laid back, positive attitude and a passion for sailing and seamanship that will be contagious when you sail with us.

If you’ve never sailed before and are interested in trying it out to see what all the fuss is about, this class may be the perfect way to give it a shot.

Intro to Sailing

Interested in one on one training? Or maybe you want to get you and your crew up to speed before an upcoming charter? We can customize private instruction for up to 4 people for an extremely competitive rate.

Private Sailing Instruction

New boat owner needing insurance checkout or just looking to brush up skills on your own boat? We offer instruction and certifications aboard your boat to maximize benefit and personal knowledge of your vessel.

Learn on your Boat

The American Sailing Association is a national and global leader in sailing education and bareboat chartering certifications. We offer ASA Courses 101-106, as well as the 114 catamaran certification. If bareboat chartering is something you see in your future, then this could be your best avenue to achieve the necessary skills and qualifications required to handle your own charter vessel.

ASA Courses

Learn To Sail

Browse our charter fleet.

Bali 4.4

American Honey

This state-of-the-art catamaran seamlessly combines performance, comfort, and elegance to provide an unforgettable chartering adventure.

This catamaran features expansive deck spaces and an innovative open-concept design, creating a seamless flow between the interior and exterior.

catamaran charter annapolis

Dos Milagros

Experience the ultimate luxury sailing adventure on the stunning Chesapeake Bay aboard the exquisite 2017 Beneteau Oceanis 45, a true gem in the world of yacht chartering.

catamaran charter annapolis

Let us plan your customized “escape” on this well appointed catamaran sailing the Chesapeake Bay out of Annapolis, MD

catamaran charter annapolis

A magnificent vessel that seamlessly blends luxury, performance, and comfort on the open seas.

catamaran charter annapolis

This sleek and modern vessel feature 3 cabins, each equipped with its own private en-suite bathroom. Expansive deck with plenty of seating and lounging areas.

Stay in the Loop

I want to know about new classes, specials, events and offers from Chronic Sailing.

Life is Just Better on a Boat

sail with us!

Sailing changed my life for the better in nearly every way. It makes me more present, more thoughtful, more focused, healthier, happier, just better as a person in most every way. I would be honored to help share it with you and then watch it become a part of your life.

Keep it chronic.

- Captain Shawn

captain shawn with sunset on a boat

Catamaran Charters at Pier 7 Resort Marina!

48 s. river rd. south edgewater, md 21037.

Marina Office: 410.956.2288

It’s no secret that the Chesapeake Bay is home to some of the best sailing destinations in the United States – Annapolis, Maryland is America’s Sailing Capital after all! We’ve put together some great resources and suggested itineraries for your charter experience.

Available boats.

Bali 4.4 3 cabins BVI

Resolute (44ft)

INQUIRE NOW        READ MORE

catamaran charter annapolis

Here are some of the amenities on the property at our charter base, Pier 7 Marina, that you can enjoy before, during or after your charter.

catamaran charter annapolis

THE PIER OYSTER BAR & GRILL RESTAURANT

catamaran charter annapolis

PRIVATE BEACH

Paddle-board & kayak rentals.

Our on-site paddle board and kayak rental is the perfect place for you to rent a couple of boards or even get you and your dog out on a kayak. Whoof on the Wharf is a brand new concept for those who want to create avenues for dogs to be more a part of their humans' lives, and to create opportunities for like-minded dog lovers to socialize. http://www.piersevenmarina.com/sup/ Whoof on the Wharf +1 (667) 777-2275

JET SKI RENTALS:

Let the kids explore the river on a jet ski while you get your provisioning done. https://www.piersevenmarina.com/jetski South River Jet Skis (410) 212-4202

Local Dining & Groceries - all within a few miles of Pier 7 Marina

CVS Pharmacy

Dunkin donuts, giant food grocery store, whole foods market, fresh market, olde solomon's wine & spirits, starbucks coffee, destinations.

Our charter base at Pier 7 is located in Edgewater, MD about a 15-minute drive from Annapolis. Annapolis offers history, incredible beauty, excellent dining, and a proud maritime tradition. One of the oldest and best-preserved towns in North America, our local pubs have been visited by George Washington and other prominent figures of colonial history. The United States Naval Academy is based here - right on the Severn River. Dining options abound, with some restaurants within a 5- minute walk from our docks. From Pier 7 Marina, you are a short sail to Saint Michaels (southeast), Rock Hall (northeast), Annapolis, Galesville and the Rhode River (southwest) for your first night out.

Suggested Charter Routes

White charter:, blue charter:, black charter:.

catamaran charter annapolis

Charter Location Information & Day Sail Options

catamaran charter annapolis

HARNESS CREEK

catamaran charter annapolis

ST. MICHAELS

catamaran charter annapolis

SOLOMONS ISLAND

catamaran charter annapolis

CHESTERTOWN

catamaran charter annapolis

SASSAFRAS RIVER

catamaran charter annapolis

WHITEHALL BAY

Tilghman island.

catamaran charter annapolis

  • CHARTER YACHTS
  • CREWED YACHTS
  • Bareboat Charter
  • Skippered Charters
  • Crewed Yacht Rentals
  • POWERBOAT or MOTORYACHT CRUISING
  • HOUSEBOATING
  • SAILBOAT CHARTERS
  • CATAMARAN CHARTERS
  • SAILING DESTINATIONS & ITINERARIES
  • CHARTER GUIDE

Catamaran Charter Annapolis - Catamaran Rentals

Top-rated yacht charters in annapolis - preselected yacht rentals:.

Catamaran Saona 47 for hire in Port Annapolis Marina

Catamaran Saona 47 for hire in Port Annapolis Marina

  • Saona 47 [Yacht Price incl. Taxes]
  • Barbeque Grill
  • Outboard engine for dinghy
  • Yacht Insurance
  • Final cleaning
  • Damage waiver
  • Cancellation insurance
  • Fuel (for outboarder)
  • Maryland Amusement Tax
  • VAT or sales tax

Cat Elba 45 for rent in Annapolis

Cat Elba 45 for rent in Annapolis

  • Elba 45 [Yacht Price incl. Taxes]

Cat Tanna 47 for hire in Port Annapolis Marina

Cat Tanna 47 for hire in Port Annapolis Marina

  • Tanna 47 [Yacht Price incl. Taxes]
  • Dinghy with engine

Catamaran Isla 40 for hire in Annapolis

Catamaran Isla 40 for hire in Annapolis

  • Isla 40 [Yacht Price incl. Taxes]

Catamaran Astrea 42 for charter in Annapolis

Catamaran Astrea 42 for charter in Annapolis

  • Astrea 42 [Yacht Price incl. Taxes]

Catamaran Aura 51 for rent in Port Annapolis Marina

Catamaran Aura 51 for rent in Port Annapolis Marina

  • Aura 51 [Yacht Price incl. Taxes]

Cat Aura 51 available for charter in Port Annapolis Marina

Cat Aura 51 available for charter in Port Annapolis Marina

Cat Bali 4.4 for rent in Annapolis

Cat Bali 4.4 for rent in Annapolis

  • Bali 4.4 [Yacht Price incl. Taxes]
  • Cockpit cushion
  • Starter Package

Catamaran Lagoon 50 for rent in Port Annapolis Marina

Catamaran Lagoon 50 for rent in Port Annapolis Marina

  • Lagoon 50 [Yacht Price incl. Taxes]
  • Service fee

Cat Elba 45 for hire in Annapolis

Cat Elba 45 for hire in Annapolis

  • Charter tax
  • Virgin Islands Search and Rescue (VISAR)
  • Cruising tax

Catamaran Bali 4.8 for rent in Annapolis

Catamaran Bali 4.8 for rent in Annapolis

  • Bali 4.8 [Yacht Price incl. Taxes]

TOP Yacht Charters - Yacht Rentals

  • Catamaran Charter North Atlantic Ocean
  • Catamaran Charter United States of America
  • Catamaran Charter US Atlantic Coast
  • Catamaran Charter Chesapeake Bay
  • Catamaran Charter Maryland

Catamaran Rental in Annapolis, United States

Book a catamaran in annapolis.

With only a limited number available in the beautiful Annapolis , hiring a catamaran is a fantastic way to spend your next sailing adventure on the eastern American coastline. Book online with Yachtico.com and enjoy the sights of the picturesque Chesapeake Bay and surrounds.

Catamarans are often the first preference for larger groups of sailors, as they are designed for space and comfort. The catamaran has 2 hulls and as a result, a better stability as a result of even weight distribution. In combination with a low lying deck, the catamaran is an ideal option for families with younger children or those who experience seasickness.

Whilst Yachtico endeavours to continue to provide fantastic quality boats and improve the amount of catamarans available in Annapolis, you may also wish to consider hiring a sailing boat in this city or check out other locations in the United states where catamarans are available for hire.

For catamaran rental in Annapolis , check out the great boats we have on offer below and book online today to ensure you get the boat you are seeking in this beautiful destination.

  • YACHT CHARTERS & RENTALS WORLDWIDE
  • Offer your Yacht
  • B2B partner area
  • Terms of use
  • Privacy policy

Payments methods

Using this site requires JavaScript. You are either using a browser that does not support JavaScript or has JavaScript disabled. Please click here for detailed information.

catamaran charter annapolis

Annapolis Yacht Charters

Captain and Bareboat, Cruising or Fishing

Daily through weekly rates

1505 Shipsview Road

Annapolis, MD 21409

[email protected]

410-353-8242

Schooner Woodwind

Sailing Season is Here. Join Us for a Sail!

catamaran charter annapolis

Welcome Aboard!

Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II , for a true sailing experience in Annapolis, Maryland.

Located in the heart of the Chesapeake Bay, Annapolis is “America’s Sailing Capital.” Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay. As a family business, we take great pride in making your sailing experience a memorable one. Our captains and crew are engaging and enthusiastic. Sail away with us!

catamaran charter annapolis

Make your sailing experience a memorable one! Sail away with us!

TripAdvisor

Darling Charters Annapolis

Welcome aboard darling, a classic lobster yacht built on martha’s vineyard.

catamaran charter annapolis

Perfect for those early risers, or for when you have an action packed day and want to fit it all in.

catamaran charter annapolis

Harbor Cruise

catamaran charter annapolis

This cruise will make you feel like a local and discover all that Annapolis has to offer from the water.

catamaran charter annapolis

Sit back and enjoy this cruise around the harbor, and watch as Annapolis lights up with the setting sun.

Wedding on the water photo

Special Event

We are pleased to speak with you to design a unique day on the water.  We think we are the ultimate way to arrive at your special event or wedding , spectator boat for a regatta, or celebrate that special occasion with your friends, family or clients. Contact us to find out how we can bring that added classic elegance to your next event.

A married couple on the darling charters vessel

Blog Posts ‍

What to bring, what to wear , refreshments, cancellation policy, departure & arrival, terms and conditions, the fine print, testimonials.

“The prettiest boat in Annapolis"

"Wonderful captain, conversation, sights, boat & charcuterie board! ‍ I would do it again!

“ l loved being out on the water on a beautiful August afternoon. It was the perfect way to entertain three of my close friends. We enjoyed Champagne, sunshine and a guided tour of Annapolis area creeks and the Chesapeake Bay. We all agreed that our time on the picnic boat was greatly enhanced because of our captain Alexandra"

About the Boat

Darling is a 1973 Wasque 32 (pronounced “Way-squee”) named after Wasque point on Martha’s Vineyard.  She is a much loved classic and one of only 50 built by Martha’s Vineyard Boatworks.     Based on the lobster boat hulls of Maine, she was designed to be a fishing boat for the often challenging waters around the Vineyard and Buzzards Bay. As result she is a seaworthy vessel, cruising smoothly on the near full length keel. Darling had a major refit in the early 2000s that included the hard top and a new engine, and has continued to be upgraded to keep her in great shape. She is a very sea worthy design and also provides a wonderful open cockpit - the perfect setting for your next cruise.

Darling Charters Boat Cruising In Annapolis Maryland

Founded by two lifelong sailors, we wanted to share our love of the water with you and provide the ultimate way to experience Annapolis! ‍ When we found Darling it was love at first sight - book your cruise today to find out why!

Cute Lab Dog Looking Right

miss-anne-banner

Are you looking for an intimate, cozy setting for a cocktail cruise, after-dinner dessert cruise, a marriage proposal or leisurely excursion around the Chesapeake Bay and the Annapolis area?  Miss Anne makes the perfect choice for smaller groups. She is also a fun boat for Bachelor and Bachelorette Parties and she cruises year-round as her main deck can be enclosed in cooler weather.

Her length spans 24’, and Miss Anne calls Annapolis her home port and is only available in Annapolis. Enjoy cruising aboard the Miss Anne with a private charter package for up to 22 people. Light catering is available or you can bring your own food.  Watermark will stock the Miss Anne with beverages of your choice from our selection of beer, wine and canned sodas.

Download our Miss Anne Flyer Here

catamaran charter annapolis

Reserve Miss Anne

 
-->
 
Admiral of the Bay Nautical Event Designers

catamaran charter annapolis

, or large schooners. Your Nautical Event Designers for all your corporate needs, cocktail or dinner cruises, Chesapeake Bay crab feasts, and unique formal dining occassions. We also specialize in nautical engagement, wedding and anniversary parties too! We also accept bitcoins through to enable easy transaction.

COMMENTS

  1. Sailing Yacht Charters

    We provide luxury sailing yacht charters for a few hours, days or weeks in the Chesapeake Bay, Bahamas and Virgin Islands. Skip to content call now (410) 956-9323

  2. Captained and Bareboat Yacht Charter Annapolis MD

    Captained and Bareboat Charters in Annapolis, Maryland. The Chesapeake Bay is among the world's top cruising and sailing destinations. A true American treasure, the Bay delivers a long enjoyable sailing season from early Spring to late Fall, with over 11,000 miles of shoreline to explore. From quiet, unspoiled anchorages, to historic seaside ...

  3. Annapolis Fleet

    Annapolis FAQ. Waypoints Annapolis offers a variety of new model sailing monohulls, catamarans, and powerboats for multi-day charters on the Chesapeake Bay. Our team prides itself in providing an elevated charter experience for each of our guests aboard our meticulously maintained yachts equipped with all of the comforts of home.

  4. Classic Sail Charters

    Your Dream Adventure Awaits. Catering to clients seeking a unique, private sailing adventure for up to six passengers, we offer world-class sailing yachts, decades of experience, and 5-star service to ensure that your charter is truly memorable. All our charters are for private parties, so you can have it your way.is required.

  5. Catamaran Sales

    Sail Away Catamarans is a full-service yacht sales and charter company headquartered just outside of Annapolis, MD, the sailing capital. Our Yacht Brokerage Services include brand new Seawind and Vision catamaran sales, pre-owned yacht sales, yacht management, marketing, charters, sailing instruction and boat services.

  6. Catamaran Rental Annapolis: Charters, MD

    Boat charter prices in Annapolis, MD vary significantly. You can find great budget friendly rentals starting from €250 for a daily trip. Luxury or party yacht rentals for the day can cost up to €6500 where service fees and mandatory extras are not included. Your budget per day will vary depending on whether you are renting the boat in ...

  7. Chesapeake Bay Boat Rentals

    Charter a luxury yacht for a few hours, days or weeks. We provide gorgeous sailing catamaran Chesapeake Bay boat rentals. Charter a luxury yacht for a few hours, days or weeks. ... Historic Downtown Annapolis. Known as America's Sailing Capital, Annapolis has 500 miles of gorgeous shoreline to explore. Annapolis has more surviving 18th century ...

  8. Annapolis Sailing Charters

    Sailing Charters in. Annapolis, MD. Classic Sail Charters offers Chesapeake Bay sailing adventures on our thoroughly refined sailing yacht, the Licentia. It is exquisitely appointed, safe, and ready for you to call home while you enjoy the mystique and allure of some of the best sailing grounds in the world.

  9. Annapolis Catamaran Charters

    ANNAPOLIS CATAMARAN CHARTERS. HOME PORT. More. CATAMARAN EVENT CHARTERS Private day-charter on our catamaran for bachelor/bachelorette parties, birthdays, anniversaries, company functions or any other occasion. Phone (voice and text): 410-941-9463. Email: [email protected]. Report abuse ...

  10. Luxury Catamaran & Yacht Charter in Annapolis

    Luxury Catamaran & Yacht Charter in Annapolis | WS Charters. Book Now. Got questions? Call us at 561-900-6016. Looking for the best day on the Chesapeake Bay? We are fully equipped with full kitchen essentials, a grill, a bathroom, private changing room, a large covered stern table and an outdoor HOT water shower.

  11. Yacht Charter

    This sleek 87 ft sport yacht is available in Annapolis and the Chesapeake Bay. Invite up to 12 guests for half or full-day private yacht charters. She boasts beautiful teak decks, dual salons, and a spacious aft entertainment area. With a 5 ft draft, Muse can navigate secluded coves and anchorages. A 27-knot cruise speed ensures fast travel and ...

  12. Sailing Charters, Lessons & Captain Services in Annapolis, MD & Abroad

    443-333-9113. Book Now. We offer private boat charters, from a few hours to overnight sails, certified sailing instruction and captain services in Annapolis MD and beyond! Sail with us!

  13. The Catamaran Company

    Our charter base at Pier 7 is located in Edgewater, MD about a 15-minute drive from Annapolis. Annapolis offers history, incredible beauty, excellent dining, and a proud maritime tradition. One of the oldest and best-preserved towns in North America, our local pubs have been visited by George Washington and other prominent figures of colonial ...

  14. Seas the Bay

    Experience your own Private Sailing charter on the Chesapeake Bay in Annapolis, Maryland focusing on a family day sails, sunset sails and special event sails. Be on your own sailing yacht for the day or evening with a captain and crew providing gourmet appetizers and delectable meals. Experience the Severn River, Bay and historic Annapolis. Sit ...

  15. Catherine Marie

    Elegant Private Yacht Charters & Rentals in Annapolis, Baltimore, and on the Eastern Shore. Whether you're hosting a large corporate function, a birthday celebration, or an elegant wedding reception, Catherine Marie is one of the grandest yachts available at Yacht Charters on the Bay℠ by Watermark®. Used for private charters in the Annapolis, Baltimore and Eastern Shore area, she has ...

  16. 5 Best Yacht Charters In Annapolis, Maryland

    1. Two-cabin yacht with a fully equipped galley (from USD 299) This 13.11-m (43-ft) Annapolis boat rental is docked in Eastport, only a short walk away from the historic Downtown Annapolis and USNA. It features two private cabins, one with a queen-sized bed and another with bunk beds.

  17. Catamaran Charter Annapolis

    Catamaran Rentals Annapolis › Port Annapolis Marina. Catamaran - Elba 45 - Built in: 2022 - Cabins: 4 - Berths: 8. Bareboat charter. Max 8 persons. The price is calculated for 7 day charter and 1 passenger. Price includes: Elba 45 [Yacht Price incl. Taxes] Outboard engine for dinghy. Yacht Insurance.

  18. Ohana Charters specialize in personalized sailing charters, catamaran

    Midshipmen, share the Annapolis essence with your parents aboard Ohana for a unique Naval Academy Pre-Party/After-Party event! Experience authentic Annapolis living on serene waters, offering breathtaking views and genuine city vibes.

  19. Home

    Annapolis Yacht Charters. Captain and Bareboat, Cruising or Fishing. Daily through weekly rates. 1505 Shipsview Road. Annapolis, MD 21409. [email protected]. 410-353-8242.

  20. Sailing Cruises in Annapolis, Maryland on the Schooner Woodwind on the

    Welcome Aboard! Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II, for a true sailing experience in Annapolis, Maryland. Located in the heart of the Chesapeake Bay, Annapolis is "America's Sailing Capital.". Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the ...

  21. Darling Charters Annapolis

    To an Elevated Yachting Experience on the Historic Annapolis WaterfrontEnjoy fully captained and crewed charters on an elegant picnic yacht. Home; Our Charters; FAQ; Testimonials; Blog; BOOK NOW Call us at 667-225-7184. ... Have a remarkable day on the water with Darling Charters of Annapolis Maryland ...

  22. Miss Anne

    Her length spans 24', and Miss Anne calls Annapolis her home port and is only available in Annapolis. Enjoy cruising aboard the Miss Anne with a private charter package for up to 22 people. Light catering is available or you can bring your own food. Watermark will stock the Miss Anne with beverages of your choice from our selection of beer ...

  23. Annapolis boat charters, Chesapeake Bay boat charters, Baltimore boat

    Admiral of the Bay is your premier nautical event planner; we specialize in Annapolis and Chesapeake Bay boat charters and sail boat charters. Sail boat and power boat charters for weddings, private and corporate parties, event planning on the Chesapeake Bay, Annapolis, Baltimore. Bareboat charters and bareboat rentals in Annapolis and on the Chesapeake Bay.

  24. Madison firefighters trim man's trees after rooftop rescue

    Madison firefighters went the extra mile after rescuing a man from the roof of his garage made a rooftop rescue. Engine 4 was dispatched to a home on West Lawn Avenue just after 8 a.m., where a man had become stranded on the roof of his garage while attempting to trim overhanging tree limbs. The man ...