Overnight: $350
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.
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.
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.
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!
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.
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.
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.
Come join us for an unforgettable cruise on one of our world-class sailing yachts and enjoy the beautiful sunsets in Chesapeake bay!
Classic Sail Charters offers Chesapeake Bay sailing adventures on a thoroughly refined sailing yacht Licentia, a 2008 Catalina 42 MKII.
Come sail with us on the Chesapeake Bay! As the largest estuary in the world, the Chesapeake Bay is stunningly beautiful!
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.
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 EVENT CHARTERS
Private day-charter on our catamaran for bachelor/bachelorette parties, birthdays, anniversaries, company functions or any other occasion.
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
Luxury yacht charter experiences.
Unique and Unforgettable Memories Await in Annapolis and on the Chesapeake Bay
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.
The stunning yacht Muse at her winter home in Miami
Get in touch.
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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.
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We Have a Chronic Sailing Condition
sail with us and you will too!
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.
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.
“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.
Birthdays, anniversaries, bachelorette parties and other occasions are more fun on your own private yacht! We’ll tailor a cruise for your special day.
Get away for a night (or 2) and enjoy adventures on the water, excursions into nearby towns, sunset cocktails and sleeping under the stars.
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
Browse our charter fleet.
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.
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.
Let us plan your customized “escape” on this well appointed catamaran sailing the Chesapeake Bay out of Annapolis, MD
A magnificent vessel that seamlessly blends luxury, performance, and comfort on the open seas.
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.
I want to know about new classes, specials, events and offers from Chronic Sailing.
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
48 s. river rd. south edgewater, md 21037.
Marina Office: 410.956.2288
Available boats.
INQUIRE NOW READ MORE
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.
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
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
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.
White charter:, blue charter:, black charter:.
Tilghman island.
Top-rated yacht charters in annapolis - preselected yacht rentals:.
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.
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Annapolis Yacht Charters
Captain and Bareboat, Cruising or Fishing
Daily through weekly rates
1505 Shipsview Road
Annapolis, MD 21409
410-353-8242
Sailing Season is Here. Join Us for a Sail!
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!
Welcome aboard darling, a classic lobster yacht built on martha’s vineyard.
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.
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"
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.
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!
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
Reserve Miss Anne
Admiral of the Bay Nautical Event Designers |
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, 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
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
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 ...
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.
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.
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.
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 ...
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 ...
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.
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 ...
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.
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 ...
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!
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 ...
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 ...
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 ...
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.
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.
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.
Annapolis Yacht Charters. Captain and Bareboat, Cruising or Fishing. Daily through weekly rates. 1505 Shipsview Road. Annapolis, MD 21409. [email protected]. 410-353-8242.
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 ...
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 ...
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 ...
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.
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 ...