Book a sailboat rental in Annapolis and sail the Chesapeake Bay

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Boats with this tag offer updated booking conditions in the context of coronavirus, making it easier for you to plan your holiday.
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Sail Annapolis and rekindle your passion for sailing

A private sailboat charter in Annapolis is a unique experience, particularly from late April up to the end of the summer. If you rent a sailboat in Annapolis you can take part in the famous Wednesday Night Races, where more than hundred yachts compete for a big prize. Or take it easy by sailing at your own leisure in Annapolis and perhaps continuing to sail to quaint waterfront towns like Rock Hall, Chestertown, Chesapeake City, and St. Michaels. You will be sure to enjoy everything these little communities have to offer, from history, culture, and food- be sure to eat some crab, a specialty of the Chesapeake Bay.


Opt for a sailboat charter in Annapolis

On Click&Boat you can pick from a wide range of vessels if you are planning to sail in Annapolis. Catamarans and sailboats are perfect to sail the waters of the Chesapeake Bay and Atlantic Ocean. With a sailboat you can take advantage of the local winds and set on an unforgettable tour of the Bay, exploring the charming waterfront towns, marinas and beaches. And don't forget, you can charter a sailboat in Annapolis with or without a skipper, depending on your sailing experience and qualifications.


  • Sailboat
  • Motorboat
  • Catamaran
  • RIB
  • Jet ski
  • Houseboat
  • Yacht
Price
0 - 1000+ € /day
  • Discounts
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Length
0 - 60 m
Engine
0 - 250 hp
Year
2000 - 2021
Manufacturer
Radius
100 km max.
Harbour
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Annapolis is the epicenter of America's boating culture, boasting a long tradition as a sailing hub. If you rent a sailboat in Annapolis, you might have a chance to visit the U.S. Naval Academy, which has served as the U.S. Navy's most prestigious academic institution since 1845. Other attractions include the Ego Alley, a narrow waterway in downtown Annapolis that every respectable boatman has navigated at least once. Of course, by far, the biggest sailing attraction in Annapolis is the U.S. Sailboat Show, attracting boating aficionados from all over the world every October. It's probably the most prestigious and oldest sailboat show. Boating lovers who charter a yacht in Annapolis during the show can tour the Annapolis Dock and have a glimpse of some of the world's most stunning- or in some cases peculiar - sailboats in the world.

Charter a sailboat near Annapolis

In Annapolis, 45 privately owned sailboat are available for charter. See other yachts in the area

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