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The Best Sailboat Rentals in Annapolis
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Annapolis
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$235-$825
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$235-$385
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$350-$465
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$195-$255
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$115-$460
Fishing Charters
Let a captain do the driving while you do the fishing
$115-$460
Top Sailboat Rental Locations Near Annapolis
Baltimore, Maryland
44 boats to rent
Washington, District of Columbia
111 boats to rent
Arlington, Virginia
28 boats to rent
Fort Washington, Maryland
7 boats to rent
Potomac River, United States
176 boats to rent
Cape May, New Jersey
8 boats to rent
Wildwood, New Jersey
8 boats to rent
Lake Anna, Virginia
10 boats to rent
Chesapeake Bay, United States
219 boats to rent
Richmond, Virginia
15 boats to rent
Toms River, New Jersey
18 boats to rent
Brick, New Jersey
12 boats to rent
Norfolk, Virginia
8 boats to rent
Virginia Beach, Virginia
19 boats to rent
Brielle, New Jersey
18 boats to rent
Chesapeake, Virginia
29 boats to rent
Belmar, New Jersey
11 boats to rent
Keyport, New Jersey
11 boats to rent
Recent Reviews in Annapolis
ML
Martha
50ft Catamaran Charter with Water Toys - Annapolis, MD
We intentionally booked a late afternoon cruise around the Chesapeake so we would return around sunset to get great views and photos. Kristal was super responsive in preparing us and Captain Wayne and his 'first mate' Mish were super helpful with capturing the perfect photos. We would definitely book again!
CR
Chawin
38-ft Hunter 376 Sailing Adventure in Annapolis
Captain Alberto and Grace are wonderful hosts and guides. They have a wealth of sailing and life experience to share during your trip. They were very flexible with us during a proposal event.
AP
Andrea
38-ft Hunter 376 Sailing Adventure in Annapolis
This was our crew’s second trip with Capt Alberto and was a second great experience. Capt Alberto shares his passion for sailing and teaching sailing! Capt and Grace are incredibly kind and make a great day spent out on the bay!
Kasie
38-ft Hunter 376 Sailing Adventure in Annapolis
Wonderful Captain and wonderful boat! Plenty of shade above and below deck if the August heat becomes too much. We did the three hour tour, and it was a great half day length. We received a tour of downtown Annapolis and then Captain Alberto opened up the sails and we went on a beautiful ride down the river. It was fun and unique - even for those who have motor boat experience. Sailing is quintessential Annapolis and Captain Alberto was a great host.
Bobby
38-ft Hunter 376 Sailing Adventure in Annapolis
We went out for an afternoon sail with Capt Alberto and had an amazing time. We were blessed with a beautiful sunny day with perfect wind. Capt Alberto shared interesting stories and taught us a good bit about sailing along the way. Highly recommend!
LP
Laura
38-ft Hunter 376 Sailing Adventure in Annapolis
Captain Alberto and his wife are absolute jewels! We sailed with them a couple of years ago and were excited to have this time with them today. They are friendly, professional and just such a joy to be around. Will be seeing them again soon, for sure!
Top Sailboat Rental Locations in the United States
Los Angeles, California
374 boats to rent
Miami, Florida
947 boats to rent
San Francisco, California
74 boats to rent
Marina del Rey, California
136 boats to rent
Honolulu, Hawaii
56 boats to rent
Oakland, California
42 boats to rent
New York, New York
86 boats to rent
San Diego, California
102 boats to rent
Charleston, South Carolina
121 boats to rent
Newport Beach, California
133 boats to rent
Baltimore, Maryland
44 boats to rent
Chicago, Illinois
282 boats to rent
Hitchcock, Texas
56 boats to rent
Texas City, Texas
38 boats to rent
Dania Beach, Florida
258 boats to rent
Long Beach, California
82 boats to rent
Noyack, New York
46 boats to rent
Southampton, New York
65 boats to rent
How To Book on Getmyboat
Browse
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Inquire & Book
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Enjoy
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
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