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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
$210-$930
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$150-$400
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$65-$600
Fishing Charters
Let a captain do the driving while you do the fishing
$65-$600
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$65-$600
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$195
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$105-$150
Kayaks
Who says you need a motor to have fun on the water?
$65
Top Sailboat Rental Locations Near Annapolis
Recent Reviews in Annapolis
Marie
38-ft Hunter 376 Sailing Adventure in Annapolis
We thoroughly enjoyed our time with Alberto and his wife, Grace. Alberto is a delight to sail with - we learned so much from him. Grace is so lovely and gracious. We sailed around Annapolis during Memorial Day weekend and the weather was perfect. Alberto was very accommodating and friendly. We hope to see you again soon!
Sam
38-ft Hunter 376 Sailing Adventure in Annapolis
Captain Alberto is a wonderful Captain. Handles the boat with an expert confidence and was also a willing and kind teacher to my two kids who had millions of questions.
MR
Matt
STARZ -Lagoon 42 Catamaran in Chesapeake Bay
Great experience and our family and friends had a wonderful time. Clean boat and fun crew to help us celebrate a special occasion. Highly recommend!
hg
hunter
Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.
we did our engagement pictures on the boat & everything was great! Bill was super cooperative & made sure we got all of the best spots for pictures! highly recommend!
DD
Danuta
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
What an enjoyable experience! Captain Joe was always attuned to our wishes, making an extra effort to make this afternoon pleasant for all. His company is very agreeable. We wish we could relive yesterday's feeling of complete relaxation over and over!
DeWitt
38-ft Hunter 376 Sailing Adventure in Annapolis
We had a great afternoon with wonderful hosts. They were great company, so friendly and went out of their way to help make a terrific time.
Top Sailboat Rental Locations in the United States
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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