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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
$220-$995
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$125-$660
Fishing Charters
Let a captain do the driving while you do the fishing
$85-$530
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$85-$530
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$180-$260
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$155-$205
Top Sailboat Rental Locations Near Annapolis
Selby-on-the-Bay, Maryland
7 boats to rent
Baltimore, Maryland
51 boats to rent
Oxon Hill, Maryland
8 boats to rent
Washington, District of Columbia
120 boats to rent
Arlington, Virginia
31 boats to rent
Fort Washington, Maryland
14 boats to rent
Potomac River, United States
165 boats to rent
Cape May, New Jersey
9 boats to rent
Wildwood, New Jersey
9 boats to rent
Lake Anna, Virginia
8 boats to rent
Chesapeake Bay, United States
209 boats to rent
Richmond, Virginia
7 boats to rent
Long Beach Island, New Jersey
8 boats to rent
Toms River, New Jersey
18 boats to rent
Brick, New Jersey
12 boats to rent
Virginia Beach, Virginia
17 boats to rent
Brielle, New Jersey
18 boats to rent
Chesapeake, Virginia
28 boats to rent
Recent Reviews in Annapolis
RM
Richard
38-ft Hunter 376 Sailing Adventure in Annapolis
Capt. Alberto and his wife were awesome hosts! They were totally flexible about our schedule and it was great to hear about his prior sailing experiences. It was great to be with such an experienced host! We will definitely book with them in the future!!
MK
Michael
38-ft Hunter 376 Sailing Adventure in Annapolis
Capt Alberto is great. Very knowledgeable and very pleasant. He lets you participate in manning the boat as much as you want and is especially good and introducing new sailors to the glorious activity. Highly recommend!
MB
Maya
38-ft Hunter 376 Sailing Adventure in Annapolis
Capt Alberto and his wife were SO AMAZING!! They taught us how to sail and we sailed across the Chesapeake. Their boat is beautiful and their company is great. I highly recommend everyone book if they are looking to sail in the Annapolis area for a few hours, learn about sailing, and have a relaxing time.
Cindy
38-ft Hunter 376 Sailing Adventure in Annapolis
We had a wonderful time on the water with Captain Alberto and Grace! Their wealth of sailing knowledge of the bay and beyond was quite entertaining and impressive. Thanks for sharing your lovely boat with us.
CK
Christine Mahoney
38-ft Hunter 376 Sailing Adventure in Annapolis
Capt. Alberto was wonderful, his boat beautiful and we had the most glorious morning on the water. It was seamless, efficient, lovely and our whole family said it was the highlight of there vacation and week.
Geoffrey
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Icarus is a great boat and very well equipped. The sails and everything else on the vessel are in great shape and the fact it only draws 4' 6" is perfect for the Chesapeake. I spent a week on Icarus and everything worked well. The value of chartering Icarus is undeniable. I plan to charter Icarus again. Icarus has a lot of sail area, so if the winds are strong douse the headsail early.
Top Sailboat Rental Locations in the United States
Los Angeles, California
358 boats to rent
San Francisco, California
82 boats to rent
Oakland, California
47 boats to rent
Marina del Rey, California
124 boats to rent
Honolulu, Hawaii
42 boats to rent
Miami, Florida
770 boats to rent
San Diego, California
106 boats to rent
New York, New York
82 boats to rent
Chicago, Illinois
288 boats to rent
Kemah, Texas
44 boats to rent
Charleston, South Carolina
127 boats to rent
Hitchcock, Texas
52 boats to rent
Texas City, Texas
42 boats to rent
Houston, Texas
52 boats to rent
Clear Lake Shores, Texas
40 boats to rent
Baltimore, Maryland
51 boats to rent
Tampa, Florida
383 boats to rent
Saint Petersburg, Florida
254 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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