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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
$205-$920
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$350-$480
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$230-$400
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$195-$260
Fishing Charters
Let a captain do the driving while you do the fishing
$95-$480
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$95-$480
Top Sailboat Rental Locations Near Annapolis
Baltimore, Maryland
44 boats to rent
Washington, District of Columbia
110 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
20 boats to rent
Brielle, New Jersey
18 boats to rent
Chesapeake, Virginia
30 boats to rent
Belmar, New Jersey
11 boats to rent
Keyport, New Jersey
11 boats to rent
Recent Reviews in Annapolis
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!
Lisa
38-ft Hunter 376 Sailing Adventure in Annapolis
Thank you so much Captain Alberto & Grace. We had a fabulous time and enjoyed learning about sailing. Thanks for trusting us to help steer and tack the boat. We had so much fun. You are a great teacher. We wish we could have stayed out longer.
JS
Jen
STARZ -Lagoon 42 Catamaran in Chesapeake Bay
I highly recommend Chronic Sailing! We did a 4 hour charter out of Annapolis as a bachelorette party. Captain Steve and Sarah were so accommodating and made our time so memorable. We are so appreciative. They made everything so easy- from booking to sailing and making memories with us. The STARZ catamaran boat was incredible! It fit our big group comfortably and gave us a little bit of luxury as we lounged and enjoyed on the bay. Again, this was a great experience for all of us and I would love to use them again!
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.
GJ
G Aaron
38-ft Hunter 376 Sailing Adventure in Annapolis
Alberto and his wife are an amazing and wonderful couple who truly made our experience magical.
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!
Top Sailboat Rental Locations in the United States
Los Angeles, California
377 boats to rent
San Francisco, California
74 boats to rent
Marina del Rey, California
137 boats to rent
Miami, Florida
915 boats to rent
Honolulu, Hawaii
58 boats to rent
Oakland, California
42 boats to rent
New York, New York
90 boats to rent
San Diego, California
101 boats to rent
Newport Beach, California
133 boats to rent
Charleston, South Carolina
119 boats to rent
Chicago, Illinois
281 boats to rent
Baltimore, Maryland
44 boats to rent
Dania Beach, Florida
247 boats to rent
Southampton, New York
67 boats to rent
Hitchcock, Texas
55 boats to rent
Noyack, New York
46 boats to rent
Texas City, Texas
37 boats to rent
Tampa, Florida
426 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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