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The Best Sailboat Rentals in Virginia
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Virginia
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$175-$800
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$105-$495
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$80-$310
Fishing Charters
Let a captain do the driving while you do the fishing
$80-$700
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$80-$715
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$45-$365
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$225-$985
Kayaks
Who says you need a motor to have fun on the water?
$85-$195
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$150-$165
Rafting
A high-energy adventure for the whole family
$130
Top Sailboat Rental Locations Near Virginia
Washington, District of Columbia
111 boats to rent
Annapolis, Maryland
49 boats to rent
Arlington, Virginia
28 boats to rent
Virginia Beach, Virginia
19 boats to rent
Richmond, Virginia
15 boats to rent
Lake Anna, Virginia
10 boats to rent
Norfolk, Virginia
8 boats to rent
Fort Washington, Maryland
7 boats to rent
Recent Reviews in Virginia
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.
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!
Jordan
50ft Catamaran Charter with Water Toys - Annapolis, MD
Captain Deren and the crew were amazing — they made my birthday so special. They were super accommodating the entire day for everyone! They were even kind enough to put up some birthday decorations for our group. I’m definitely going to be booking with Captain Deren again!
Top Sailboat Rental Locations in the United States
Los Angeles, California
376 boats to rent
Miami, Florida
949 boats to rent
San Francisco, California
77 boats to rent
Marina del Rey, California
137 boats to rent
Oakland, California
43 boats to rent
Honolulu, Hawaii
52 boats to rent
New York, New York
86 boats to rent
Annapolis, Maryland
49 boats to rent
San Diego, California
101 boats to rent
Charleston, South Carolina
122 boats to rent
Newport Beach, California
133 boats to rent
Long Beach, California
84 boats to rent
Baltimore, Maryland
44 boats to rent
Chicago, Illinois
281 boats to rent
Hitchcock, Texas
56 boats to rent
Texas City, Texas
38 boats to rent
Dania Beach, Florida
258 boats to rent
Palm Beach, Florida
143 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!
Real reviews from happy Getmyboaters.
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