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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
$170-$810
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$75-$295
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$95-$545
Fishing Charters
Let a captain do the driving while you do the fishing
$75-$740
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$80-$765
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$45-$435
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$220-$1,300
Kayaks
Who says you need a motor to have fun on the water?
$80-$200
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
110 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!
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!
Elisabeth
Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
Charles & Renee were amazing! We booked last minute and enjoyed an awesome afternoon on The Optimystic in Chesapeake Bay!! We can’t wait to sail again!! Charles is an excellent Captain and host. A good teacher as well! Have an awesome winter!! See you in the Spring!! Charlie, Beth and Sam (Class of 2026) ⚓️⚓️⚓️
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.
DL
Dylan
Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
Had the best time. Great boat and experience. Communication,knowledge, and time was phenomenal. A+
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!
Top Sailboat Rental Locations in the United States
Los Angeles, California
376 boats to rent
San Francisco, California
74 boats to rent
Miami, Florida
922 boats to rent
Marina del Rey, California
136 boats to rent
Honolulu, Hawaii
58 boats to rent
Oakland, California
42 boats to rent
New York, New York
87 boats to rent
Annapolis, Maryland
49 boats to rent
San Diego, California
99 boats to rent
Newport Beach, California
134 boats to rent
Charleston, South Carolina
119 boats to rent
Chicago, Illinois
280 boats to rent
Baltimore, Maryland
44 boats to rent
Riviera Beach, Florida
122 boats to rent
West Palm Beach, Florida
83 boats to rent
Palm Beach, Florida
127 boats to rent
Southampton, New York
65 boats to rent
Hitchcock, Texas
55 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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