Cookies!
We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.
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
$160-$865
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$95-$590
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$75-$295
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
50 boats to rent
Arlington, Virginia
28 boats to rent
Virginia Beach, Virginia
20 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
8 boats to rent
Recent Reviews in Virginia
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.
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!
ES
Emil
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
Capt. Joe gave us a wonderful afternoon! He is friendly, knowledgable, and fun! The boat is perfect for cruising around the Bay. Lots of space to lay out and clean facilities downstairs. An excellent value!
Top Sailboat Rental Locations in the United States
Los Angeles, California
369 boats to rent
Marina del Rey, California
135 boats to rent
Miami, Florida
905 boats to rent
San Francisco, California
69 boats to rent
Honolulu, Hawaii
58 boats to rent
New York, New York
90 boats to rent
Oakland, California
39 boats to rent
Annapolis, Maryland
50 boats to rent
San Diego, California
98 boats to rent
Newport Beach, California
131 boats to rent
Baltimore, Maryland
44 boats to rent
Charleston, South Carolina
117 boats to rent
Chicago, Illinois
281 boats to rent
Dania Beach, Florida
238 boats to rent
Southampton, New York
72 boats to rent
Hitchcock, Texas
54 boats to rent
Noyack, New York
46 boats to rent
Houston, Texas
45 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!
Dive into Our Journal
April 17, 2024
Boating Regulations in Virginia Beach, VA
Read Article
December 30, 2019
Smith Mountain Lake Boating Guide - Getmyboat
Read Article
December 19, 2019
Virginia Beach Boating Guide - Getmyboat
Read Article
August 01, 2023
10 Boating Adventures of a Lifetime
Read Article
October 03, 2022
Getmyboat's Guides to the World of Boating
Read Article
August 12, 2021
Caribbean Flavors on the Water in NYC - Book an Anchored & Chef'd Catered Cruise with Getmyboat!
Read Article
Real reviews from happy Getmyboaters.
4.9 out of 5! 500,000+ reviews
