Cookies & Agreements
By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.
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-$800
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$80-$315
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$100-$495
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$80-$715
Fishing Charters
Let a captain do the driving while you do the fishing
$80-$710
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
$220-$1,110
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
110 boats to rent
Annapolis, Maryland
43 boats to rent
Arlington, Virginia
27 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
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!
DD
Danuta
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
What an enjoyable experience! Captain Joe was always attuned to our wishes, making an extra effort to make this afternoon pleasant for all. His company is very agreeable. We wish we could relive yesterday's feeling of complete relaxation over and over!
George
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
HIGHLY recommend Capt Joe for a fantastic sailing experience out of Rock Hall. Joe worked with us to get a last-minute booking when another booking fell through. He and his crew are experts and you will not be disappointed. He let us take the helm and participate as much or as little as we wanted to. Sol Searcher is a beautiful, well-equipped boat - plenty of comfort and speed (wind dependent of course.)
LR
Loretta
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
What a gorgeous day on the water aboard Sol Searcher! Captain Joe was an awesome host for our day! Peaceful, serene and exactly what we were hoping for to bring the summer to a close. What a lovely world we have to enjoy when we step away from the hustle of life and take the opportunity to take in all that it has to offer. Thank you Capt’n Joe for a wonderful sailing experience. Until we meet again, Loretta and Greg
Top Sailboat Rental Locations in the United States
Los Angeles, California
396 boats to rent
Miami, Florida
979 boats to rent
San Francisco, California
72 boats to rent
Marina del Rey, California
144 boats to rent
Honolulu, Hawaii
51 boats to rent
Oakland, California
43 boats to rent
New York, New York
86 boats to rent
San Diego, California
100 boats to rent
Hitchcock, Texas
62 boats to rent
Texas City, Texas
43 boats to rent
Charleston, South Carolina
122 boats to rent
Miami Beach, Florida
394 boats to rent
Houston, Texas
49 boats to rent
Kemah, Texas
40 boats to rent
Clear Lake Shores, Texas
37 boats to rent
Chicago, Illinois
280 boats to rent
Long Beach, California
91 boats to rent
Annapolis, Maryland
43 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
