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All listings in Virginia

Incredible sailboat rentals in Virginia, United States.

5.0

(417 Reviews)

Page 1 of 2 • 33 listings

Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0

Superowner

$100+/hour

Instant Book

Events in Washington · 13 guests

SEARAY SLX400 | $800hr | 13 People

5.0

Superowner

Best of 2025

$800/hour

Instant Book

Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

5.0

$425/hour

Sailing in Rock Hall · 6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

5.0

$150/hour

Sailing in Gloucester Point · 6 guests

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

5.0

Superowner

$125/hour

Powerboats in Fort Washington · 6 guests

2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River

5.0

$150+/hour

Sailing in Mayo · 6 guests

Take your Sailing Dream on Chesapeake Bay. Rates reduced to for that dream!!

5.0

$150+/hour

Sailing in Gloucester Point · 6 guests

Let's Go Sail in Gloucester Point, Virginia

5.0

Superowner

$117+/hour

Sailing in Kilmarnock · 4 guests

Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia

5.0

$15+/hour

Sailing in Rock Hall · 4 guests

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

4.6

$275+/night

Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0

$250+/hour

Sailing in Annapolis · 12 guests

SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

5.0

$400+/hour

Sailing in Annapolis · 13 guests

STARZ -Lagoon 42 Catamaran in Chesapeake Bay

5.0

$400+/hour

Sailing in Essex · 6 guests

Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese

5.0

$150/hour

Sailing in Hampton · 5 guests

Melges 24 - One Design Racing Experience

5.0

Superowner

$100/hour

Powerboats in Washington · 6 guests

Come Experience the ambient waters of the Potomac on the Sylvan MIRAGE Pontoon!

5.0

$185/hour

Sailing in Annapolis · 13 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

5.0

$1,100/hour

Sailing in Edgewater · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0

$425/hour

Sailing in Saint Michaels · 6 guests

Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail

5.0

$325/hour

Sailing in Rock Hall · 6 guests

43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

5.0

$150+/hour

Sailing in Annapolis · 12 guests

SLOWDOWN - DUFOUR 430

New

$250+/hour

Sailing in Saint Michaels · 6 guests

Experience the Charm of St. Michaels Aboard the 41ft Sail Selina 2hr Boat Tour

New

$350/hour

Sailing in Norfolk · 6 guests

Fish On! Rent Your 38ft Dawson Sportfish in Norfolk, VA

New

$725/day

Sailing in Annapolis · 10 guests

DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!

New

$232+/hour

Top Destinations Nearby

Sailing 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!