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All listings in Virginia

Incredible sailboat rentals in Virginia, United States.

5.0(Average of 349 reviews in this area)
View our Virginia sailing boating guide
1 - 24 of 28 listings
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
Sailing in Potomac River · 6 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

5.0
Superowner
Best of 2022
$150hour
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
Sailing in Chesapeake Bay · 6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

5.0
Superowner
$150hour
41' Lagoon Cruising Catamaran in Maryland, United States
Sailing in Potomac River · 12 guests

41' Lagoon Cruising Catamaran in Maryland, United States

5.0
Superowner
Best of 2022
$349hour
"Imi Ola" Seawind 1260
Events in Potomac River · 12 guests

"Imi Ola" Seawind 1260

5.0
Superowner
$716hour
Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
Sailing in Chesapeake Bay · 6 guests

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

5.0
Superowner
$125hour
SpeedBoat | $275 Hr | 10 People
Events in Potomac River · 10 guests

SpeedBoat | $275 Hr | 10 People

New
Superowner
Best of 2022
$275hour
Double Deckers Boat | $450 HR | 14 People
Events in Potomac River · 14 guests

Double Deckers Boat | $450 HR | 14 People

New
Superowner
Best of 2022
$450hour
Let's Go Sail in Gloucester Point, Virginia
Sailing in Chesapeake Bay · 6 guests

Let's Go Sail in Gloucester Point, Virginia

5.0
Superowner
$125hour
Melges 32 - The Ultimate Racing Experience
Sailing in Chesapeake Bay · 8 guests

Melges 32 - The Ultimate Racing Experience

5.0
Superowner
$200hour
Charter this 42ft Sailboat in Edgewater, Maryland for upto 6 persons and sail on beautiful Chesapeake Bay and beat inflation.  Same prices this year as last!!
Sailing in Potomac River · 6 guests

Charter this 42ft Sailboat in Edgewater, Maryland for upto 6 persons and sail on beautiful Chesapeake Bay and beat inflation. Same prices this year as last!!

5.0
$150hour
Beneteau 41ft Sailing Charter in Annapolis, Maryland
Sailing in Potomac River · 8 guests

Beneteau 41ft Sailing Charter in Annapolis, Maryland

5.0
$200hour
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Sailing in Chesapeake Bay · 4 guests

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

4.5
$220night
22' Sea Ray Powerboat for 6 people in Washington, District of Columbia
Powerboats in Potomac River · 6 guests

22' Sea Ray Powerboat for 6 people in Washington, District of Columbia

5.0
$155hour
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Potomac River · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$2,600day
Charters 33' Cape Dory Cruising Monohull In Kilmarnock, Virginia
Sailing in Chesapeake Bay · 4 guests

Charters 33' Cape Dory Cruising Monohull In Kilmarnock, Virginia

5.0
$66hour
Sailing Charter with USCG Licensed Captain
Sailing in Chesapeake Bay · 6 guests

Sailing Charter with USCG Licensed Captain

5.0
$899day
Pearson 26 Coastal Sailboat in Norfolk
Sailing in Chesapeake Bay · 6 guests

Pearson 26 Coastal Sailboat in Norfolk

5.0
$60hour
Brand new Bayliner DX2200 Boat Rental in Baltimore, Maryland
Powerboats in Potomac River · 8 guests

Brand new Bayliner DX2200 Boat Rental in Baltimore, Maryland

5.0
$200hour
Seawind 1260 Cruising Catamaran Rental in Little Harbour, Bahamas
Sailing in Potomac River · 6 guests

Seawind 1260 Cruising Catamaran Rental in Little Harbour, Bahamas

5.0
$1,200day
Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland
Sailing in Chesapeake Bay · 6 guests

Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland

5.0
$349hour
Sunset Champagne Cruise on the Chesapeake Bay
Sailing in Chesapeake Bay · 6 guests

Sunset Champagne Cruise on the Chesapeake Bay

New
$399hour
New Yacht Charter 2022 Bali 5.4 Sailing Catamaran in Severna Park Maryland
Events in Potomac River · 12 guests

New Yacht Charter 2022 Bali 5.4 Sailing Catamaran in Severna Park Maryland

New
$1,100hour
41’ Bristol Sailboat Charter in Solomons Island, MD
Sailing in Potomac River · 6 guests

41’ Bristol Sailboat Charter in Solomons Island, MD

New
$90hour
Sail the Chesapeake Bay, Atlantic Coast or the Caribbean Islands in style! Charter this Jeanneau Sun Odyssey 509
Sailing in Chesapeake Bay · 8 guests

Sail the Chesapeake Bay, Atlantic Coast or the Caribbean Islands in style! Charter this Jeanneau Sun Odyssey 509

New
$1,240day

Sailing Reviews in Virginia

  1. Gina
    Gina
    41' Lagoon Cruising Catamaran in Maryland, United States

    Captain Jess, the catamaran, the outing, the sights, all of it EXCEEDED our group’s expectations (which were already high going in)!! We immediately felt comfortable and secure in Captain Jess upon initial meeting (especially because he quickly outlined safety rules first - green flag!) and the hours out on the water became the highlight of my sister’s bachelorette weekend - we will be forever grateful!

  2. IM
    Ivan
    Beneteau 41ft Sailing Charter in Annapolis, Maryland

    Gus is a great host and his boat is large and well maintained. He is clearly an experienced skipper who has an intimate knowledge of the waters around Annapolis and the bay. Very relaxing cruise

  3. AW
    Alan
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Perfect for a few hours or the whole day. The captain made it easy as he knew all the trick of the area so we just needed to sit back and enjoy or man the helm to steer Down wind is the perfect time for light fair and another beverage. We will keep Capt Albert on our short list if we want to get away for an after noon Thanks Alberto

  4. VF
    Vanessa
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    We loved our day with Alberto and Grace! A great boat, and such a fun outing on the water. Even with lighter wind today, we had an amazing time. Alberto was helpful and responsive in our initial communications and planning. We would absolutely head back out with Captain Alberto again. Thank you!

  5. MC
    Matthew
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Capt. Alberto and his wife were super hosts for us today. We had a wonderful time, it was easy to get to and on the boat, got to pull some lines and steer the boat. Good stories and sailing pointers as well! It was a beautiful day with the right amount of sun and wind! Best way to celebrate my 40th Birthday! thanks so much Capt!

  6. Michelle
    Michelle
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Loved everything about this experience, and it blew our group’s expectations out of the water! It was a big enough boat for 6 of us, and we had drinks and snacks brought onboard. Alberto and his wife were very accommodating when we wanted to go swimming and allowed one of us to man the ship (with tips and supervision of course). Would definitely book again!

Boating Guide - Virginia Sailing

Rent or charter a sailboat for a memorable experience in Virginia.

Are you ready for a fun adventure out on the open water onboard a sailboat in Virginia? Rent or charter a sailboat with or without a captain and experience the joy of exploring the water by wind power. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime. Virginia is a wonderful sailboat rental destination.

Using GetMyBoat to book your next sailing experience.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

GetMyBoat has 28 listings for Sailing experiences in Virginia with 349 reviews.

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