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All listings in Virginia

Incredible sailboat rentals in Virginia, United States.

Page 2 of 233 listings

Sail on the Potomac in Washington, DC aboard the 28ft Hunter Sailboat
Sailing in Washington · 6 guests

Sail on the Potomac in Washington, DC aboard the 28ft Hunter Sailboat

New
$280/hour
Instant Book
Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours
Sailing in Saint Michaels · 6 guests

Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours

New
$400/hour
Sail the Chesapeake Bay, Atlantic Coast or the Caribbean Islands in style! Charter this Jeanneau Sun Odyssey 509
Sailing in Deltaville · 8 guests

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

New
$524+/day
 VIKO S 35 Sailboat in Deale
Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New
$298/hour
41’ Bristol Sailboat Charter in Solomons Island, MD
Sailing in Solomons · 6 guests

41’ Bristol Sailboat Charter in Solomons Island, MD

New
$90/hour
VIKO 30 Premium Sailing Yacht In Deale, MD
Sailing in Deale · 5 guests

VIKO 30 Premium Sailing Yacht In Deale, MD

New
$925/day
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250/hour
50ft Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

5.0
Snoozed - Active 08 Jul 2025
STARZ -Lagoon 42 Catamaran in Chesapeake Bay
Sailing in Annapolis · 13 guests

STARZ -Lagoon 42 Catamaran in Chesapeake Bay

5.0
Snoozed - Active 02 Oct 2025

Sailing Reviews in Virginia

  1. MR

    Matt

    STARZ -Lagoon 42 Catamaran in Chesapeake Bay

    Great experience and our family and friends had a wonderful time. Clean boat and fun crew to help us celebrate a special occasion. Highly recommend!

  2. Jordan

    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!

  3. DW

    Dominique

    50ft Catamaran Charter with Water Toys - Annapolis, MD

    Amazing experience! Amazing, professional crew! It was very easy to book from the beginning. We had an amazing time! Group of 12.

  4. JM

    Josephine

    50ft Catamaran Charter with Water Toys - Annapolis, MD

    I will charter the boat over, and over again because of their warm hospitality. I will recommend them to everyone

  5. Angela

    Angela

    50ft Catamaran Charter with Water Toys - Annapolis, MD

    Amazing! Fun! Professional, Great value for the money paid. One of the best ever! Coming back soon.

  6. EM

    Esha

    50ft Catamaran Charter with Water Toys - Annapolis, MD

    The boat was fabulous, the crew was so attentive, and my family and friends had an amazing time.