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    All listings in Virginia

    Incredible sailboat rentals in Virginia, United States.

    5.0
    (399 Reviews)

    Page 2 of 2 • 39 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD
    Sailing in Rock Hall · 4 guests

    Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

    5.0
    $150/hour
    Experience the Charm of St. Michaels Aboard the 41ft Sail Selina 2hr Boat Tour
    Sailing in Saint Michaels · 6 guests

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

    New
    $350/hour
    Fish On! Rent Your 38ft Dawson Sportfish in Norfolk, VA
    Sailing in Norfolk · 6 guests

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

    New
    $725/day
    STARZ -Lagoon 42 Catamaran in Chesapeake Bay
    Sailing in Annapolis · 13 guests

    STARZ -Lagoon 42 Catamaran in Chesapeake Bay

    New
    $400+/hour
    Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape
    Sailing in Annapolis · 13 guests

    Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape

    New
    $350+/hour
    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
    Sail the Sea on the Pintita
    Sailing in Annapolis · 20 guests

    Sail the Sea on the Pintita

    New
    $500+/hour
    DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!
    Sailing in Annapolis · 10 guests

    DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!

    New
    $232+/hour
    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
    VIKO 30 Premium Sailing Yacht In Deale, MD
    Sailing in Deale · 5 guests

    VIKO 30 Premium Sailing Yacht In Deale, MD

    New
    $925/day
    New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
    Sailing in Annapolis · 13 guests

    New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

    New
    $1,100/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
    34ft Sailing Yacht in Annapolis, Maryland
    Sailing in Annapolis · 4 guests

    34ft Sailing Yacht in Annapolis, Maryland

    New
    $250/hour

    Top Destinations Nearby

    Sailing Reviews in Virginia

    1. MP

      Mohan

      Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

      Captain Rob made the trip memorable with the beautiful views of the Chesapeake sunset and anecdotes of the area and his marine career.

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