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Getmyboat Logo
    05/03/2024  ± 2 days
    All listings in Virginia

    Incredible sailboat rentals in Virginia, United States.

    5.0
    (422 Reviews)

    Page 1 of 2 • 32 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River
    Powerboats in Fort Washington · 6 guests

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

    5.0
    $150-$190hour
    Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️
    Events in Baltimore · 12 guests

    Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️

    5.0
    Superowner
    Best of 2023
    $389-$459hour
    41' Lagoon Catamaran in Maryland
    Sailing in Annapolis · 12 guests

    41' Lagoon Catamaran in Maryland

    5.0
    Superowner
    Best of 2023
    $390hour
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland
    Sailing in Annapolis · 6 guests

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    5.0
    Superowner
    Best of 2023
    $138-$150hour
    Chesapeake Bay Sailing Charter - 33' Cape Dory sailing from Kilmarnock, Virginia
    Sailing in Kilmarnock · 6 guests

    Chesapeake Bay Sailing Charter - 33' Cape Dory sailing from Kilmarnock, Virginia

    5.0
    $73-$112hour
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
    Sailing in Rock Hall · 6 guests

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    5.0
    Superowner
    $150hour
    Experience the Serenity of Sailing SV Magic
    Sailing in Mayo · 6 guests

    Experience the Serenity of Sailing SV Magic

    4.8
    $165hour
    50ft Catamaran Charter with Water Toys - Annapolis, MD
    Sailing in Annapolis · 12 guests

    50ft Catamaran Charter with Water Toys - Annapolis, MD

    New
    $450hour
    The Licensed Captain of this 42ft Sailboat, provides charters on Chesapeake Bay.
    Sailing in Mayo · 6 guests

    The Licensed Captain of this 42ft Sailboat, provides charters on Chesapeake Bay.

    5.0
    $175hour
    30 ft sailboat with highly experienced Captain in Baltimore Inner Harbor
    Sailing in Baltimore · 5 guests

    30 ft sailboat with highly experienced Captain in Baltimore Inner Harbor

    5.0
    $150hour
    Let's Go Sail in Gloucester Point, Virginia
    Sailing in Gloucester Point · 6 guests

    Let's Go Sail in Gloucester Point, Virginia

    5.0
    Superowner
    $117-$125hour
    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
    Sailing in Gloucester Point · 6 guests

    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    5.0
    Superowner
    $125hour
    34' Hunter Cruising Monohull In Rock Hall, Maryland United States
    Sailing in Rock Hall · 4 guests

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

    4.5
    $275-$375night
    Sail out of Middle River onboard Hunter 41 AC Sailboat!!
    Sailing in Essex · 6 guests

    Sail out of Middle River onboard Hunter 41 AC Sailboat!!

    5.0
    $175hour
    Charter 42' Lagoon Catamaran in Annapolis, MD
    Sailing in Edgewater · 12 guests

    Charter 42' Lagoon Catamaran in Annapolis, MD

    5.0
    $425hour
    Charter 44' Orana Cruising Catamaran In Deale, Maryland
    Sailing in Deale · 10 guests

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    5.0
    $2,600day
    Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!
    Sailing in Annapolis · 4 guests

    Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!

    5.0
    $150hour
    Melges 24 - One Design Racing Experience Or Charter
    Sailing in Hampton · 8 guests

    Melges 24 - One Design Racing Experience Or Charter

    5.0
    Superowner
    $200hour
    Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail
    Sailing in Saint Michaels · 6 guests

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

    5.0
    $325hour
    Catalina 425 Sailing Yacht in Rock Hall, Maryland
    Sailing in Rock Hall · 6 guests

    Catalina 425 Sailing Yacht in Rock Hall, Maryland

    5.0
    $160hour
    $400 M-Th | $600 F-Su | 13 ppl | Luxury Yacht SLX 400
    Events in Washington · 13 guests

    $400 M-Th | $600 F-Su | 13 ppl | Luxury Yacht SLX 400

    New
    Superowner
    $400hour
    Instant Book
    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
    $150hour
    Experience the Charm of St. Michaels Aboard the 41ft S/Y Selina II Sl - 2 Hours
    Sailing in Saint Michaels · 6 guests

    Experience the Charm of St. Michaels Aboard the 41ft S/Y Selina II Sl - 2 Hours

    New
    $350hour
    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
    $725day

    Top Destinations Nearby

    Sailing Reviews in Virginia

    1. CB

      Caprice

      41' Lagoon Catamaran in Maryland

      This was one of the best rides I’ve had in a while. Captain Jess is communicative, helpful and kind. We went out for 4 hours and had great weather. The boat is clean, he had 2 fridges for our food and drinks, it was nice and spacious, and there were floaties to get out on the water. It was a very enjoyable day.

    2. DB

      Dan

      38' Hunter 376 Cruising Monohull in Annapolis, Maryland

      Capt Alberto and Grace were wonderful hosts. They were very flexible regarding the weather, great teachers of sailing, and were very hospitable and welcoming with their boat. We had an amazing time. Capt Alberto truly loves the sea.

    3. NW

      Nicole

      Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️

      I hosted my 50th birthday on this vessel!! Absolutely, positively an amazing experience! The vessel is absolutely beautiful and spacious. There was plenty of room on this vessel for my 12 guests! The Captain Shane provided excellent customer service throughout the entire trip. He very responsive to any questions that I had !!! If you want an stellar experience, this is the way to go!!!!!!

    4. bb

      brent

      41' Lagoon Catamaran in Maryland

      Captain J was excellent. So nice and accommodating to our requests. It is our second time with him and will book with him again next time we want to have a great day on the water

    5. AL

      Aubrey

      38' Hunter 376 Cruising Monohull in Annapolis, Maryland

      Such a fun guy, storyteller, and enjoyable host! He is a wealth of knowledge and was eager to teach us how to sail. We sailed the whole time!

    6. PG

      Polina

      38' Hunter 376 Cruising Monohull in Annapolis, Maryland

      Thanks to captain Alberto and Grace my birthday became unforgettable! Completely met all our expectations.!

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