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    Incredible sailboat rentals in Virginia, United States.

    Average of 266 reviews in this area.
    17 listings
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
    hour$150
    Super Owner6 guests

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

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
    hour$150
    Super Owner6 guests

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    "Imi Ola" Seawind 1260
    hour$716
    Super Owner12 guests

    "Imi Ola" Seawind 1260

    J70 Daysailer rental in Hampton
    hour$100
    Super Owner4 guests

    J70 Daysailer rental in Hampton

    41' Lagoon Cruising Catamaran in Maryland, United States
    day$1,849
    12 guests

    41' Lagoon Cruising Catamaran in Maryland, United States

    Charter 44' Orana Cruising Catamaran In Deale, Maryland
    day$2,400
    10 guests

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    Beneteau 41ft Sailing Charter in Annapolis, Maryland
    hour$180
    8 guests

    Beneteau 41ft Sailing Charter in Annapolis, Maryland

    Let's Go Sail in Gloucester Point, Virginia
    hour$90
    6 guests

    Let's Go Sail in Gloucester Point, Virginia

    Sunset Champagne Cruise on the Chesapeake Bay
    hour$399
    6 guests

    Sunset Champagne Cruise on the Chesapeake Bay

    Sailing Charter with USCG Licensed Captain
    hour$150
    6 guests

    Sailing Charter with USCG Licensed Captain

    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 customer reviews for Sailing in Virginia.

    1. rc
      raymond
      38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

      I cannot speak highly enough about Capt. Alberto. He and his ‘first mate’ gave us a great morning on the bay. A chilly but sunny morning with good wind kept us thoroughly engaged in the sailing. The Capt and his wife were easy to spend time with. Their love and knowledge of sailing and their warmth made for good conversation and a relaxing day. The boat is comfortable and well maintained. Even with some stiff breezes we stayed dry. When my wife got chilly, they provided a blanket to keep her warm. Very thoughtful and appreciated. Capt. Alberto gave me the helm for a time and allowed me to sail a beautiful boat. It topped off a perfect day. Thanks Cap! We’ll be back.

    2. Melissa
      Melissa
      38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

      We had the best time with Captain Alberto! He was so nice and professional. His many years of experience is obvious and he shared so much of his knowledge with us. Our time together gave us such a huge appreciation and love of sailing! We can’t wait to go again!

    3. DS
      Dan
      38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

      Capt Alberto and his wife Grace are amazing hosts and people! This was our families first trip on the Getty oat site and we’re happy to choose this one. The boat was in pristine condition and even though there wasn’t much wind the day we went out, the Capt searched and found some! The kids were able to steer and learn about sailing. All in all a perfect morning and would definitely recommend to anyone!

    4. AM
      Amy
      38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

      Captain Alberto was such an amazing host and captain! He and his wife were wonderful hosts, and made our trip even more amazing. We had such a great time and can not wait to go back again for another "girls weekend" or with our family and friends. We will be recommending Captain Alberto to everyone we know!

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

      Captain Alberto and Grace are fantastic! It was fascinating to hear about their backgrounds and what lead them to sailing. They were very accommodating, and the boat was exactly as described. It was such a fun day for everyone. We would absolutely book with them again!

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

      Had a wonderful time with Alberto and Grace. They were kind, friendly, and extremely knowledgeable. My husband and brother in law loved learning some sailing basics. Grace also brought a variety of life jackets for our 2.5 year old daughter. All in all an incredible, relaxing, trip and we look forward to returning in the future!

    GetMyBoat has 17 listings for Sailing experiences in Virginia with 266 reviews.

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