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    Find Sailing Charters Near You

    Average of 2,907 reviews in this area.
    19 - 36 of 180 listings
    41’ Bristol Sailboat Charter in Solomons Island, MD
    hour$90
    6 guests

    41’ Bristol Sailboat Charter in Solomons Island, MD

    Starratt & Jenks Morgan 45ft Sailing Charter in Havre de Grace, MD
    day$1,000
    6 guests

    Starratt & Jenks Morgan 45ft Sailing Charter in Havre de Grace, MD

    Charters 33' Cape Dory Cruising Monohull In Kilmarnock, Virginia
    hour$75
    4 guests

    Charters 33' Cape Dory Cruising Monohull In Kilmarnock, Virginia

    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
    hour$125
    6 guests

    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    Let's Go Sail in Gloucester Point, Virginia
    hour$125
    6 guests

    Let's Go Sail in Gloucester Point, Virginia

    J70 Daysailer rental in Hampton
    hour$100
    Super Owner4 guests

    J70 Daysailer rental in Hampton

    Charter 35ft Sailboat In Lacey Township, New Jersey
    hour$100
    6 guests

    Charter 35ft Sailboat In Lacey Township, New Jersey

    Luxury Beneteau 411 Sailing Yacht in Lacey Township
    hour$100
    6 guests

    Luxury Beneteau 411 Sailing Yacht in Lacey Township

    Captained Sailing Adventure in Lacey Township
    hour$119
    6 guests

    Captained Sailing Adventure in Lacey Township

    Sail Away Barnegat Bay! Book the 3-Hour Sail Tour with 35' Sailboat
    hour$150
    6 guests

    Sail Away Barnegat Bay! Book the 3-Hour Sail Tour with 35' Sailboat

    2006 Hunter 44’ Sloop Sailing Charter In Island Heights, New Jersey
    hour$110
    6 guests

    2006 Hunter 44’ Sloop Sailing Charter In Island Heights, New Jersey

    Hobie Getaway Sailing Catamaran in Lavallette
    hour$100
    5 guests

    Hobie Getaway Sailing Catamaran in Lavallette

    Caribbean Vibez on a Brooklyn Sailboat
    hour$191
    Super Owner4 guests

    Caribbean Vibez on a Brooklyn Sailboat

    Set sail on NY Harbor aboard this beautiful and luxurious Ericson sloop!
    hour$223
    6 guests

    Set sail on NY Harbor aboard this beautiful and luxurious Ericson sloop!

    Sail NY Harbor's Newest Sailboat - as seen on CBS News New York!
    hour$285
    6 guests

    Sail NY Harbor's Newest Sailboat - as seen on CBS News New York!

    LEARN TO SAIL on THE MOOSE!
    hour$180
    4 guests

    LEARN TO SAIL on THE MOOSE!

    100+ results

    Boating Guide - Sailing

    Set sail with GetMyBoat - enjoy a sailing charter.

    Hit the open water in style on a sailing charter. Sailing charters with a professional captain are a relaxing way to get on the water and travel by wind power. A sunset sailing cruise, cocktail cruise, or other sailing adventure can make for the perfect experience on a lake or the ocean. Most larger sailboats (typically 18+ feet) also use an engine for longer sailing trips. GetMyBoat has all types of sailing charters and you can build a custom itinerary to plan the sailing holiday of your dreams. From hourly, half-day, full-day or overnight sailing excursions, you are sure to create memories that will last a lifetime.

    Using GetMyBoat to rent your next sailboat.

    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 safety checks on each rental transaction.

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

    Things to consider when booking a sailboat rental or charter.

    • Sailboats range in size and carrying capacity, so check with the captain to make sure the boat you pick will meet your needs.
    • If you want to learn some sailing techniques, ask about instruction or lessons while you're onboard.
    • Any doubts about booking your sailing adventure? No problem! Simply message the captain and ask any questions you may have.

    GetMyBoat customer reviews for Sailing in this area.

    1. AH
      Andrae
      Caribbean Vibez on a Brooklyn Sailboat

      Captain Johnny is a first class host! He is very knowledgable and communicative. My lady as I had a beautiful time. Boat was clean and comfy! Please support him! You won't regret it! Much love and respect to Captain Johnny!

    2. Melissa
      Melissa
      Sail New York's historic waterways aboard Water Music, a classic, semi-custom 40 foot Passport yacht.

      Great experience! Knowledgeable and friendly captain!

    3. SR
      Sabina
      Sail NY Harbor's Newest Sailboat - as seen on CBS News New York!

      the captain was amazing! jessica responded within 30 mins each time i texted her. amazing. 100/10 . will come back again

    4. AV
      Avrohom
      Sail Away Barnegat Bay! Book the 3-Hour Sail Tour with 35' Sailboat

      Was awesome! Strongly recommended

    5. EM
      Erin
      Charters 33' Cape Dory Cruising Monohull In Kilmarnock, Virginia

      Our trip was just perfect. We were looking for a true sailing experience, and Captain Russ gave us that. My husband was at the wheel almost the entire trip, talking all things sailing Capt Russ. Meanwhile I enjoyed the sun and sounds of the water against the boat and the wind in the sails from up front. It was a peaceful and enjoyable trip, despite the wind giving out on us towards the end. We'd book with Captain Russ again in a heartbeat!

    6. Thomas
      Thomas
      Charters 33' Cape Dory Cruising Monohull In Kilmarnock, Virginia

      Captain Russ was just ideal for our half day on the bay! Super pleasant and communicative; completely adaptive to whatever we were up for. The Joie de Vie is ship-shape and the perfect vessel for the Chesapeake Bay. I’ll go ahead and credit him with steady 5-6k winds All day also- just a perfect day. No doubt we will be back for more- thanks again, Captain Russ!

    GetMyBoat has 180 listings for Sailing experiences in this location with 2,907 reviews.

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