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    Find Sailboat Rentals Near You

    Average of 186 reviews in this area.
    1 - 18 of 49 listings
    Annapolis Sailing on a 34' Beneteau Sloop!
    hour$150
    6 guests

    Annapolis Sailing on a 34' Beneteau Sloop!

    Get away for a day or weekend! Charter 44' Catalina Sailboat!
    day$490
    6 guests

    Get away for a day or weekend! Charter 44' Catalina Sailboat!

    Learn to Sail in Havre de Grace, MD (Minutes off of I95 in Historic Havre de Grace, MD)
    person$200
    2 guests

    Learn to Sail in Havre de Grace, MD (Minutes off of I95 in Historic Havre de Grace, MD)

    Pearson 26 Coastal Sailboat in Norfolk
    hour$60
    6 guests

    Pearson 26 Coastal Sailboat in Norfolk

    #1 Manhattan Luxury Sailboat, Champagne & Catering Service, 5-Star Accommodations
    hour$325
    Super Owner6 guests

    #1 Manhattan Luxury Sailboat, Champagne & Catering Service, 5-Star Accommodations

    Jeanneau 39i Julia Sailing Yacht in NY Harbor
    hour$350
    6 guests

    Jeanneau 39i Julia Sailing Yacht in NY Harbor

    Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC
    hour$300
    6 guests

    Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC

    Sailing Long Island Sound with Captain Steve
    hour$225
    6 guests

    Sailing Long Island Sound with Captain Steve

    Boat Island Historical Tour in Atlantic
    person$45
    1 guest

    Boat Island Historical Tour in Atlantic

    Hobie One 12 Sailboat for rent in Sag Harbor
    day$179
    3 guests

    Hobie One 12 Sailboat for rent in Sag Harbor

    Hunter 27 Sailing Charters in Toronto
    hour$116
    6 guests

    Hunter 27 Sailing Charters in Toronto

    Able Custom 42' Chartered Sailing Experience in Stonington, CT
    hour$215
    3 guests

    Able Custom 42' Chartered Sailing Experience in Stonington, CT

    Tandem Sail on TWO Classic Sailboats (Or Just Charter One)
    hour$175
    12 guests

    Tandem Sail on TWO Classic Sailboats (Or Just Charter One)

    Sail Newport Rhode Island with Captain Kurt on 36' Pearson Sailboat
    hour$250
    6 guests

    Sail Newport Rhode Island with Captain Kurt on 36' Pearson Sailboat

    Fun 23' Sonar Sail Boat for Up to 5 Guests
    hour$200
    5 guests

    Fun 23' Sonar Sail Boat for Up to 5 Guests

    Sail Gloucester Harbor and Beyond Aboard Catalina 36 MKI Sailing Yacht!!
    hour$225
    6 guests

    Sail Gloucester Harbor and Beyond Aboard Catalina 36 MKI Sailing Yacht!!

    49 results

    Boating Guide - Sail

    Time to set sail in the most beautiful locations in the world.

    Rent or charter a sailboat for your next water experience. Whether you're looking for a small sailboat, a luxury sailing yacht, a catamaran, or a racing sailboat, you're sure to find the perfect vessel for your desired experience on GetMyBoat. Sailboat rentals are a great way to explore if you're traveling to top sailing destinations like the Chesapeake Bay, Mission Bay, Lake Tahoe, or Cape Cod. Book a sailboat to fit your budget and itinerary with GetMyBoat.

    GetMyBoat customer reviews for Sail in this area.

    1. AL
      Ariel
      #1 Manhattan Luxury Sailboat, Champagne & Catering Service, 5-Star Accommodations

      Amazing boat! Amazing vibes! Booked with Captain Martin for my friend's surprise bridal shower. He was communicative and very accommodating. Our original date got rained out and Martin communicated with me efficiently and effectively to find a new date. We ended sailing with a his colleague Capt Malcolm on the new date. Malcolm was knowledgeable, fun, and overall had great vibes. He had extensive knowledge about the history of New York, architecture, and pointed out interesting landmarks as we sailed around the harbor. The first mate, Jayden was so helpful as well, helping us onto the boat, getting us drinks, making sure we were warm enough. Such a wonderful experience! Have been recommending Capt Martin, Capt Malcolm, and the whole crew to everyone!

    2. KO
      Katherine
      #1 Manhattan Luxury Sailboat, Champagne & Catering Service, 5-Star Accommodations

      Run don’t walk to this boat! We are all New Yorkers and had the best time. Amazing service and great day on the water

    3. ML
      Maxine
      #1 Manhattan Luxury Sailboat, Champagne & Catering Service, 5-Star Accommodations

      Incredible time! Martin and his first mate were amazing hosts - offering us blankets and extra windbreakers in the cold, taking multiple photos for us, and making sure we knew we could play music during the trip. Truly great hosts that I couldn't recommend more!

    4. Stephanie
      Stephanie
      Sailing Long Island Sound with Captain Steve

      Steven was absolutely wonderful! Great communication - very accommodating - spectacular boat! I highly recommend!!

    5. Debra
      Debra
      Get away for a day or weekend! Charter 44' Catalina Sailboat!

      We had an awesome time on Captain John's sailboat. He was the perfect host - safe, engaging, experienced, informative, and fun. We could not have asked for a more perfect afternoon on such a beautiful sailboat. We will definitely be back to sail again! Highly recommend. P.S. Also lots of laughs :)

    6. AL
      Alyson
      Get away for a day or weekend! Charter 44' Catalina Sailboat!

      We had a great day on the water with Jack! He is an absolute expert sailor with a gorgeous sailboat. He was accommodating from beginning to end and I definitely would go on his boat again. I highly recommend Jack and I am glad I connected with him through this website. Shoutout to first mate Jeff!

    GetMyBoat has 49 listings for Sail experiences in this location with 186 reviews.

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