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    Great sailboat rentals near Boston, Massachusetts.

    Average of 53 reviews in this area.
    6 listing

    Boating Guide - Boston Sailing

    Step onboard a sailboat for an unforgettable experience in Boston, Massachusetts.

    Get ready for a fun adventure when you hit the open water onboard a sailboat in Boston, Massachusetts. 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. Boston, Massachusetts is a wonderful sailboat rental destination.

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

    GetMyBoat customer reviews for Sailing in Boston.

    1. LM
      Laura
      I offer sailing charters on Cal 36 Sailboat. We sail around the islands of the Gold Coast of Boston’s north shore. I will come to Boston ,if I am available on your charter date.

      Capt Al was excellent - the boat fit our party of 7 nicely! We enjoyed the sail and talking with him. Communication pre-sail was great. Unfortunately our sail was shortened by an hour because of foggy weather causing us to miss the first hour. Other than that, we were very happy. Hope to be back.

    2. Melissa
      Melissa
      I offer sailing charters on Cal 36 Sailboat. We sail around the islands of the Gold Coast of Boston’s north shore. I will come to Boston ,if I am available on your charter date.

      Captain Allan was absolutely fantastic. The sail was beautiful and comfortable and he was extremely friendly, gives you background on the MA area you sail around and overall just a fantastic experience. Our sail with him was the highlight of our weekend. Highly recommend!

    3. NG
      Nicole
      I offer sailing charters on Cal 36 Sailboat. We sail around the islands of the Gold Coast of Boston’s north shore. I will come to Boston ,if I am available on your charter date.

      I booked this as a 10 year wedding anniversary gift for my husband. Captain Allan was extremely friendly, knowledgeable, and took us out on an unbelievable, unforgettable experience. I was thrilled with the whole thing - from inquiring about the trip, so when we came back on the dock. He was incredibly easy to work with, responsive, and when we got on board, he made us feel safe, and like we were old friends. If possible, we will absolutely do this again! Thank you for everything Captain Allan!

    4. PA
      Perry
      I offer sailing charters on Cal 36 Sailboat. We sail around the islands of the Gold Coast of Boston’s north shore. I will come to Boston ,if I am available on your charter date.

      Captain Al was such a delight to sail with. He was extremely friendly, an excellent communicator leading up to and during the trip (and was also a fantastic teacher for those in the group that were curious to know more about sailing). We had such an amazing time, and would definitely want to take a trip with Captain Al again in the future. (I also lost my phone on the boat, and Al was incredibly patient and kind in helping me find it again at the end of our trip--thank you again, Captain Al!!)

    5. MU
      Morgan
      I offer sailing charters on Cal 36 Sailboat. We sail around the islands of the Gold Coast of Boston’s north shore. I will come to Boston ,if I am available on your charter date.

      We had a great trip with Captain Allen. There wasn't a lot of wind, but he was working valiantly to catch any breeze that came our way. I also loved that he made it an interactive trip by allowing us to help out with various tasks. Captain Allen was knowledgeable, friendly and told great stories to make our trip memorable.

    6. Molly
      Molly
      I offer sailing charters on Cal 36 Sailboat. We sail around the islands of the Gold Coast of Boston’s north shore. I will come to Boston ,if I am available on your charter date.

      I would definitely recommend Captain Allan and Boat Emma Rose to my other friends. This was such a great experience and we had so much fun on sea. Captain Allan is very experienced and friendly, we also steered the boat a while on the sea. The boat is clean and nice.

    GetMyBoat has 6 listing for Sailing experiences in Boston with 53 review.

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