Great sailboat rentals near Boston, Massachusetts.

Average of 22 reviews in this area.
12 listings

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.

Using GetMyBoat to rent your next sailboat.

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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. CP
    Cristal
    Charter 50ft "Frayed Knot" Cruising Monohull In Manchester-by-the-Sea, Massachusetts

    This was the highlight of our entire trip. Claude and his wife are extremely knowledgeable and amazing hosts. We got to see amazing structures and islands and even learned some interesting facts. We got to swim and enjoy the beautiful waters. Claude even let some of us drive the boat (with supervision of course.) To top it all off we even got some complimentary goodies including some coozys and pens! Their hospitality was so incredible that it felt like we all knew each other for a long time. I will absolutely be booking the Frayed Knot next time we make this trip. Thank you again Claude and Judy!

  2. MF
    Michelle
    103’ Trilogy Power Mega Yacht Harbor and Islands Charter

    Had a blast! Very comfortable for kids and Adults. The crew was extremely accommodating and made it that much better. Owner was helpful with all questions and even brought a wagon out to our car to carry our things easier. Sunset was beautiful. Crew had our drinks on ice and music bumping! Only downfall..my husband now wants to buy a yacht!

  3. LO
    Laura
    City Tour in Boston

    As new Boston residents it was stellar to experience the city from the harbor. Peter was very responsive from the beginning. The boat was beautiful! I highly recommend.

  4. AG
    Angelique
    Sailing Charters On 36ft "Emma Rose" Sailboat In Winthrop, Massachusetts Listed Marblehead but traveling to Boston, you will be able to Book from both Locations

    We had such a wonderful time aboard the Emma Rose with Captain Allan! We took my father for his birthday, in May and had such a wonderful time! We were able to pack a picnic, and were able to get really hands on with the sailing, and learned so much! The trip was so relaxing and refreshing! My dad still talks about how wonderful that day was, and how much he learned! Captain Allan is great with communication before hand as well, and answered all our questions promptly! We had an amazing sail around the north shore and are looking forward to planning our next sail with Captain Allan! We would highly recommend!

  5. LD
    Lisa
    City Tour in Boston

    Peter was an excellent captain and made my husband's 60th birthday sail fantastic! Peter helped me organize food and drinks for the trip and customized our day based on what my husband wanted. Highly recommend this boating experience!!

  6. JK
    Joseph
    65ft "Macgregor" Independence Sailboat Charter in Salem, Massachusetts

    Thank you Captain Lloyd for a wonderful day out. The "Independence" is very well maintained, so clean and everything ship shape, and both you and you're crew Bernie were knowledgeable and fun to be around. What a day! Caterina and Joe