Great sailboat rentals near Boston, Massachusetts.

Average of 51 reviews in this area.
9 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.

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.

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GetMyBoat customer reviews for Sailing in Boston.

  1. VF
    Venus
    103’ Trilogy Power Mega Yacht Harbor and Islands Charter

    This yacht is completely gorgeous head to toe! The crew members were wonderful and really went out of their way to make sure we were comfortable and having a good time. We had the best time ever, it was the perfect birthday experience! Above and beyond!

  2. IO
    Ifeoma
    103’ Trilogy Power Mega Yacht Harbor and Islands Charter

    I had such a wonderful experience celebrating my birthday. The crew was extremely helpful and so kind. I would definitely book again! I had so many friends and family inquiring about this boat. Thank you so much for the amazing experience and for making my birthday special.

  3. 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!

  4. ML
    Molly
    Sailing Charters On 36ft Sailboat In Winthrop, Massachusetts Listed Marblehead but traveling to Boston, you will be able to Book from both Locations

    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.

  5. AJ
    Alina
    Sailing Charters On 36ft Sailboat In Winthrop, Massachusetts Listed Marblehead but traveling to Boston, you will be able to Book from both Locations

    Allan was great! Very personable, with plenty of knowledge and life experience in the area. We had the best time celebrating a friend's birthday doing something you don't get to do every day, and it's a great experience if you don't get out on the water often! Highly recommend.

  6. AG
    Angelique
    Sailing Charters On 36ft 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!