Great sailboat rentals near Boston, Massachusetts.

Average of 20 reviews in this area.
14 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.

GetMyBoat customer reviews for Sailing in Boston.

  1. 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!

  2. 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!!

  3. 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

  4. NG
    Nick
    103’ Trilogy Power Mega Yacht Harbor and Islands Charter
  5. JC
    Joel
    City Tour in Boston

    For something a little more different than the norm, definitely spend a little more for a wonderful memory with loved ones. Beautiful scenery, amazing crew and most definitely worth every penny.

  6. BH
    Bruce
    103’ Trilogy Power Mega Yacht Harbor and Islands Charter

    Chartered for an evening cruise around Boston and had a great time. Boat was clean and in good condition and crew was outstanding. I also though the value was excellent for a yacht this size.