Incredible sailboat rentals in Massachusetts, United States.

Sailing Reviews in Massachusetts

1. JR

   James

   43' Sailboat, Bristol RI & Beyond

   Captain Francis is very personable, and a great host on the water. He has taken very good care of his yacht, which is comfortable, ample in space and comfort, and everything operates as expected. He has a warm and laid-back demeanor, which makes for a very nice chemistry while sailing. Overall an A+.

2. BH

   Betsy

   Luxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in Boston

   Oh what a night! We had a fantastic time on our sailing trip with Jake and his crew. They picked us up right on time, we had a perfect sale, and they even gave us some extra time at the end. The views of Boston were perfection, the sale was smooth and we felt very well taken care of by the entire crew the whole time! It really could not have been any more perfect. We highly recommend!

3. 

   Angela

   63' Catamaran - Newport, RI - Luxury sailing for large groups!

   We had an amazing time on the Heron - the boat and its amenities were perfect for a large group. The crew provided great service and the itinerary and swimming off Jamestown was perfect for those of all ages. We highly recommend this experience!

4. KS

   Kevin

   Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

   What an amazing trip. I’ve been coming to the waters on the Vineyard for years and Mason took us to places I’ve never seen before. The boat was perfect for a relaxing adventure. I would highly recommend for almost any type of group from a couple to a family or a small group. What an experience !

5. LF

   Lena

   Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Sailboat

   Amazing trip! Eric was fantastic. He asked us what we wanted to do, and he took us to his favorite spots. We went swimming and jumped off rocks. He told us very interesting stories and was extremely friendly. He made the whole experience better. He made us feel like the boat was our own. Great time, amazing boat. I’d definitely book him again!

6. JF

   Jason

   43' Sailboat, Bristol RI & Beyond

   Captain Francis was fantastic! The boat was great, the trip into and around the bay was wonderful, and we had an amazing evening on the water!