Incredible sailboat rentals in Massachusetts, United States.

Sailing Reviews in Massachusetts

1. 

   Mike

   Elegant 43ft Catamaran: Experience Boston Harbor in Style!

   Perfect way to spend a day in Boston Harbor. The crew was so incredible and took amazing care of us. They had everything we would need, including snacks and towels (we usually bring our own, but totally didn't need to!). Would 100% recommend for a relaxing time on the water!

2. cC

   chris

   43' Sailboat, Bristol RI & Beyond

   This was an incredible sail. We had to cancel our initial trip due to very bad storms with 65 knot winds and flooding rains early in the season. We rebooked and had a fabulous, relaxing time. The Capt' is both entertaining and a wealth of information and just makes the entire experience what you would want.....sublime.

3. BA

   Bridget

   Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

   Our sail with Captain Perrin was an absolute dream. We were lucky enough to have gorgeous weather for our sunset sail and Perrin could not have been more accommodating. Our bachelorette party of five loved his historic tidbits and great vibes. Would definitely book again when back in the area!

4. AH

   Anne

   43' Sailboat, Bristol RI & Beyond

   Four of us had a great sail with Captain Francis. He struck the right balance between chatting with us and letting us talk amongst ourselves. We wanted to sail by a specific area and he graciously complied. I thought the value for the sailing experience was great. Highly recommend.

5. MH

   Melissa

   Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

   We had a great trip with Kenny - highly recommend. Very prompt, communicative, and clear in departure directions. We had a great sail with beautiful conditions and Kenny is personable and knowledgeable. Highly recommend for a great time on the water, we’ll definitely go sailing with him again next time!

6. SC

   Steven

   Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

   This wasn’t just a sail—it was an adventure filled with stories, laughter, and the kind of peaceful moments you only find out on the water. I can’t recommend Kenneth highly enough if you’re looking for a memorable and truly enjoyable sailing experience. Highly recommend! 🚤⛵️