The Best Sailboat Rentals in Massachusetts

Elegant 43ft Catamaran: Experience Boston Harbor in Style!

I had a fantastic evening on this beautiful catamaran with a successful proposal to my now fiancee with sunset. Alex was so professional and accommodating, which led to the success. He was fast to respond, accommodating my date change request due to the weather forecast change even though it was within five days. Alex also coordinated well with my photographer, allowing him to board early before picking us up, which kept the proposal a surprise.

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!

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.

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!

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.

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!