The Best Sailboat Rentals in Massachusetts

Sunset Sail Buzzards Bay in a Classic Sloop!

I recently had the pleasure of sailing with Captain Freddie on his boat for a surprise two-hour cruise with my girlfriend, and it was an unforgettable experience. From the moment we stepped aboard, we were treated to breathtaking views of Buzzard's Bay and a sense of tranquility that only the open water can offer. The scenic beauty of the surroundings was truly stunning, and we found ourselves captivated by the serene atmosphere that only a sailboat can provide. Freddie was an absolute delight and contributed significantly to the enjoyment of our trip. His friendly and attentive personality put us at ease, and his passion for sailing was evident throughout the journey. He told us all about his restoration of his boat and made sure we were comfortable and well taken care of. We knew nothing about sailing, and he explained all about how the sails work, answered my endless questions, and his expertise and seamanship were evident. We felt completely safe under his guidance. The overall experience was nothing short of magical. From the sunshine and fresh air to laughing and relaxing on the deck while Freddie told us all about the area and his tales of trips to Martha's Vineyard and beyond. I scored some serious romance points with my lady by booking this trip. I would 100% sail with Captain Freddie again without hesitation.

43' Sailboat, Bristol RI & Beyond

We had a wonderful time with Catian Francis :) He is a lot of fun and makes you feel at home on his yacht. Things wemt very smooth and we can highly recommend having a exceptional sailing experience with him. Heiner

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

Perrin was a great conversationalist as well as a captain for our sunset sail. I appreciated his knowledge about the island and town’s history. He was very accommodating for our needs and patient with us being fulfilling new parent duties! Would recommend

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

I loved my experience going on a boat trip with Kenneth! He’s very professional but also easy going and fun to be around! He was very accommodating with my requests (I’m a photographer and rented the boat for a couple session). I’d 100% recommend his service and I’m already looking forward for a next trip!

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

Kenny and Perrin were fantastic with communication throughout the process of booking and getting us out for a sunset cruise! Our family had a great time with Perrin and he is very knowledgeable about the area and has tons of experience. We felt right at home on Mariah! We will definitely be back. Great boat, great captain, and a great experience all around. Highly recommend. Seth

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

Perrin was amazing! The whole process was such a breeze and we had a great couple of hours out on the water. Really knowledgeable (and we tested him haha) and had great insight about the area and the other boats around us. Would definitely recommend!