Incredible sailboat rentals in Massachusetts, United States.

Sailing Reviews in Massachusetts

1. 

   Jen

   Cal 36 Sailboat Rental in Marblehead, Massachusetts

   My sister and I had a wonderful time with Captain Allan and we had perfect weather all day. He was very knowledgable about the local area and a very skilled captain, making us feel comfortable throughout the whole experience. We played music and had such a great time talking with him. Would absolutely recommend and definitely use Captain Allan again.

2. JS

   Janessa

   63' Catamaran - Newport, RI - Luxury Sailing For Large Groups!

   Thank you so much for having us last night! It was truly the BEST boat experience any of us had ! The Captaint and Kiki were the best hosts ! Super helpful and fun !! They exceeded our expectations and the boat was amazing ! Will definitely make this a yearly thing !!!

3. 

   Kasheena

   Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

   Yesterday’s sailing experience was simply amazing. The captain and crew went above and beyond to take care of our family and make sure all of our needs were met. Even when we were caught up in the moment, they made sure to point out the incredible sights and beauty of the Vineyard so we would not miss a thing. Their kindness, attention to detail, and genuine care made the whole experience unforgettable. We had such a wonderful time and will definitely charter with them again when we return.

4. 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!

5. 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! 🚤⛵️

6. 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!