The Best Boat Rentals Near Martha's Vineyard

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.

28ft Whitewater Center Console Rental in Mashpee, Massachusetts

We were very impressed with Capt Mike! His communication was impeccable! Incredibly responsive! His boat was very clean! He was very kind and understanding. He took us on a lovely tour out of Mashpee! We couldn't have asked for a better experience. Would HIGHLY recommend hiring Capt Mike for your charter. Seriously an amazing afternoon.

8 Person Center Console Rental in Osterville Massachusetts

Bill was the best captain. He was attentive and wanted to make sure everyone was happy and doing what they wanted. We had a mixed age group but they all enjoyed it. Seeing MV from the water and relaxing on the beach in Chappy was a highlight! We definitely recommend Bill!

8 Person Center Console Rental in Osterville Massachusetts

We had such a fun time with Captain Bill! This was the perfect outing for our group of 7. Captain Bill had great music and a very clean boat. Awesome time overall. We would recommend Captain Bill to anyone looking to have a fantastic day on the water.

8 Person Center Console Rental in Osterville Massachusetts

Bill was very gracious and accommodating. He shared his knowledge and enthusiasm for the water with our young children and us equally well. We had an amazing afternoon that included catching fish and seeing some beautiful and secluded spots - in both Cape Cod and Martha’s Vineyard.

8 Person Center Console Rental in Osterville Massachusetts

2d time with Captain William and once again, he did not disappoint. Took 6 kids with us and we had a blast tubing and fishing. We all left with huge smiles on our faces and lifelong memories. William was a true pro, accommodating, and a fabulous tour guide.