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Page 1 of 1 • 24 listings
14
Barnstable
Massachusetts
29
Cape Cod
Massachusetts
16
Middletown
Rhode Island
19
Newport
Rhode Island
40
Quincy
Massachusetts
19
Jamestown
Rhode Island
11
Hull
Massachusetts
7
Chatham
Massachusetts
21
Narragansett
Rhode Island
56
Boston
Massachusetts
8
Marblehead
Massachusetts
11
Gloucester
Massachusetts
46
Montauk
New York
46
Sag Harbor
New York
50
Noyack
New York
74
Southampton
New York
7
Lake Winnipesaukee
New Hampshire
62
Long Island
New York

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.
KS
Kevin
Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat
What an amazing trip. I’ve been coming to the waters on the Vineyard for years and Mason took us to places I’ve never seen before. The boat was perfect for a relaxing adventure. I would highly recommend for almost any type of group from a couple to a family or a small group. What an experience !
TI
Tony
Fairhaven/New Bedford Escape – 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.
SM
Sarah
Yamaha 195S Wakeboat in Sandwich MA
Caleb was incredibly helpful! He came to pick us up by boat and brought us back right in front of our house. He knew all the best spots in the area to stop for a nice lunch. His boat is very comfortable, and he was also great with our little girl. We 100% recommend him !

Dhuvi
Yamaha 195S Wakeboat in Sandwich MA
If this is the only review you read, all you need to know is that you wont find a better boat or boat renter. The 195s is an insanely fun ride and very beginner friendly (rare combination) and Caleb has excellent communication and is super accommodating. Youd be hard pressed to find things that could have made our experience better.
RA
Rob
Yamaha 195S Wakeboat in Sandwich MA
It took a little learning to use the GetMyBoat website/app. Boat owner Caleb W. was very responsive to messages. You won’t have to wait long to hear from him, most often in minutes, and that didn’t change after the booking. He was prompt in meeting at the boat ramp and the end of the rental day. He was very helpful to accommodate where we wanted to put in the boat in Waquoit Bay or Barnstable Harbor. With the little extra time Caleb provides over the ‘boat rental businesses’ elsewhere, we could cruise more leisurely between Waquoit Bay and Falmouth area and still enjoy anchoring in the shallow water of Washburn Island to enjoy getting in the water. Try to do your boating in waters under 2 1/2 foot seas to enjoy the front of the boat.