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Page 2 of 2 • 48 listings
AB
Alan
Dom was a great host. He went above and beyond. We have nothing but good things to say about our experience. Ot was a great experience and we would definitely recommend it for anyone visiting the area or locals just wanting to get out on the water and enjoy the beautiful views.
DK
Dmitri
Charter 36ft Sloop In Westbrook, Connecticut
We had a fantastic 2-hour sail out of Westbrook! The boat was in great shape, and Captain Joy was a Joy to sail with: she was professional, friendly, and very experienced. She made us feel safe and relaxed the entire time, and even shared some interesting local facts and recommendations along the way. The views were beautiful and the whole trip was smooth and enjoyable. Highly recommend booking with this captain – we’ll definitely be back!
WB
Wayne
Captained Sailboat Charter in Salisbury 2 hr sails 4 persons
I really appreciate how Captain Nina accommodated me last minute after I had a lesson scheduled at a sailing school. Saved my plans for the weekend. She did a great job adjusting the experience to my level, and keeping the whole time chill and conversational.

Mayuri
Sag Harbor 73ft Luxuriously Custom Schooner Private Sailing Experience
If you are looking for an amazing time, do not hesitate booking the Luna! Toby and his staff take care of you every step of the way. The boat is well equipped with servingware, water, and ice for your event. Fun bean bags are plenty aboard. Our guests enjoyed the awning and swim spot on a hot day, as well. Just a fabulous experience from start to finish!
PM
Prince
Affordable Yacht 27' Doral in Toronto
Had an amazing experience on the yacht — but honestly, the real highlight was the captain. Super friendly, very patient, and knew exactly where to go for the best views and photos. Even when we were running late, he didn’t rush us at all and made sure we still got the full experience. You can tell he genuinely cares about giving people a good time, not just finishing the trip. If you’re booking this, you’re in safe hands. Highly recommend.
BG
Ben
Affordable Yacht 27' Doral in Toronto
Gino and his dad took us out on their boat to the island off the city, where they anchored and we could swim into the beach. We got amazing views of the skyline on the way, and then on the way back they took us even closer to the city before looping back to the dock. Great experience!