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About Defiance Sail Charters
Windfall, our elegant 49-foot sailing vessel, is available for day or overnight sailing charters.We dock for the summer season (June–October) in historic Gloucester, MA, in Smith's Cove, within walking distance to the famed artist colony of Rocky Neck. Summer charters are also available out of Boston or any accessible New England port. Or, use Windfall as your floating B&B (Boat & Breakfast dockside) while visiting the lovely Cape Ann region. In autumn we head south to go sailing in the beautiful, sunny Bahamas from late February through May. Meet us at our base of operation, Abaco, Bahamas. Or, charter Windfall for island hopping anywhere in the Bahamas. We practice all state and local covid-19 sanitation guidelines.
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george r wrote a review Aug 2021
Hopkinton, Massachusetts16 contributions10 helpful votes
Great day with a group of Hopkinton Seniors. Raffi and Lisa are the Best. Everything was Perfect . A Fun day. Hats off to Brie for helping out also.
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Date of experience: August 2021
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Wander79544 wrote a review Aug 2021
Rockport, Massachusetts7 contributions13 helpful votes
I just took my wife out on the Windfall for her birthday. The day far exceeded our expectations of a wonderful sail. The boat is a classic, very beautiful, seemingly easy to handle (they let us steer!), and comfortable. Capt. Raffi and His first mate, Lisa, are two very nice and very competent people. The sailing was beautiful and impressive and fun and we were treated like royalty; they even supplied a birthday cake and we had a little party. We cannot say enough good and nice things about this trip. If you want to sail on a wonderful yacht out of Gloucester, you cannot go wrong with this...really!
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Date of experience: August 2021
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lucyallsn wrote a review Aug 2021
Cleveland, Ohio38 contributions31 helpful votes
We had a great day with the four adults and 4 kids (7-13) on the boat with Raffi & Lisa! Raffi was awesome with the kids - super friendly and kept them busy telling them about the history of Gloucester and the surrounding areas, snacks and juice boxes, knot tying and helping with the sails. he also had a great visitor book they could color a photo to remember their day. it was a nice big bit with bathroom perfect for the size of our party. they were very accommodating even moving up our sail time last minute to account for incoming weather. We’ve been visiting Gloucester for 40 years and this was a first for us! Highly recommend!
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Date of experience: August 2021
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marilyn monroe wrote a review Aug 2021
Greenwich, Connecticut8 contributions
We did the whale watch tour, the water taxi, and ended our day in Gloucester with this cruise at sunset. It was perfect and we are so happy we did! Captain Raffi and Lisa were fun, hospitable, and gave us a great time out on the water. They are an easy crew - full of stories, and well informed on history. It felt like we were on a cruise with old friends! I’ll likely sail with them again. Certainly recommend!
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Date of experience: August 2021
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BostonTripper wrote a review Jul 2021
Boston37 contributions9 helpful votes
We had a great sail with Raffi & Lisa on Fathers Day this year (2021). Captain Raffi was excellent with our two children - he kept them busy & engaged and they were helping to sail which was so fun for them. The boat pretty comfortably fit the 6 of us, and they served drinks and had some small snacks. Our kids did end up getting a little sea sick, but they did great during the 3 hour sail, and the captain quickly turned the boat back into calmer waters. A very nice/relaxing afternoon. Would definitely recommend.
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Date of experience: June 2021
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