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Defiance Sail Charters - Day Tours

211 E Main St, Gloucester, MA 01930-4161
+1 978-948-5434
Review Highlights
A beautiful day aboard the Windfall!

My coworkers and I recently joined Captain Raffi & Lisa for a 3 hour sail aboard the Windfall. We... read more

Reviewed 1 week ago
Heather C
Adventure in the Abacos!

My wife and I recently joined Raffi and Lisa aboard Windfall in the Abacos. We enjoyed gorgeous... read more

Reviewed 14 April 2017
Becky F
West Townsend, Massachusetts, United States
Read all 84 reviews
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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.We head south in autumn to go sailing in the beautiful, sunny Sea of Abaco from late February through May. Meet us at our base of operations at the fabulous Baker's Bay Club in Great Guana Cay, Abaco, Bahamas. Or, charter Windfall for island hopping anywhere in the Bahamas.
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211 E Main St, Gloucester, MA 01930-4161
+1 978-948-5434

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1 - 10 of 84 reviews

Reviewed 1 week ago

My coworkers and I recently joined Captain Raffi & Lisa for a 3 hour sail aboard the Windfall. We had the most wonderful day! Captain Raffi & Lisa are wonderful hosts - extremely knowledgeable about Gloucester and the surrounding area and incredibly attentive to their...More

Thank Heather C
Reviewed 14 April 2017

My wife and I recently joined Raffi and Lisa aboard Windfall in the Abacos. We enjoyed gorgeous snorkeling spots that made us feel like we were on our own private island! Amazing coral, reef fish, and so many tunnels in that crystal clear water. Lisa's...More

Thank Becky F
Reviewed 11 April 2017

We experienced an absolute departure from the world that we are usually immersed in with the Windfall. The food was so fresh and beautifully prepared . The conch fritters are the best I have ever eaten. The excursions on the dingy brought out the children...More

Thank Louisetiingen
Reviewed 16 March 2017

Capt. Raffi and Lisa are down to earth wonderful hosts, couldn't ask for a nicer crew to spend the day. Every step of the way they were gracious and accommodating. We would sail with them any day!!! Windfall is a Beautiful Boat ,almost as nice...More

Thank Harvey776245
Reviewed 11 October 2016

We had the enjoyment of sailing with Captains Raffi and Lisa in the Bahamas two years ago - a wonderful experience. When our relatives from the West Coast were visiting, we decided a sail with Raffi and Lisa in Gloucester would be a nice adventure...More

Thank Judy F
Reviewed 6 October 2016

The day trip around Gloucester harbor and bay was the best ever. Captains Raffi and Lisa were very gracious hosts and the Windfall is a beautiful yacht. Great company, great stories about the harbor and other sailing adventures. Highly recommended for either a day trip...More

Thank kcf929
Reviewed 16 September 2016

I'm a photographer and chartered with Lisa and Raffi for a photoshoot. They went out of their way to make everything go smoothly and provide me an opportunity to get some fantastic images. The boat is gorgeous!

Thank Erik P
Reviewed 11 September 2016

We sailed with a group of 11. Captains Raffi and Lisa were awesome during our wedding sail. The Windfall was beautiful, absolutely loved this sailboat. It's much more impressive in person than in photos. Lisa was extremely accommodating serving our guests, making sure everything was...More

Thank kmitchell70
Reviewed 5 September 2016 via mobile

Capt. Raffi and his 1st mate Lisa made our group feel special. They are very experienced sailors who's sailboat is in excellent shape. We hired on for a 3 hr sail which seemed to go by quickly. Very relaxing. Highly recommend.

Thank kwkirbo
Reviewed 2 September 2016 via mobile

There were 3 couples traveling in our Rv's on a 3 month trek from California to the Candian Maritimes and New England coast. We all jumped on the chance to have a private sailing experience out of Gloucester. As others have said, Lisa and Raffi...More

Thank WaltandJackie J
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Questions & AnswersAsk a question
What is the cost for a 2 hr. cruise from Gloucester?
21 September 2016|
Response from kwkirbo | Reviewed this property |
Please see their website