Defiance Sail Charters

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211 E Main St
Gloucester, MA 01930
+1 (978) 948-5434
http://defiancesailcharters.com
Windfall, our elegant 49-foot Hinckley 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. www.DefianceSailCharters.com

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Reviews

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5.03 reviews
Photo of McLizzy S.
McLizzy S.
9/7/2025

Take this adventure with your family and friends-you won't regret it! Captains Lisa and Raffi are incredible. They will literally blow you away during your sail - they will teach your children,...

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Nicole K.
8/16/2020

I can't think of a better way then taking off on a private sail with people I love. Everything was seamless, efficient and safe. You are in good hands so all you have to do is enjoy the wind in...

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Jack B.
8/28/2017

This was one of the greatest times I ever had. If you have any thoughts of chartering a sailboat in Gloucester, Massachusetts or The Bahamas, go with Raffi and Lisa.

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