Defiance Sail Charters

Defiance Sail Charters Windfall, our 49-foot sailing vessel, is available for day or overnight sailing charters. Come join us aboard Windfall in the Bahamas in the winter.

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. We'll be 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 Gre

at Guana Cay, Abaco, Bahamas. Or, charter Windfall for island hopping anywhere in the Bahamas. Come on down to Windfall in the Bahamas for an exceptional vacation!

10 years ago?!!Looking just the same
08/30/2026

10 years ago?!!
Looking just the same

08/25/2026

Save the date - Boats are needed. Saturday, September 5th for the 2026 Annual Parade of Lights Boat Parade in Gloucester during Gloucester Schooner Festival. Let's celebrate the 250th America, decorate your boats and houses along the route.

Enjoying this beautiful August weather out on the water!
08/25/2026

Enjoying this beautiful August weather out on the water!

Gloucester Schooner Festival is just about two weeks away! ⛵ Visit America's Oldest Seaport this Labor Day weekend for d...
08/22/2026

Gloucester Schooner Festival is just about two weeks away! ⛵
Visit America's Oldest Seaport this Labor Day weekend for deck tours, schooner sails, Maritime Heritage Day, and so much more.
Start planning your visit at www.schoonerfestival.com

Some nice hot weather this summer for charters on-board Windfall!Come join the FUN!!Call Captains Raffi/Lisa - (978) 948...
08/18/2026

Some nice hot weather this summer for charters on-board Windfall!
Come join the FUN!!
Call Captains Raffi/Lisa - (978) 948-5434
https://defiancesailcharters.com/

07/12/2026

Save the day! July 17, 2026✨🪐 A Spectacular Planetary Lineup Is Coming!

Address

211 E Main Street
Gloucester, MA
01930

Telephone

+19789485434

Website

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