Charter “Windfall” in New England

Summer in New England

Happy Memories

Romantic Get-Away

Enjoy Gloucester

Charter Windfall

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Windfall under sail in the Bahamas

Windfall under sail

Sail the Magnificent Coast of New England This Summer!

Charter business will resume June 20th with Covid-19 sanitation guidelines.
Stay safe and be well,Captain Raffi

We dock for the summer season (June through 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.

The ketch, Windfall, is owned by Captain Raffi Kassabian. Built by Hinckley Yachts in Southwest Harbor, Maine, she is an elegant, traditionally styled, forty-nine foot sailing vessel. A full array of amenities, a spacious center cockpit and private aft cockpit all contribute to an enjoyable and comfortable sailing experience.

->Check out this great review on TripAdvisor

We were featured in three publications in 2010; Northshore Life, a Goodlife Publication, Winter 2010; the Gloucester Daily Times, Business section, August 10, 2010; and Cape Ann North of Boston Living, Fall 2010.


Sail in the Beautiful, Turquoise Waters of the Bahamas Next Winter

Windfall, our elegant 49-foot Hinckley yacht, is available for day or overnight crewed sailboat charters in the Bahamas.

Why not join us aboard Windfall in the Bahamas, next winter and find out why so many people rate us as “excellent!” Meet us at our Bahamas base of operations in Georgetown, the Exumas, from February through May. Or, charter Windfall for an island-hopping vacation anywhere in the Bahamas.

Come on down to Windfall in the Bahamas for an exceptional chartering experience!

Follow the crew of Windfall on their Blog.
Better yet, why not join them!

Gift certificates are available.


Being aboard defiance sail charters is a unique and special way to celebrate:

2018 Certificate of Excellence ~ Tripadvisor
  • Wedding ceremony (by the Captain or your officiant)
  • Honeymoon
  • Birthday
  • Reunion
  • Engagement
  • Anniversary
  • Divorce
  • Fireworks
  • Bachelor/bachelorette party
  • Workshop, team building meeting
  • Memorial service at sea, or
  • Create Your Own Reason to Sail! Check out these ideas!

defiance sail charters B&B is also a great lodging alternative to staying in a hotel or an inn.

So “hoist the main,” take the helm, trim the sails, or just relax and be catered to as Windfall slips gently through the waters of Gloucester Harbor or the Bahamas and beyond.