Charter Windfall in Gloucester, Massachusetts, this Summer

Windfall under sail in the Bahamas

Windfall under sail

To celebrate 25 years of chartering in Gloucester and the Bahamas, Defiance Sail Charters will be offering 10% OFF on all charters from January 1 through December 31st of 2024. If you reserve a second charter during the year you will also receive 10% OFF.

Hop aboard our classic Hinckley ketch, Windfall.  We (Captains Raffi and Lisa) have been chartering for over 20 years and would enjoy sharing the sailing experience with you. 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.

We dock from June through October in Gloucester’s historic Smith’s Cove, within walking distance to the famed artist colony of Rocky Neck.

Why not join us aboard Windfall in the Bahamas next winter and find out why so many people rate us as “excellent!” From February through May we offer Bahamian island hopping excursions.

Built by Hinckley Yachts in Southwest Harbor, Maine, Windfall is an elegant and comfortable, forty-nine foot sailing vessel. A full array of amenities, a spacious center cockpit and private aft cockpit all contribute to an enjoyable sailing experience. We offer day or overnight crewed sailboat charters. Relax and enjoy a glass of wine, take the helm or hoist the mainsail. It’s up to you.

We have been featured in several publications; Northshore Life, a Goodlife Publication; the Gloucester Daily Times, Business section; and Cape Ann North of Boston Living.

->Check out this great review on TripAdvisorTravelers' Choice 2023

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

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

Day sail options include:

  • Sail to nearby islands to hike and/or swim
  • Sail around Cape Ann through the scenic Annisquam River
  • Historic tour of Gloucester Harbor
  • Tour nearby Rockport and Bear Skin Neck
  • Or consult with Captain Raffi t0 design your own day trip

Defiance Sail charters also offers overnight and multiday seafaring adventures.

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

Gift certificates are available.