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Information
- 1-Cape Ann Vacations
- 2-Massachusetts Vacations
- 3-North of Boston
- 4-Discover Gloucester
Experience the Best Sailing Charters and Boat Tours in Gloucester, MA
Day Sail
Cast off from Beacon Marine Basin and settle in for a narrated tour of famed Smith’s Cove and Gloucester’s Inner
Romantic Sunset Sail and Dinner
Celebrate sunset and/or your special occasion with a three-hour sail and a specially prepared gourmet dinner.
Create Your Own Reason to Sail, Sail, Sail!
Contact Captain Raffi for ideas and rates for Create Your Own Reason to Sail!
Sail Charters
Hop aboard our classic Hinckley ketch, Windfall. We (Captains Raffi and Lisa) have been chartering for over 25 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 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.
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.
Day Sail
Cast off from Beacon Marine Basin and settle in for a narrated tour of famed Smith’s Cove and Gloucester’s Inner Harbors before setting sail to cruise historic Gloucester Harbor and/or beyond.
You will be served complimentary light bites (seasonal fruit, freshly baked goods, hors d’oeuvres) and beverages including:
- juices
- soft drinks
- coffee/tea
- beer and wine
Lunch and/or dinner are available for an additional fee.
We always make accommodations for special dietary requirements.
Alcoholic beverages will be served at the discretion of the Captain, not to exceed one drink per hour.
Minimum two-hour day sails may be extended by one hour increments to your desired cruise time.
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way to celebrate
- Wedding ceremony (by the Captain or your officiant)
- Bachelor/bachelorette party
- Honeymoon
- Birthday
- Reunion
- Engagement
- Anniversary
- Workshop, team building meeting
- Memorial service at sea
- Fireworks
- Divorce
- Create Your Own Reason to Sail!
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 to design your own day trip
Live your unique
sailing experience.
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