Book your charter now to assure the dates you desire!

We dock for the summer season (June–October) in historic Gloucester, Massachusetts at Beacon Marine Basin, in Smith's Cove, within walking distance to the famed artist colony of Rocky Neck. Departures can be arranged from any accessible port in New England for an additional fee.

Windfall's B&B (Boat & Breakfast dockside) is a great lodging alternative to staying in a hotel or an inn.

Rates are for the boat, captain and crew, not per person and based on 1 to 6 passengers.

For information on additional passengers contact Captain Raffi at: or call 978.948.5434.

Hammond Castle   

Depending on the duration of your charter, prices will include complimentary morning fruit, freshly baked goods, or light hors d’oeuvres and beverages including; juices, soft drinks, coffee/tea, "house" beer and wine.

Of course, accommodations will be made for special dietary requirements.

Alcoholic beverages will be served at the discretion of the Captain.

    romantic getaway

Romantic Getaway

Sail into Sunset with Dinner for two and a B&B aboard "Windfall" dockside.

You'll set sail for sunset at 5pm while being served an hors d'oeuvre, dinner, dessert and beverages (soft drinks, "house" beer and wine, coffee/tea).

In the morning you'll enjoy a leisurely breakfast of freshly baked goods, seasonal fruit, juice and coffee/tea before a 10am departure.

Weeknights (Sunday-Thursday)

Weekends (Friday, Saturday and holidays)

Gratuities are not included. At least 20% is recommended.

Day Sails

3 hours
5 hours
8 hours

Fridays, Saturdays, Sundays, and Holidays: 
3 hours
5 hours  
8 hours

We offer complimentary light hors d'oeuvres, soft drinks,"house" beer and wine. Lunch is available for an additional fee.

Passengers are responsible for any damages to, and/or theft from, the vessel during charter.

Ken and Amy's Wedding

Overnight Sails

(does not necessarily mean being underway throughout the night)

One night (10:00 am–2:00 pm the following day; approximate times) for 2 passengers
Additional nights, extra
Additional passenger, extra

Weekend (Friday, Saturday and holidays):
second night, double occupancy.
Additional passengers, extra

Breakfast, lunch, dinner, and beverages are included. Click here for Sample Menus for overnight and week-long charters.

Meal costs ashore are the financial responsibility of the passengers. Rates do not include dockage/mooring fees.

Gratuities for the First Mate are not included--20% is recommended.

Contact Captain Raffi for possible itinerary.

Relax and Enjoy


B&B (Boat & Breakfast) Dockside in Gloucester

Windfall remains docked at Beacon Marine Basin in Smith's Cove, walking distance to Rocky Neck. You'll be greeted with hors d'oeuvres and chilled, sparkling wine. In the morning, enjoy a leisurely breakfast of freshly baked goods, seasonal fruit, juice and coffee/tea. 10 AM departure.

2 passengers, standard rate
Additional passenger, extra
(Five passengers or less)

Weekends (Friday, Saturday and holidays).

Gratuities for the B&B are not included. At least 10% is recommended.

Sunset   Sunset

Sight See the Stars

woman with starfish   fireworks

Sail, Sail, Sail!

Yes, you can fish from a sailing vessel!

"No fuss, no muss"; the Captain does the filleting! Bringing your personal fishing gear is encouraged.

Gone Fishin'


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little girl
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Kings of the World
enlarge viewat the winch
enlarge viewfour ladies
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