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, $75 per each additional passenger up to 12.

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 sail & dinner

Celebrate sunset and/or your special occasion with a three hour sail and gourmet dinner aboard Windfall.

Cast off two hours prior to sunset for a leisurely sail with appetizers, dinner, dessert, and beverages.

Lobster grilled with champaign sauce or choose from our menu

For two:
$475 (Monday - Thursday)
$525 (Friday - Sunday)

Each additional guest:

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

Day Sails

3 hours or less $400
5 hours $600
8 hours $900

Fridays, Saturdays, Sundays, and Holidays: 
3 hours $450 
5 hours $650 
8 hours $950

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)
2 passengers; $1,100 first night
Additional nights $850 per night
Additional passenger $250

Weekend (Friday, Saturday and holidays):
$1250 first night, $1100 second night, double occupancy. Additional passengers are $250 each.

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; $250 per night
Additional passenger; $75 per night
(Five passengers or less)

Weekends (Friday, Saturday and holidays) $275.

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'


sail charters gladly accepts:

We accept Discover, MasterCard, Visa, American Express

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little girl
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Kings of the World
enlarge viewat the winch
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