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.

Gloucester scenes

Depending on the duration of your charter, you will be served complimentary morning fruit, freshly baked goods, or light hors d’oeuvres and beverages including:

  • juices
  • soft drinks
  • coffee/tea
  • “house” beer and wine

Lunch and/or dinner on board 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.
Minimum three-hour day sails may be extended by one hour increments to your desired cruise time.

Day Sail Rates

Overnight Sail

(Does not necessarily mean being underway throughout the night)

One night (10:00 am–2:00 pm the following day; approximate times) is the minimum reservation. Additional nights and additional passengers (up to four passengers) are more than welcome.

Your all-inclusive Overnight Sail consists of:

  • breakfast, lunch
  • hors d’oeuvre
  • dinner, dessert and beverages including:
    • juices
    • soft drinks
    • coffee/tea
    • “house” beer and wine

Have a look at our Sample Menus.

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

Overnight Sail Rates

B&B (Boat and Breakfast) Dockside in Gloucester

Your private vessel for the evening, Windfall remains docked at Beacon Marine Basin in Smith’s Cove within walking distance to the famed Rocky Neck Artist Colony.

Upon your 4-5 pm arrival you will be greeted with chilled, sparkling wine and hors d’oeuvre. In the morning enjoy a leisurely breakfast of freshly baked goods, seasonal fruit, juice and coffee/tea before your 10 am departure.

Additional nights and additional passengers (up to five) are more than welcome.

B&B Dockside Rates

Romantic Sail and Dinner

Celebrate sunset and/or your special occasion with a three-hour sail and a specially prepared gourmet dinner.

Cast off two hours prior to sunset for a leisurely sail with hors d’oeuvre, dinner, dessert and beverages (soft drinks, “house” beer and/or wine) served on historic Gloucester Harbor.

May we suggest Grilled Lobster with Champagne Sauce or choose your specially prepared gourmet meal from our Sample Menus.

Romantic Sail and Dinner Rates

Romantic Get-Away with B&B Dockside

Celebrate your special occasion with a three-hour sail, gourmet dinner and private B&B dockside aboard Windfall.

Cast off two hours prior to sunset for a leisurely sail. You will be greeted with chilled sparkling wine and hors d’oeuvre while getting underway. Your exclusively prepared dinner and dessert will be served at sunset on historic Gloucester Harbor.

Choose from our Sample Menus for your specially prepared gourmet meal.

After dinner Windfall will return to her berth at Beacon Marin Basin where you will enjoy the remainder of your romantic evening alone dockside.

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

Romantic Get-Away Rates

Create Your Own Reason to Sail, Sail, Sail!

  • Sail into sunset
  • Sail before or after your B&B
  • Sail and shop in Rockport (no traffic or parking worries!)
  • Sail and picnic ashore
  • Sail to sharpen your sailing skills
  • Sail to fish…Yes, you can fish from a sailing vessel! “No fuss, no muss”; the Captain does the filleting! Bringing your personal fishing gear is encouraged.

Contact Captain Raffi for ideas and rates for Create Your Own Reason to Sail! or with any questions concerning; itinerary or destination suggestions, dietary concerns, additional hours, days, nights or passengers at; 978-948-5434 or

defiance sail charters gladly accepts:

Discover, MasterCard, Visa, American Express

dinner in the main cabin
lobsters on deck
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cockpit - ship/crew page
Madame Captain - rates page
Roses - rates page
Bahamas Girl - rates page
interior shot - ship/crew page
interior shot-forward berth -ship/crew page
interior shot-saloon - ship/crew page
sailing by the Statue of Liberty -ship/crew page
sunset over the winch - ship/crew page
Captains Lisa and Raffi - ship/crew page
sailing by Eastern Point - local info page
Windfall in the Bahamas-contact page
Windfall under sail - rates page
sailing in New England
group on the bow
Raffi teaching the kids
Happy Gals
little girl
Girls jumping into the water
windfall under sail
Gloucester Harbor Paint Factory
Gloucester Fisherman Statue