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Winter Season
The British Virgin Islands - The B.V.I.
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Check Out our New Video! By Clicking on the Image to the left.

Winter Season: November to the end of March
Please call or email us to book a Charter
Phone: (781) 591-9783
Captain.Chris@DuchessOfBoston.com

Chartering your own Sail Boat is cheaper then most Waterfront Hotels & Resorts
British Virgin Islands (BVI)

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- 5% Discount on the Boat from the Moorings since Captain Chris is a repeat Charterer.
- Sail in November and early December.  Monohulls can be up to 20% less and Catamarans can be up to 40% less.

For a complete
Tropical Getaway
the BVI is it!



Marina, Cay, BVI

  • 4 hour Non-Stop flight from Boston to Saint Thomas with a 1 hour ferry ride to Tortola
  • Rejuvenate Your Mind and Body!
  • The rhythm of Your days is taken over by the warmth of the Sun, refreshing breezes as You sail to the next Harbor and numerous dips in the water to cool off
  • Plenty of Waterfront Restaurants for Dining & Entertainment
  • The natural beauty of these Mountainous Isolated Islands continually takes Your breath away

Winter Season

  • Captain Fee rate of $220/day this includes Captain's food and travel to BVI and Florida location
  • 5% Discount on the Boat from the Moorings since Captain Chris is a repeat Charterer.
  • Boat prices vary depending on location, Boat size and travel dates
  • Call Captain Chris to discuss the details

Why choose Captain Chris?

  • If you sailed with Captain Chris in Boston Harbor and enjoyed the Sailing Experience without the pressure this is the vacation for you!
  • Captain Chris is on duty Day & Night!
  • Captain Chris doesn't require his own Cabin. 
  • Relax and do as much or as little as you want
  • Learn the basics of Sailing one day and relax the next
  • All Charters are customized for You
  • You can't force a Sailing Vacation.  You need to just go where the Wind and Weather provide the most enjoyment


Captain Chris
on the
40ft Leopard Catamaran

How it Works

  • Sail Boat is Chartered from the Moorings.  Captain Chris selected the Moorings since all Sail Boats are less than 5 years old.  A New Sail Boat adds to the enjoyment of the Charter by reducing the risk of equipment malfunction.
  • Sail Boat Prices can be viewed at MOORINGS.COM
  • Maximum of 6 people
  • Minimum of 5 days
  • Payment made to The Moorings for the Sail Boat
  • Payment made to Duchess of Boston Sailing Charters, LLC for the Captain Fees