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 Captain Mark and First and Only Mate, Suzanne Invite you

to Join us for a Vacation of a Lifetime 


Ahoy Crew! Have you ever dreamed of island hopping in the Caribbean aboard a beautiful sailing yacht? Start planning your dream vaction NOW aboard Island Girl, an amazingly spacious, comfortable and seaworthy vessel!























Please take the time to check out the photos and descriptions that will be appearing on this new website -  We will be updating on a regular basis and will begin taking reservations for the 2021-22 season in the near future.

These sailing adventures are available on a very limited first come basis.  If you are interested in learning more or making a tentative reservation without any obligation to commit at this time, then please send us an email to let us know. We will place you on a special email list updating you with all the details and giving you the earliest opportunity to confirm a reservation.

Please do your research by reading up on the cruising grounds, learning more about us through our Blue Crab website and reading the reviews we have received on Trip Advisor.

We are looking forward to sailing with you in the beautiful Caribbean aboard ISLAND GIRL

Smooth Sailin'

Capt. Mark and First and Only Mate Suzanne



Blue Crab Chesapeake Charters offers FIVE day - FIVE island sailing cruises in the US and British Virgin Islands aboard Island Girl.  Very limited in availability, and at unbeatable prices, these cruise vacations typically sell out in less than a month upon being announced. The sailing adventures are offered exclusively to our guests who have sailed with us on the Chesapeake Bay and are limited to just one couple at a time as a completely private Caribbean adventure. By booking early, each couple is able to plan, save up their cruising kitties, research the fabulous cruising grounds of the US and British Virgin Islands and anticipate the excitement of an adventure of a lifetime - Island hopping in the Caribbean.    

In preparation for every sailing vacation, we consult with each couple, discussing itineraries and other important details about their vacation. The end result is a completely individualized opportunity for superb sailing, idyllic weather, exploration, discovery, priceless camaraderie and memories that last forever. To this day, most of our Caribbean guests return, some, each year, to sail with us on the Chesapeake Bay.  

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