ISLAND SKIPPER is a fully crewed charter yacht operating in the US and British Virgin Islands.  Our sailing grounds include St. John, Anegada, and the protected waters of the Sir Francis Drake Channel with sunny days, fresh trade winds, calm anchorages and a comfortable daytime temperature of about 82 degrees. 

Sailing the Virgin Islands on your own private yacht is a refreshing, laid back experience which allows you to do what you like to do. 

The Captain & Crew can take care of sailing the yacht for you or help you develop the confidence to sail it yourself. It’s your choice. You can take a turn at the helm, lend a hand trimming a sheet, or just sit back and enjoy the ride. 

If you want to snorkel, fish, dive, kayak & hike- that's fine.  Or you may prefer to lay in the hammock, read and sip boat drinks - that's fine too.  But be warned, the fresh breezes of the trade winds and the crystal blue waters are addicting and you may never want to go back home. 

We cater to groups of all ages from 6 to 84. Our sailing yacht is ideally suited for one couple who wants privacy, two couples (each with their own bathroom) or a family of up to six.  If there are more people in your party, a tandem charter with ISLAND SKIPPER and a second yacht can be arranged. 

So come aboard and sail with us for a week or two of tropical breezes, lots of adventures, candle lit dinners and frozen boat drinks. As the owners and operators of ISLAND SKIPPER, it is our goal to make your stay aboard ISLAND SKIPPER your most memorable vacation ever.

If you are not familiar with this type of vacation, click here for an explanation.