Saint John occupies the eastern end of the US Virgin Islands, separated from the British Virgin Islands by the narrow Pillsbury Sound. A sailing charter beginning here has access to two distinct sailing grounds: the USVI’s protected bays and national park beaches to the west, and the trade-wind circuit of the BVI to the east. The daily choice between these two worlds, made over breakfast in Cruz Bay or Coral Bay, defines the character of a Saint John sailing week.
The crewed sailing charter fleet available in the USVI numbers around 19 published yachts. These are vessels comfortable with the 10-mile crossing to the BVI and the longer passages south toward Saint Croix. A sailing yacht based at Saint John can anchor at the Bight on Norman Island on day one, beat to windward toward Virgin Gorda on day two, and return to the USVI on day five for a final anchorage at Waterlemon Cay before the charter ends.
Weekly sailing charter rates in the USVI start at approximately 50,000 euros for a 25-metre sloop and reach 120,000 euros for a larger performance sailing yacht. The advance provisioning allowance of 30 percent covers fuel for engine-assisted passages, provisioning and the modest USVI customs fees. The northeast trade winds are at their most reliable from January through April, and sailing conditions in Pillsbury Sound and the Drake Channel are generally excellent across the peak season.
The passage from Cruz Bay east into the BVI takes two to three hours under sail, crossing through Pillsbury Sound with a consistent 15-knot beam reach and arriving at Norman Island or Peter Island in time for a first lunch at anchor. The return passage is a beat to windward that takes longer but delivers the kind of active sailing that motivates guests to book a sailing yacht rather than a motor vessel.
