Shipping costs: UPS and FEDEX charge between $350 and $480 for a 12/btl shipment to St. Thomas.

Paperwork:  Common carriers regard the US Virgin Islands as an international destination and this requires additional paperwork which would not be required from a club member living in the 50 states.

Hassle: Most wineries use a fulfillment company to handle and ship all of their wine club shipments.  It’s not financially viable for them to make an exception to include shipments to a tiny US territory.

Shipping costs: Same concerns as the wineries.

Quality Control: If a consumer were to ship via common carrier there would be no guarantee as to the temperature controls under which their wine would be transported.

Hassle: Unfortunately, asking a winery to send wine club shipments to you in the Caribbean is similar to asking them to send you wine to the Sahara.  Demand is low and so are their margins.