Overview
Most Caribbean routes run downwind (east to west), making the sailing comfortable but the return trip harder. Plan your circuit to minimize upwind work.
BVI circuit (7 days)
Start from Road Town (Tortola), sail east to Virgin Gorda and The Baths, south to Norman Island and the Bight, north to Jost Van Dyke and the Soggy Dollar Bar, back to Tortola. Passages: 10–25 miles. The Anegada extension adds an extra day.
Grenadines route (10–14 days)
Fly into St. Lucia or Martinique, sail south through St. Vincent, the Tobago Cays, Bequia, and Carriacou to Grenada. More challenging than the BVI — longer passages, stronger trade winds — but deeply rewarding.
Martinique–St Lucia loop (7 days)
Fort-de-France to Soufrière Bay (under the twin Pitons), Rodney Bay, and back to Martinique. French cuisine, volcanic peaks, and good rum throughout.