The Caribbean is not one destination. It is a string of islands, each with its own weather, customs requirements, provisioning reality, and sailing conditions, spread across 1,500 miles of ocean between Puerto Rico and Grenada. These guides cover four distinct cruising areas: the BVI, where the charter industry is centered and the sailing is designed for success; the Eastern Caribbean arc from Antigua south to Grenada, where going south is fast and going north is work; Puerto Rico, the underrated US-territory base with world-class anchorages; and the US Virgin Islands, the regulatory gateway between American waters and the foreign Caribbean.
All four guides are written from the perspective of the experienced cruiser who wants practical information — what the customs process actually involves, where the provisioning is reliable, what the weather does in the passages between stops — rather than a resort recommendation.
The BVI: The World's Charter Capital
Protected waters, consistent trade winds, short passages, and the circuit from Road Town to Jost Van Dyke that defines Caribbean sailing.
Antigua to Grenada: The Eastern Arc
Eleven islands across 400 miles — English Harbour, the Grenadines, Martinique provisioning, and why the experienced sailor always plans to go south.
Puerto Rico: The Overlooked Base
US territory with no customs hassle, Puerto del Rey (the Caribbean's largest marina), and Culebra's anchorage competing with anything in the BVI.
USVI: St. Thomas, St. John, St. Croix
Three islands with three personalities — the charter hub, the national park, the forgotten one — and the 9-mile gateway to the BVI.
Planning the Caribbean Circuit
The experienced approach to the Caribbean treats the islands as a sequence, not a destination. Fly into San Juan or Charlotte Amalie, provision for the first passage, and plan the circuit south. Going north against the trades is hard; going south with the trades on your beam is one of the best sailing experiences available anywhere.
Puerto Rico and the USVI are US territory — no customs clearance from the US mainland, US cell service, and a regulatory environment that is familiar to American sailors. The BVI is 9 miles east of St. John and requires formal entry. The Eastern Caribbean islands each require their own customs clearance. Budget half a day for customs at each country's first port of entry.
Hurricane season runs June 1 through November 30. The insurance industry treats Grenada and Trinidad as hurricane holes; most of the Caribbean above 12 degrees north is not. Charter companies relocate their fleets south by June 1. Private boats that stay in the Caribbean through hurricane season should be in Grenada or south of it.
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