Sailing the Caribbean means choosing an island group, because they are not variations on a theme. The British Virgin Islands are a protected ring you can see across; the Grenadines are strung out with real passages; St Lucia and Martinique are big islands with long legs between them. The trade winds run east, and that fact organises every itinerary in the region.
The island groups, and how hard each week is
The BVI: line-of-sight navigation, short hops, moorings in most bays, the standard first charter. The Grenadines: longer passages, wilder anchorages, more rewarding and more demanding. Antigua and the Leewards: open water between islands and real ocean swell. St Lucia, Martinique and the Windwards: big islands, long legs, and the best chance of sailing rather than motoring.
What it costs, on the two companies that publish
The Moorings publishes $3,284 to $49,584 for a 7 day charter for 2 people in the British Virgin Islands. Sunsail publishes about $3,500 for a low-season bareboat monohull and about $5,700 for a low-season catamaran, rising to around $7,000 and about $10,000 in high season. No company in this record publishes a rate for the Grenadines or the Windwards.
Plan the week downwind, then back
The trades blow from the east most of the year, so the classic Caribbean week goes east first while everyone is fresh and comes home with the wind behind. Plan it the other way and the last two days are a beat into wind and swell with a tired crew. Charter bases will tell you this on the briefing; it is worth building the itinerary around it before you arrive.
Questions people ask about sailing the caribbean
Where is best for sailing in the Caribbean?
The BVI for a first or easy week, the Grenadines for more demanding cruising, the Windwards for the best actual sailing. They are quite different weeks.
How much does Caribbean sailing cost?
The Moorings publishes $3,284 to $49,584 for a 7 day BVI charter for 2 people; Sunsail publishes about $3,500 low season for a bareboat monohull rising to about $10,000 for a high-season catamaran.
Which way should a Caribbean itinerary run?
East first, with the return downwind. The trades blow from the east and a week planned the other way ends in a beat with a tired crew.