The Caribbean is not one charter market but six or seven, and the difference between them is a factor of two before a single extra is added. The Moorings prints a seven day starting price on every destination page it runs, which makes the islands directly comparable for once, and the ranking that falls out of those figures is not the ranking most people expect.
Caribbean yacht charter prices, island by island
Read on 11 September 2026, The Moorings prices a seven day charter for two from 2,464 USD in St Lucia, 2,634 in Grenada, 2,974 in Antigua, 3,144 in Belize, 3,284 in the British Virgin Islands, 4,199 in St Martin, 4,529 in the Exumas and 5,579 in the Abacos. The cheapest entry in the Caribbean is therefore the Windwards, not the BVI, and the Bahamas is the most expensive water in the region to start a bareboat week in.
Caribbean sailboat charter: bareboat, skippered and crewed
The same pages split the ladder. In St Lucia bareboat runs 2,464 to 9,714, a skipper added to a bareboat is 240 a night, and a fully crewed yacht runs 13,949 to 64,890. In the BVI bareboat starts at 3,284, a skipper is 330 a night, the skippered package runs 6,284 to 24,834 and crewed runs 13,134 to 49,584. A skipper is the cheapest upgrade in the trade: seven nights of one costs less than the gap between a small monohull and a mid catamaran.
What the trade wind does to the sailing trips Caribbean crews take
The trade wind blows from the east at fifteen to twenty knots almost every day of the season, so the whole region sails across or downwind on the outward leg and works back against it. The BVI does this inside a sheltered channel with twenty mile days. The Windwards, from St Lucia south through the Grenadines to Grenada, are open passages of twenty to thirty miles between islands with real swell in the channels. The Bahamas is shallow, flat and tidal, and the constraint there is draught rather than wind.
What the published figure leaves out
The Moorings states additional costs separately and they are large: around 1,800 USD for two people on a BVI week, 1,600 in St Lucia and Antigua, 1,400 in St Martin and 1,200 in Grenada and Belize. On its BVI page it itemises flights at roughly 500 to 1,300 per person return and a shared taxi transfer at about 18 per person. Provisioning, fuel, cruising permits and mooring balls sit inside those figures, and none of them appear in the headline price.
Questions people ask about sailing charters caribbean
Which Caribbean island is cheapest to charter from?
Of the bases publishing a figure, St Lucia at 2,464 USD for a seven day charter for two, then Grenada at 2,634 and Antigua at 2,974, all read from The Moorings on 11 September 2026.
How much does a skipper add?
The Moorings charges 240 a night in St Lucia, 310 in St Martin, 330 in the BVI, 345 in the Exumas and 190 in Belize, all added to the bareboat price rather than replacing it.
When is the Caribbean sailing season?
December to April is the settled trade wind season and carries the highest prices, with Christmas and New Year at the top of every range. Late April to mid July is the value window before the hurricane season closes most fleets.
How much is a Caribbean crewed yacht charter?
The Moorings prices a fully crewed yacht at 13,949 to 64,890 USD in St Lucia and 13,134 to 49,584 in the British Virgin Islands for a seven day charter for two, read on 11 September 2026.