The Caribbean charter season is the northern winter, which is the first thing to understand about it and the reason its prices move the way they do. While Mediterranean fleets are laid up, the trade winds here are steady, the water is warm and the anchorages are full. Everything about cost follows from that inversion.
What a Caribbean week costs, by island group
The Moorings publishes a 7 day charter for 2 from 2,464 USD in St Lucia, 2,634 in Grenada, 2,974 in Antigua, 3,144 in Belize and 3,284 in the British Virgin Islands, with the same pages running to 64,890, 16,149, 15,999, 29,249 and 49,584 respectively. Conch Charters publishes BVI bareboat monohulls from 2,599 USD a week. Those floors are much closer together than the ceilings, which is the shape of this market.
The season, which is the opposite of the Mediterranean
Peak is mid December to April, with Christmas and New Year the top of every range. The value window is late April to mid July: Conch Charters' rate card puts a four cabin Bali 4.2 at 6,599 USD a week then against 9,599 over the Christmas band. After that comes the hurricane season, when most fleets in the eastern Caribbean reduce or relocate and insurance terms change.
Caribbean sailing trips: which island group for which week
The British Virgin Islands for a first charter: short hops, mooring balls everywhere and no license requirement. The Grenadines for real sailing and emptier anchorages. St Lucia, Martinique and Guadeloupe for longer passages between bigger islands. Antigua for a compact circuit with good harbours. Belize is not really the Caribbean in this sense: it is a reef cruising ground with its own rules and a different kind of week.
What Caribbean sailing cruises add to the bill
Cruising permits and park fees in almost every jurisdiction, mooring balls where anchoring is restricted, fuel and water taken at the bases, and customs clearance if you cross between countries. In the BVI the cruising permit and National Parks Trust moorings are the standard additions. None of it is in the weekly figures above and it is proportionally larger on a cheap boat.
Questions people ask about caribbean sailing vacation
How much is a Caribbean sailing vacation?
The Moorings publishes a 7 day charter for 2 from 2,464 USD in St Lucia, 2,634 in Grenada and 3,284 in the BVI; Conch Charters publishes BVI monohulls from 2,599 a week. All read on 11 September 2026.
When is the Caribbean charter season?
Mid December to April is the peak, with Christmas and New Year at the top of every range. Late April to mid July is the value window before the hurricane season.
Which Caribbean islands are best for a first charter?
The British Virgin Islands: short hops, mooring balls almost everywhere and no national license requirement. The Grenadines suit crews who want real sailing and emptier anchorages.
What extras does a Caribbean charter carry?
Cruising permits and park fees in most jurisdictions, mooring ball charges, fuel and water, and customs clearance when crossing between countries.