Caribbean sailing has one organising fact and every itinerary obeys it: the trade winds blow from the east, most of the year, most days. Plan a week with that in mind and it is some of the most pleasant sailing anywhere. Plan it without, and the last two days are a beat into wind and swell with a tired crew and a flight to catch.
Go east first, come home downwind
The classic Caribbean week works east while everyone is fresh and returns with the wind behind. In the British Virgin Islands that means starting at the eastern end of the Sir Francis Drake Channel; in the Grenadines it means getting south and east early. Charter bases say this at the briefing, and the crews who ignore it are the ones who arrive back late.
Which island group suits which crew
The BVI: line-of-sight navigation, short hops, moorings in the popular bays, the standard first bareboat. The Grenadines: longer passages, wilder anchorages, more demanding and more rewarding. Antigua and the Leewards: open water and real ocean swell between islands. St Lucia, Martinique and the Windwards: big islands, long legs, and the best actual sailing in the region.
What it costs
The Moorings publishes $3,284 to $49,584 for a 7 day charter for 2 people in the British Virgin Islands, and Sunsail publishes about $3,500 for a low-season bareboat monohull rising to about $10,000 for a high-season four-cabin catamaran. No company in this record publishes a rate for the Grenadines or the Windwards.
Questions people ask about sailing in the caribbean
Which way should a Caribbean itinerary run?
East first while the crew is fresh, returning downwind. The trades blow from the east and a week planned the other way ends in a beat.
Where is best for a first Caribbean charter?
The British Virgin Islands: line-of-sight navigation, short hops, moorings in most popular bays and a large fleet.
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.