British Virgin Islands & Leewards
Caribbean Yacht Charter
Short passages, protected anchorages and reliable trade winds — the classic catamaran cruising ground.
Season December – April
Chartering in the Caribbean
The Caribbean season runs December to April, defined by the trade winds and the hurricane calendar. The trades blow steadily from the east-north-east at 15 to 20 knots, which makes for the most reliable sailing conditions anywhere in the world.
The British Virgin Islands is where most people take their first catamaran week, and rightly so. The Sir Francis Drake Channel is protected on both sides, the hops between anchorages are two hours rather than two days, and there is somewhere to be every evening. Further south in the Grenadines the passages are longer and more open — better sailing, but not a first week.
The value window is late April to mid-May: the water is at its warmest, hurricane season is still weeks off, and the fleet is discounting before repositioning. Christmas and New Year is the opposite — book a year ahead and expect to pay roughly double.
Common questions
- When is hurricane season in the Caribbean?
- Officially June to November, with mid-August to October the highest risk. Most charter operations move south of the hurricane belt or shut down during those months.
- Is a catamaran better than a monohull in the Caribbean?
- For most charter parties, yes. Shallow draft opens up more anchorages, the boat does not heel under sail and it barely rolls at anchor — which matters if anyone aboard is prone to seasickness.
The fleet