The Caribbean season: timeline, ports and how it differs from the Med

The other half of the yachting year, and a genuinely different job. THE CALENDAR • October–November: crossings from the Med, or boats coming down from the US East Coast. Fort Lauderdale is the hiring hub. • December–January: peak. Christmas and New Year charters are the most valuable and most demanding weeks of the season anywhere. • February–April: steady charter, then boats start heading north or back across. • Hurricane season roughly June to November dictates the whole shape of it. WHERE Antigua, St Barths, St Maarten/Sint Maarten, the BVI, the Grenadines, and increasingly the Bahamas as a separate circuit. St Maarten is the practical hub for parts and yard work. HOW IT DIFFERS FROM THE MED Longer passages between islands and more actual sea time. More time at anchor and less stern-to. Much heavier watersports and toys programme. Provisioning is harder and more expensive, so galley and interior planning matters far more. And a slower, warmer social culture on the dock. THE THINGS PEOPLE UNDERESTIMATE Getting spares to an island. Weather that genuinely changes plans. Sun exposure over months of open-water work. And that a New Year charter can be the hardest fortnight of your working life. VISAS If any part of the plan touches US waters, sort the B1/B2 early — see the Visas section. It's the most common reason people miss the season. Done a Caribbean season? What do you wish you'd packed, or known?