When the Mediterranean packs up for winter, the Caribbean season begins. From December to April the trade winds blow warm and steady, the water holds 26–28 °C, and two very different cruising grounds compete for your week. The British Virgin Islands are the world's easiest sailing: a ring of islands around the sheltered Sir Francis Drake Channel, every hop line-of-sight and under two hours, a mooring buoy waiting at the end, and a beach bar — the Soggy Dollar, Foxy's, the Willy T — as the evening's institution.
The Windward Islands, from Martinique south through St. Lucia and the Grenadines, are the connoisseur's alternative: French bakeries and Creole markets in Martinique, the Pitons rising straight from the sea in St. Lucia, and the Tobago Cays' horseshoe reef, where you anchor behind coral in water that defies description and turtles graze under the hull. Legs are longer and the open-Atlantic channels between islands blow force 4–6, so it suits crews who genuinely like sailing — or a skippered catamaran.
Catamarans dominate both areas for good reason: shallow drafts for reef anchorages, cockpit living for the climate, and space for the group holidays the Caribbean invites. Book northern-hemisphere summer for the following winter; Christmas–New Year weeks go first.
Sailing conditions
The winter trades blow east-northeast at 15–20 knots with impressive consistency — warm, dependable sailing day after day. December's 'Christmas winds' can gust to 25–30 knots for spells; late spring is gentler. Hurricane season runs June to November: fleets thin out, insurance terms change, and we generally steer charters to December–May. Navigation is reef-aware but straightforward in the BVI; the Grenadines demand more attention to charts and light.
Key marinas & bases
- Nanny Cay & Village Cay (Tortola, BVI)
- Le Marin (Martinique) — the eastern Caribbean's biggest charter base
- Rodney Bay Marina (St. Lucia)
- Blue Lagoon (St. Vincent)
- Scrub Island & Virgin Gorda Yacht Harbour (BVI)
Best time to go
| Period | What to expect |
|---|---|
| December – January | Season opening and festive peak; strongest trades ('Christmas winds'), highest prices around the holidays. |
| February – April | The heart of the season: settled trades, dry weather, every fleet in full swing. |
| May | Gentler winds, emptier anchorages, falling prices — a quietly excellent month. |
| June – November | Hurricane season. Charters possible early on but weather risk grows; most crews wait for December. |
Three routes we recommend
BVI classic loop
Tortola (Road Town) → Norman Island → Cooper Island → Virgin Gorda (The Baths) → Anegada → Jost Van Dyke → Tortola. The world's most forgiving cruising ground, one legendary beach bar per night.
Martinique & St. Lucia taster
Le Marin → Grande Anse d'Arlet → St. Pierre → Rodney Bay → Marigot Bay → the Pitons (Soufrière buoys) → Le Marin. French flavours, rainforest peaks and one proper channel crossing each way.
Grenadines expedition
Le Marin/St. Vincent → Bequia → Mustique → Canouan → Tobago Cays → Mayreau → Union Island → return. Reef anchorages, turtle lagoons and trade-wind passages — the Caribbean at its wildest.
Frequently asked
BVI or the Grenadines?
Do prices differ from the Med?
Is it safe to charter during hurricane season?
Ready to sail here?
See every available boat in this area at official fleet prices — or tell us your dates and we'll shortlist for you.