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Destinations
Caribbean sailing guide 2025 – BVI to Windwards island hopping
January 6, 202511 min
The Caribbean delivers trade‑wind passages, palm‑lined anchorages and line‑of‑sight navigation for all levels.
Why sail the Caribbean
- Consistent NE trades, warm water year‑round.
- Easy pilotage in the BVI; adventurous hops in the Windwards.
- Excellent charter infrastructure.
Season & weather
| Period | Notes |
|---|---|
| Dec–Apr | Peak season, stable trades |
| May–Jun | Shoulder, good value |
| Jul–Nov | Hurricane season; monitor forecasts and insurance requirements |
7‑day BVI itinerary
Tortola – Norman – Cooper – Virgin Gorda – Anegada – Jost Van Dyke – Tortola.
Windwards (7–10 days)
St Vincent – Bequia – Tobago Cays – Mayreau – Union – Carriacou – Grenada.
Clearance & practical tips
Carry passports for inter‑island formalities; check local mooring regulations; secure hurricane clauses if sailing Jul–Nov.
Charterwerk tips
Choose catamarans for shallow sandbars; plan upwind legs early; leverage our best price guarantee.