The Caribbean offers some of the world's best sailing — steady trade winds, short hops between islands, calm anchorages. Here are 7 classic routes:
1. British Virgin Islands (BVI) — beginner's paradise
- Length: 7 days
- Base: Tortola (Road Town, Nanny Cay)
- Highlights: The Baths Virgin Gorda, Soggy Dollar Bar Jost Van Dyke, Anegada lobster lunch, Cooper Island, Norman Island (Pirates of the Caribbean!)
- Why first-timers: short distances (5-15nm), well-marked anchorages, mooring buoys everywhere, English-speaking, easy provisioning. Bareboat or skippered.
2. The Grenadines — Saint Vincent to Grenada
- Length: 10-14 days
- Base: Saint Vincent (Blue Lagoon Marina) or Grenada (Port Louis)
- Highlights: Bequia, Mustique, Canouan, Tobago Cays Marine Park (snorkel turtles), Union Island, Carriacou, Sandy Island Grenada
- Why: less crowded than BVI, dramatic volcanic scenery, Pirates of Caribbean filming locations
3. Leeward Islands — St. Martin to Antigua
- Length: 10-14 days
- Base: Sint Maarten (Simpson Bay Marina) or Antigua (Falmouth Harbour)
- Highlights: Anguilla, St. Barths, Saba (vertical island!), Statia, St. Kitts, Nevis, Barbuda, Antigua
- Why: gourmet stops, history-rich, varied (French chic at St. Barths, Dutch laid-back at Saba)
4. ABC Islands — Aruba/Bonaire/Curaçao
- Length: 7-10 days
- Base: Curaçao (Spanish Water)
- Highlights: Klein Curaçao, Bonaire National Marine Park (world's best shore diving), Aruba's calm leeward coast
- Why: outside hurricane belt, perfect August-October when other Caribbean is risky
5. Bahamas — Exuma Cays
- Length: 10-14 days
- Base: Nassau (Palm Cay) or George Town (Exuma)
- Highlights: Swimming pigs at Big Major Cay, Thunderball Grotto, Iguana Beach, Stocking Island
- Why: shallow turquoise water everywhere, 365 cays to explore, calm anchorages
6. Cuba — South Coast (Trinidad/Cienfuegos)
- Length: 14+ days
- Base: Cienfuegos
- Highlights: Cayo Largo, Jardines de la Reina, Canarreos archipelago, Casilda
- Why: empty anchorages, time capsule, requires careful planning (visa, fees)
7. Saint Lucia/Martinique loop
- Length: 7-10 days
- Base: Saint Lucia (Rodney Bay)
- Highlights: Marigot Bay, Soufrière (Pitons), Anse Mitan Martinique, Sainte-Anne, Les Anses-d'Arlet
- Why: easy passage, French-English contrast, baguettes on the beach
Best season
December–April (15-25 knot trade winds, no rain, no hurricanes). Skipper or bareboat? RYA Day Skipper / ASA 104 minimum for bareboat, otherwise hire skipper (€150-200/day). Cost guide 8-person catamaran in BVI in season: €8,000–15,000/week + provisioning + fuel + mooring fees + skipper. Off-season 30% less.
Companies: The Moorings, Sunsail, Dream Yacht, Horizon, Navigare. Book 9-12 months ahead for peak weeks.