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.