Exploring the Caribbean: Best Routes and Hidden Anchorages

The Windward Islands Circuit

The Windward Islands offer the classic Caribbean sailing experience, with reliable trade winds and relatively short passages between islands. This route is perfect for sailors seeking variety and authentic Caribbean culture.

Martinique to St. Lucia (22 nm)

Start your Windward Islands adventure in Martinique’s Le Marin, one of the Caribbean’s premier yacht services centers. The passage to St. Lucia offers excellent sailing conditions, with the dramatic Pitons providing a spectacular welcome to this UNESCO World Heritage island.

Hidden Gem: Anchor in Marigot Bay’s inner lagoon for complete protection and tropical ambiance. The mangrove-lined inlet featured in “Doctor Doolittle” remains unspoiled.

St. Lucia to St. Vincent (21 nm)

The passage to St. Vincent reveals the authentic Caribbean, less developed than its neighbors but rich in natural beauty. The Botanical Gardens are among the oldest in the Western Hemisphere.

Secret Anchorage: Young Island Cut offers protection from swells and access to one of the Caribbean’s most exclusive resorts, yet welcomes visiting yachts to their beach bar.

The Grenadines – Island Hopping Paradise

No Caribbean cruise is complete without exploring the Grenadines. These low-lying islands offer world-class sailing, stunning beaches, and excellent snorkeling in protected marine parks.

• Bequia: Princess Margaret Beach and the charming town of Port Elizabeth
• Mustique: Exclusive island with pristine beaches (day visits welcome)
• Canouan: Magnificent reef system and luxury resort facilities
• Tobago Cays: Marine park with swimming alongside sea turtles
• Union Island: Duty-free shopping and customs clearance

Leeward Islands – Trade Wind Sailing

Antigua to Barbuda (28 nm)

Antigua’s English Harbour offers world-class yacht services and rich maritime history. The passage to Barbuda promises excellent sailing in consistent trade winds.

Hidden Paradise: Barbuda’s Eleven Mile Beach on the windward side offers complete solitude and some of the Caribbean’s most beautiful pink sand beaches.

St. Kitts and Nevis

These sister islands offer dramatic volcanic landscapes and excellent hiking opportunities. Nevis provides a more relaxed atmosphere with beautiful plantation inns.

Secret Spot: Pinney’s Beach on Nevis offers excellent protection and beach access to the Four Seasons Resort facilities.

British Virgin Islands – Sailing Capital

The BVIs represent the pinnacle of Caribbean charter sailing, with short passages, reliable winds, and numerous protected anchorages perfect for sailors of all experience levels.

Classic BVI Circuit

• Tortola Base: Road Town and Nanny Cay marinas
• Norman Island: The Caves snorkeling and Willy T floating bar
• Peter Island: Deadman’s Beach and luxury resort
• Virgin Gorda: The Baths’ unique granite formations
• Anegada: Flat coral island with spectacular reefs
• Jost Van Dyke: Famous beach bars and New Year’s parties

Insider’s Secret: Cooper Island’s Beach Club offers sustainable luxury with solar power, organic gardens, and excellent rum cocktails. The eco-friendly approach makes it a favorite among conscious travelers.

Bahamas – Shallow Water Paradise

Exuma Cays – Swimming Pigs to Iguanas

The Exuma Cays offer unique wildlife encounters and some of the world’s clearest waters. This route requires careful navigation due to shallow depths but rewards with unforgettable experiences.

• Big Major Cay: Swimming with the famous pigs
• Compass Cay: Nurse sharks and stingray encounters
• Iguana Beach: Rock iguanas basking in the sun
• Thunderball Grotto: Underwater cave featured in James Bond films

Abacos – Loyalist Heritage

The Abacos provide excellent sailing conditions with consistent trade winds and protected waters. The colonial settlements offer unique cultural experiences and excellent marina facilities.

Hidden Treasure: Hope Town’s candy-striped lighthouse and colonial architecture create a picture-perfect anchorage. The settlement’s Loyalist history adds cultural depth to natural beauty.

Seasonal Considerations

High Season (December – April)

Perfect weather with consistent trade winds (15-20 knots), minimal rainfall, and comfortable temperatures (75-85°F). This is peak season with higher charter rates and crowded anchorages.

Shoulder Season (May – June, November)

Excellent sailing conditions with fewer crowds and better charter rates. Slightly higher humidity but still very pleasant sailing weather.

Hurricane Season Considerations

July through October brings hurricane risk. While many days offer perfect sailing, this period requires careful weather monitoring and flexible plans. Some areas offer significant discounts but require hurricane insurance.

Navigation and Safety Tips

Coral Reef Navigation

Caribbean waters feature extensive coral reefs requiring careful navigation. Use updated charts, maintain proper lookout, and navigate reef passages only in good light conditions.

Trade Wind Sailing

Consistent northeast trade winds (15-25 knots) create excellent sailing conditions but can build significant seas. Plan passages to take advantage of wind direction and avoid uncomfortable upwind conditions when possible.