Complete Guide to Caribbean Cruising for Sailors

Cruising the Caribbean is a dream for many sailors. The warm trade winds, crystal clear waters, and island-hopping adventures draw thousands of boats each winter season. This comprehensive guide covers everything you need to know to plan and execute your Caribbean sailing adventure.

Planning Your Route

The Caribbean offers multiple cruising grounds, each with its own character. The Eastern Caribbean chain stretches from the Virgin Islands south through the Windward and Leeward Islands to Trinidad. This is the classic trade wind route, with consistent 15-20 knot easterlies making passages predictable.

The Western Caribbean includes Belize, the Bay Islands of Honduras, and the coast of Mexico. This area offers more protected waters and fascinating Mayan ruins, but requires more careful weather watching due to the influence of fronts from the Gulf of Mexico.

Most cruisers start in the Virgin Islands, either USVI or BVI. St. Thomas has excellent provisioning and flight connections. The BVI offers more anchoring options and a more relaxed atmosphere. From here, the traditional route runs south through St. Martin, Guadeloupe, Dominica, Martinique, St. Lucia, and down to Grenada.

Timing and Seasons

Hurricane season officially runs June 1 through November 30. Most cruisers arrive in November or December and head south by May. Trinidad and Grenada lie south of the traditional hurricane belt and offer haul-out facilities for boats staying through summer.

The Christmas winds bring strong trades in December and January – often 25+ knots. January through April sees more moderate 15-20 knot trades. May can be light and unsettled as the weather pattern transitions.

North swells from Atlantic storms can make northern anchorages uncomfortable even in fair weather. Check swell forecasts before anchoring on north-facing shores.

Boat Preparation

Your boat needs to be self-sufficient for extended cruising. Parts and services vary widely by island, and what’s available in St. Martin may be impossible to find in Dominica.

Carry comprehensive spares for all critical systems: impellers, belts, hoses, fuel filters, oil filters, zincs, and electrical components. Having the right spare when you need it can save a week waiting for shipment.

Watermakers become almost essential for extended Caribbean cruising. Water is scarce and expensive on many islands. A modest watermaker producing 10-15 gallons per hour keeps tanks full without constant shore visits.

Solar panels and wind generators reduce dependence on your engine for charging. The strong trade winds make wind generators particularly effective. Combine with a good battery bank and you may rarely run your engine for charging alone.

Refrigeration is a major power consumer but makes life much more comfortable. Plan your electrical system carefully to support it.

Navigation and Charts

Modern chart plotters cover the Caribbean well, but carry paper charts as backup. Electronic chart coverage varies – some areas have excellent detail while others rely on surveys from the colonial era.

Use your eyes as your primary navigation tool. The clear water makes visual navigation practical and often more accurate than electronic charts. Learn to read water colors: dark blue is deep, lighter blue is shallower, brown means coral heads.

The Pavlidis guides remain the most comprehensive cruising references for the Eastern Caribbean. Street’s guides are older but contain valuable local knowledge. Supplement with Cruisers’ Net reports and advice from fellow cruisers.

Anchoring Techniques

Caribbean anchoring presents unique challenges. The holding varies dramatically from island to island and bay to bay. Sand is generally good holding, but the grassy patches common throughout the region can defeat many anchor designs.

A properly sized anchor is essential. For most cruising boats, this means 45-60 pounds of CQR, Delta, or modern designs like the Rocna or Mantus. Carry a backup anchor of a different design for challenging bottoms.

Scope requirements vary with conditions. In the protected anchorages of the Virgins, 5:1 scope is usually adequate. In more exposed anchorages or during Christmas winds, 7:1 or more provides necessary security.

Set your anchor with a good backing down and verify it’s holding before settling in. Re-check after any significant wind shift. Many boats drag anchor each season because of inadequate setting.

Customs and Immigration

Each island nation has its own entry requirements. Plan to clear customs at your first port of entry in each country. Most islands have designated ports of entry – arriving elsewhere can result in fines.

Carry your boat documentation, crew lists, passports, and clearance from your previous port. Some islands require advance notification through services like eSeaClear or NOONSITE.

Fees vary widely. Some islands are essentially free, while others charge significant clearance fees. Budget accordingly and carry US dollars – they’re accepted almost everywhere, though change may come in local currency.

Provisioning Strategies

Provisioning quality and selection varies dramatically by island. The French islands – St. Martin, Guadeloupe, Martinique – offer superb French provisions at reasonable prices. The BVI and USVI have good American-style supermarkets at American prices.

Stock up on favorites when you find them. That special hot sauce or your preferred coffee may not appear again for weeks. Fresh produce availability fluctuates with cargo ship schedules.

Local markets offer the best deals on produce, especially on less-developed islands. Arrive early for the best selection. Local fruits like papaya, mango, and coconut are abundant in season.

Health and Safety

Medical care varies from excellent to non-existent. St. Martin, Martinique, and Puerto Rico have modern hospitals. Remote islands may have only a nurse or nothing at all.

Carry a comprehensive first aid kit and know how to use it. Include prescription antibiotics for common problems. Consider taking a wilderness first aid course before departing.

Theft is a reality in some areas. Research current conditions before visiting each island. Lock your dinghy, don’t leave valuables visible, and follow local advice about safety ashore.

Making the Most of Your Cruise

The Caribbean offers far more than just sailing. Each island has its own culture, cuisine, and character. Take time to explore ashore, hike the trails, visit the historic sites, and engage with local communities.

The cruising community provides companionship and support. VHF nets operate on most islands – check in daily to hear weather, announcements, and connect with other cruisers.

Don’t rush. The temptation is to cover as much territory as possible, but the best Caribbean experiences come from lingering in places that speak to you.

Conclusion

Caribbean cruising rewards preparation and flexibility. Come with a seaworthy boat, an open schedule, and a spirit of adventure. The challenges are manageable and the rewards immense. Start planning your Caribbean adventure today.