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Sailing the East Caribbean requires understanding the distinction between windward and leeward routes, as well as the seasonal weather patterns that dictate cruising safety. The primary cruising season runs from December 1 to June 1, when weather is most stable; the hurricane season, peaking between mid-August and late September, necessitates staying south of St. Vincent.15:13 When sailing north from Grenada toward St. Martin, the leeward (west) side of islands offers protection from ocean swells and provides the majority of anchorages, though it often lacks consistent wind.14:16 The windward (east) side provides more consistent wind but requires navigating reef areas and dealing with rougher seas.13:21

Arrival procedures in St. Martin involve checking in at Marigot on the French side, which is generally cheaper than the Dutch side.2:29 In Grenada, customs clearance is available at Carriacou Marine or Port Louis Marina in St. George’s.7:54 Using the SailClear website before arrival streamlines the immigration and customs process.1:43:34 Essential marine infrastructure, including Island Waterworld and Budget Marine, is concentrated in St. Martin and Grenada to facilitate repairs and provisioning.6:26

Understanding seasonal wind shifts and island geography allows for safer, more comfortable passages.

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