What Actually Makes the Windward Islands Different FromSailing
The Windward Islands sit at the eastern entrance to the Caribbean, which means they take the full force of the Atlantic before anything reaches the calmer Leeward Islands. That makes them one of the more exposed sailing areas in the region. The trade winds blow steadily out of the east-northeast, currents run fast through the passages, and some of the channels have cross-channels that will shove you sideways if you don't account for them properly. I've done this route maybe a dozen times across two decades, and the things that trip people up are always the same. Underestimating the tidal streams. Reading charts that aren't current. And not having a plan for what happens when the wind dies or hits 35 knots in a narrow passage with no escape.
The Sailors Guide To The Windward Islands
There isn't one single authoritative book called "The Sailors Guide To The Windward Islands." What exists is a collection of cruising guides, passage guides, and local knowledge that sailors piece together. The most commonly referenced materials are the British Admiralty charts (NP series), the United States Nautical Chart volumes, Jean-Yves Leroux's Windward Islands Cruising Guide, and the various online forums and tidal stream databases that experienced cruisers maintain. If you're looking for something downloadable, the Scribe Digital Cruising Guide for the Eastern Caribbean covers the Windwards quite thoroughly, and the NOAA charts are freely available online. This is the most commonly sailed crossing in the Windwards. It's roughly 40 nautical miles, usually takes 6 to 9 hours depending on your boat and the wind angle. The tricky part isn't the distance. It's the current. The Grenada Canal runs between the two islands, and the tidal stream there can hit 3 to 4 knots. If you time your departure wrong, you're fighting a headcurrent the entire way, which turns a comfortable sail into something that feels much longer. I learned this the hard way on my second crossing. Left Grenada at mid-morning thinking the current would be neutral. It wasn't. I was making 3 knots over ground instead of 6, the wind had dropped to 8 knots by early afternoon, and I was motoring the last 20 miles through a sea state that kept getting worse. Took 14 hours total. Since then I time departures around slack water, which you can find in the tide tables for the Grenada Canal. The window is usually about 2 hours either side of high water at St. George's, Grenada.
Reading the Channels
The Windward Islands have some deceptively narrow passages. The Soufrière Strait between Martinique and St. Lucia is probably the most famous. It's well charted now, but even with modern electronics, the current through there can exceed 5 knots at certain stages of the tide. I've seen boats drift into the channel center and make zero forward progress against it. The key insight that most guidebooks don't emphasize enough: the current direction and strength in these passages doesn't follow the standard tidal curve you'd expect from a single port's tide table. The Grenada Canal, the Soufrière Strait, and the passages around Dominica all have their own localized tidal behavior. The Admiralty Tide Tables (ATT) Volume 5 covers the Caribbean and has the detailed predictions, but even those are approximations. The most reliable approach is to check the real-time current reports from marinas and talking to other boats when you arrive. A quick question at the dock in Grenada about current conditions will save you a lot of trouble compared to relying solely on published tables.
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Weather Windows and the ITCZ
Between June and November you're in hurricane season, which is obvious but worth restating. The less obvious part is the Intertropical Convergence Zone, or ITCZ. When it settles over the Windwards, you can get days of light and variable winds, heavy thunderstorms, and visibility down to a few hundred meters. This usually happens in August and September. If you're planning to motor-sail through the channels during this period, make sure your engine is reliable and you have fuel to spare. The wind won't always help you. December through April is the dry season and generally the best sailing weather. Trades are steady at 15 to 20 knots, seas are manageable, and the skies are clear. This is also peak season, which means marinas are fuller and fuel prices can be higher. Not a bad trade-off.
Specific Problem: The Dominica Approach
Approaching Dominica from the south through the Morne Rouge Passage is where I ran into my most memorable issue. The approach chart showed a drying rock just off the main channel, marked as a hazard. I was running on my plotter, which was displaying the latest ENC data. Halfway through the passage, the plotter lost GPS signal for about 90 seconds — apparently interference from the surrounding mountains, which is common in Dominica. When it came back, my position jumped by about 200 meters. I didn't know if I was closer to that drying rock or further away. The workaround was simple but not obvious if you haven't dealt with it: I reduced speed immediately, switched to visual navigation using the transits shown on the chart (two fixed points aligned when you're on the safe channel), and called ahead to Roseau Marine to confirm current conditions. They told me the rock was covered at the time, but I still kept the boat under engine power and moved slowly until I was well clear. The transits are your safety net when electronics fail. Learn them before you need them.
Common Pitfalls
Here are the things I see repeated, year after year: Neglecting to check fuel range against current conditions. A boat that normally does 6 knots on sail might be doing 3 knots under power if the current is against you. That doubles your fuel consumption for the passage. Always calculate worst case, not best case. Underestimating the sea state inside the channels. The open ocean might be flat, but once you enter a narrow channel with strong current running against the wind, the chop becomes steep and uncomfortable very quickly. This is especially true in the Grenada Canal and around the north coast of St. Lucia. Plan for a rougher ride than the weather forecast suggests.
Not having alternate anchorages. Some of the Windward Islands have very few protected anchorages. St. Vincent's Kingstown Harbour can be crowded and exposed to swell from the east. If you're arriving late and the harbour master is gone, you might end up anchoring outside with no shelter. Know your backup options before you need them.
Essential Resources
The British Admiralty chart series for the eastern Caribbean is still the gold standard for detail and accuracy. The relevant charts are NP10 (Windward Islands general), NP766 (Grenada to St. Vincent), and NP767 (Martinique and St. Lucia). If you prefer electronic charts, SeaPro and Navionics both cover the area, but always cross-reference with the paper charts, especially for the shallow passages. The Cruising Guide to the Windward Islands by David Mullholland is still in print and covers many of the anchorages and harbours in detail. It's not as comprehensive as some of the newer digital guides, but the anchorages it describes haven't changed, and the written descriptions of approach hazards are still accurate. For real-time information, the Facebook group "Eastern Caribbean Cruisers" is actually useful. It's maintained by sailors who are currently in the region, and people post current conditions, harbour masters' phone numbers, and fuel prices regularly. It's not a substitute for proper planning, but it's better than arriving somewhere and having no idea what the situation is.
What These Guides Don't Tell You
The biggest gap in most published sailing guides for the Windward Islands is the lack of honest discussion about the costs and the crowds. Popular anchorages like Picard Beach in St. Lucia or Prickly Pear in Grenada fill up quickly during December and January. There's often no room for late arrivals. You end up anchoring further out and dealing with a dinghy ride to shore, which is fine for one night but exhausting if you're stuck there for a week. Another thing that isn't emphasized enough: customs and immigration procedures vary significantly between islands. Grenada is straightforward. Dominica can take several hours if you arrive after office hours and need to arrange a special clearance. St. Lucia has started using online pre-clearance for some visits, which saves time if you plan ahead. Check the requirements before you sail. The last thing you want is to be anchored outside a harbour on a Saturday evening with no way to clear in before Monday morning. The Windward Islands are one of the most rewarding sailing areas in the Caribbean if you respect the conditions. The passages are challenging but not dangerous. The anchorages are beautiful. The culture is rich. Just make sure you've done your homework on currents, weather, and fuel before you commit to any crossing. A well-planned passage through these islands is one of the best experiences you'll have on the water. A poorly planned one will test your patience and your boat's systems in equal measure.
