The Lovely Leeward Islands: Something for Everyone

For superb sailing and sensational shoreside attractions, a spin around St. Maarten, Anguilla and St. Barts is hard to beat.

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A row of superyachts line the pier in the protected harbor of Gustavia on the island of St. Barts. The gorgeous French island is synonymous with the very best of everything.Bobby Grieser/Outside Images

There are bustling cafes for strong coffee and flaky croissants, where the background conversation has a decidedly French accent. Or perhaps you’d prefer miles of pristine white sand beaches, many of which you have all to yourself. Then again, if what you’re after is champagne sailing across turquoise seas flecked with whitecaps, well, that’s most certainly an option. That’s one of the best things about a charter cruise of the northernmost Leeward Islands: Whatever you desire, you’ll find it!

Dutch? French? Charters generally originate on the truly international (and somewhat schizophrenic) island of St. Maarten, half of which is French, the other Dutch. You can spend the ­morning enjoying cafe society on the northern, French side in Marigot, and the afternoon strolling down the beachside walkway fronting the many bars and restaurants on the southern, Dutch side in Philipsburg. Or, of course, you could take in both scenes from the comfort of your cockpit, as each city is located adjacent to a protected anchorage, the former by Marigot Bay and the latter off Great Bay.

In recent years, St. Maarten has gone through a boom period (which accounts for the many cruise ships in Great Bay and the row of superyachts docked in the Simpson Bay Lagoon). However, there are also enough anchorages and marinas that you could spend a delightful week circum­navigating the island and enjoy a different destination every night. But then you’d miss the isle’s alluring neighbors.

Laid-Back Anguilla

Across Anguilla Channel from St. Maarten lies the low, friendly island of Anguilla. On a windy day, you can cover the roughly 12 nautical miles from Marigot to Road Bay, Anguilla’s most popular anchorage, in just a couple of boisterous hours. But while the relative distance is short, in some aspects you’re a world away.

Anguilla may be what St. Maarten was like before it became, well, St. Maarten. The vibe is mellow, the high-rise hotels nonexistent. What Anguilla lacks in glitz is more than made up for by the place’s astounding natural beauty: Surrounded by coral reefs and graced with numerous gorgeous beaches, it’s the very embodiment of what has attracted sailors to the Caribbean for centuries.

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A couple of things you’ll see a lot of on Anguilla: sandy beaches like this one on Road Bay, and goats.Bobby Grieser/Outside Images

Chic St. Barts

Last but definitely not least in this trio of Caribbean treasures is glittering, iconic, breathtaking St. Barthélemy, better known to one and all as St. Barts. Strategically situated smack-dab in the middle of the Lesser Antilles chain, it’s been grappled over by would-be European colonialists and pirates of all stripes for hundreds of years. That said, a quick stroll through the streets of Gustavia, the ­stupendous deepwater port that also ­services the main anchorage, makes one thing very clear: The French were the last ones standing.

St. Barts is synonymous with the best of everything: the tastiest restaurants, ­grandest villas, sleekest yachts and, of course, the most beautiful people. It’s a scene everyone should experience once. And the best thing about arriving on a charter boat is that, once you’ve had your fill, you can simply sail away.

What to know if you go:

Climate: Tropical. There will be plenty of sunshine and high temperatures, as well as occasional squalls that can bring heavy showers. Be prepared for both.

Winds: Trade-wind sailing means easterly breeze generally ranging from 10 to 25 knots. In winter the winds are usually northeast and heavier; in summertime, expect calmer conditions trending southeast.

Sailing level: Line-of-sight navigation is simple and straightforward for experienced sailors of all levels, but above-average boathandling skills may be necessary for open-ocean passages between the islands on the more blustery days.

Herb McCormick is CW’s executive editor.