Philipsburg, Sint Maarten

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This Leeward island has been famously bisected into French and Dutch territories since 1648, and is referred to both as Saint Martin and Sint Maarten. In their respective capitals—Marigot and Philipsburg—there are ancient stone forts and candy-colored buildings lining winding streets. The Dutch side has a slightly larger population but is a bit smaller, at 34 square kilometers (13 square miles), versus the 53-square-kilometer (20-square-mile) Saint Martin.

Named for its founder John Philips, Philipsburg, the capital of the Dutch side, has some excellent international art galleries, thumping discos and popular casinos. Farther afield are beautiful beaches and a seemingly endless array of nature conservancies. With them come extensive opportunities for adventure—hiking, biking and zip lining—and amazing wildlife sightings in the sea, on land and in the sky.

On the French side, there are cafés serving café au lait and pain au chocolat and sidewalk bistros offering chilled rosé and savory crepes. A variety of luxury shops and cosmopolitan boutiques beckon to sophisticated shoppers who love a good bargain—the entire island has no sales tax.