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Philipsburg is one of the most cosmopolitan cities in the Caribbean, with a beachfront that can feel more like South Beach than a secluded Caribbean escape. This unique island outpost boast a friendly blend of Dutch and West Indian cultures, and though the capital itself is quite small—about a mile wide by three or four block deep—it offers something for everyone.
Day 1: Dig into St Maarten’s history
Start with a visit to the St. Maarten Museum, where you can see artifacts from Fort Amsterdam and the shipwreck of the British frigate HMS Proselyte, which sank nearby. Then head to the other side of town to explore the ruins of the town’s original colonial defenses. Right on the edge of town, Fort Willem sits atop Fort Hill, offering great views of the bay and the chance to wander among the foundations of the fort. Continue farther west, passing through the Divi Little Bay Beach Resort, to find Fort Amsterdam at the end of the peninsula.
Day 2: Shop till you drop
As you walk down Front Street, it won’t be hard to understand why Philipsburg is one of the top shopping destinations in all the Caribbean. The entire island is duty-free, which means you can find great, tax-free deals on high-dollar items like electronics, jewels, perfume and much more. Front Street is the unequivocal heart of the island’s high-end shopping, so if you’re game, you can spend a full day or more perusing.
Day 3: Kick back on the beach
Great Bay Beach runs the entire length of the town, so no matter where you are in Philipsburg, you’re never more than a few blocks from the beach. And this wide strip of soft sand is the ideal spot to spend a day touching up your suntan. The recently added beachfront boardwalk is a 50-foot-wide pedestrian thoroughfare where you can walk or bike among local crafts vendors. Along the way you can find beach chairs for rent—some proprietors will even throw in a bucket of cold beers with the chair rental—and whenever hunger hits, you can pull up a chair at a nearby restaurant without leaving the beach.