Trade snow boots for sandals and airport chaos for Caribbean calm—because winter is better spent in St. Maarten, the friendly island where wellness, flavor and fun collide.
From the moment we landed at Princess Juliana International Airport, greeted by warm smiles (and warmer air), the stress of deadlines and frozen mornings melted away. St. Maarten may only be 37 square miles, but this little island packs enough adventure, indulgence and culture to fill an entire season of travel daydreams.
Day One: Welcome to Paradise
Our home base for the week was Oyster Bay Beach Resort, a laid-back luxury retreat perched between the Caribbean Sea and the Atlantic Ocean. After check-in, we kicked things off the right way—with welcome cocktails at sunset, followed by dinner at Big Fish, an elegant coastal restaurant that fuses South Beach glamour with island soul. The fresh snapper and coconut mojitos alone were worth the flight.
Day Two: Barbecue, Boats and Beach Thrills
Morning began with breakfast overlooking the ocean. By lunchtime, we were at Captain’s Rib Shack, one of St. Maarten’s famous “Lolos”—open-air roadside eateries serving up smoky, soulful barbecue. Locals say it’s the best on the island, and after one bite of their ribs, we believed them.
Next up was pure adrenaline: a Rhino Safari Tour, where we steered our own mini boats along the island’s coast to secluded Happy Bay Beach. The turquoise water begged for snorkeling, and between the coral, sea turtles and laughter, we lost all sense of time. We capped the day with dinner and drinks at Tortuga (if you watch Below Deck, you’ll recognize it!), a beachfront spot at Maho Beach where planes roar overhead as you sip your rum punch—an only-in-St.-Maarten thrill that never gets old.
Day Three: St. Barths—Luxe Living, Island Style
Thanks to St. Maarten’s perfect location (nicknamed the Crossroads of the Caribbean), hopping to nearby St. Barths was a breeze. After a scenic ferry ride, we explored Gustavia’s chic boutiques and harbor cafés before heading to La Guérite Beach—a slice of heaven serving Mediterranean-Caribbean fusion under the palms. Chef Yiannis Kioroglou’s curated menu was fresh, vibrant and impossibly photogenic.
After a sun-soaked afternoon, we ferried back to St. Maarten for dinner at Infinity Restaurant, where candlelight, sea breezes and local seafood made for a dreamlike end to the day.
Day Four: Culture, Carnival and Cocktails
No trip is complete without a dose of local flavor—and Philipsburg, the colorful capital, delivered in full technicolor. We strolled the lively boardwalk, admired sprawling murals from the island’s post-pandemic art renaissance and stopped by We Culture SXM, an immersive museum celebrating Carnival’s costumes, music and heartbeat.
Later, we traded history for happy hour at Balaou Floating Bar—yes, it’s literally a bar on the water—where island rhythms, cocktails and sunset views reminded us that wellness isn’t always yoga mats and meditation. Sometimes, it’s dancing barefoot on a floating deck with new friends. Dinner at Le Piment, a French bistro in Orient Bay Village, brought the night full circle with laughter, wine and perfectly seared seafood.
Day Five: Until Next Time
Our final morning was slow and sweet—a quiet breakfast on the terrace, one last swim in Oyster Bay’s infinity pool and a reluctant glance at flight itineraries.
As our plane took off over the sparkling coastline, one thing was clear: St. Maarten is more than a tropical escape—it’s a state of mind. A place where art, food, adventure and hospitality blend effortlessly, and where you leave feeling lighter than when you arrived.
This winter, skip the snow. Let St. Maarten warm your body, your soul and your sense of wonder.
If you go:
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Stay: Oyster Bay Beach Resort, St. Maarten
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Don’t miss: Rhino Tours, Maho Beach, We Culture SXM, Balaou Floating Bar, and a day trip to St. Barths
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Best for: Travelers craving sun, sophistication, and a little island adventure
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Visit: vacationstmaarten.com
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