Jet Trails and Quiet Moments in St. Maarten

Sailing into St. Maarten cruise port is always a thrill, whether it’s your first visit or your fifteenth. The bright buildings of Philipsburg (Philipsburg – Pronounced [FILL-ips-burg]) stretch along the waterfront like a row of painted postcards, backed by green hills and crowned by sunshine.

St. Maarten is a dual-nation island, half Dutch and half French, with a culture shaped by centuries of trade and resilience. It’s one of the few places in the world where you can walk across an international border in minutes and be met with warm smiles on both sides.

This island has long been a personal favorite. It’s familiar and nostalgic, but never quite the same twice.

Between 2004 and 2008, I returned to St. Maarten every spring for two glorious weeks at a timeshare. I spent my days beach-hopping from Cupecoy to Club Orient, grabbing pastries in Marigot and enjoying dinners with my feet in the sand. That era of travel was carefree and sun-drenched, and the island became one of my most treasured getaways.

But in 2017, Hurricane Irma tore through the Caribbean, and St. Maarten suffered heavily. My 2018 return was sobering. On a rainy spring day, I boarded a bus tour around the island, quietly passing crumbling buildings I once knew well. It wasn’t the lively escape I remembered, but the island’s spirit still showed in every patch of fresh paint and smile from a local shopkeeper.

When I came back again in 2023, the mood had shifted. I wandered through Philipsburg before heading out to Maho Beach to watch planes land at SXM airport. Sitting at Sunset Bar with a cold drink, I watched jets roar just feet overhead as they touched down behind the beach. It was the perfect mix of thrill and reflection—a moment that reminded me why I keep coming back.