Philipsburg and the Dutch Side

Philipsburg is a short drive from the Simpson Bay resort area — ten, fifteen minutes on a good day, all on the Dutch side, roads that are easy to navigate even if you have only been on the island for 24 hours. Drove myself, which is the right way to do it: stop where you want, stay as long as you want, leave before the cruise ship crowds peak. Philipsburg gets busy. Having your own car means you do not have to participate in that.

Philipsburg was founded in 1733 as “Nieuwe Durp” — literally “New Village” — which is the kind of name you give a place when you are a Dutch colonist and have not slept in three months. Five years later they renamed it after John Philips, a Scotsman who served as the Dutch commander of the island, because apparently the Dutch were comfortable outsourcing both their military leadership and their town-naming rights. The capital of the Dutch half of Saint Martin is a narrow strip of land wedged between Great Bay and the Great Salt Pond, and walking through it feels like visiting somewhere that has been rebuilt more times than it wants to talk about. Which it has.

The Boardwalk and the Courthouse

The Great Bay Boardwalk runs about a mile and a half along the waterfront, wooden planks over sand, with the kind of ocean view that makes you forget you are walking past souvenir shops selling shot glasses and magnets. Historical markers along the way — cannons from the colonial era mounted on pedestals with plaques that explain which European power was shooting at which other European power at the time. The Caribbean has a lot of cannons. Every island has them. They are the most honest tourist attraction in the region because they do not pretend the history was pleasant.

The Courthouse is the anchor of Front Street, the main drag. Built in 1793, white wood with green shutters and a clock tower topped by a carved pineapple finial — the universal symbol of hospitality, which is a strange thing to put on a building that has also served as a jail, a fire station, and a post office over the centuries. It has been rebuilt after hurricanes multiple times, each version slightly different from the last, but the pineapple survives. It always survives.

Street Art and Leaving Hearts Behind

If you want context for what you are looking at, a guided walking tour of Philipsburg is worth doing at least once. The history here goes well beyond colonial cannons — the island changed hands seventeen times between European powers, and a good guide can make that legible in a way that the plaques do not quite manage.

I found the mural by accident, which is how you are supposed to find murals. Part of the ColorMeSXM project, organized by the Be the Change Foundation — 21 murals scattered around Philipsburg by the artist Efenio. This one says “I left my heart in St. Maarten” in the kind of bright, layered lettering that was designed specifically for people to stand in front of with their phones out. I am people. I stood in front of it with my phone out. If you want to find all 21 rather than stumble across them at random, there are guided mural walking tours of Philipsburg that trace the full ColorMeSXM route.

The self-guided version is still a legitimate way to spend an afternoon if you like walking and do not mind sweating through your shirt. The art ranges from island pride to political commentary to pure color for the sake of color. Most of the murals went up after Hurricane Irma as part of the rebuilding effort, which gives them a weight that goes beyond aesthetics. They are not decoration. They are defiance.

Willy the 7th

On Cole Bay Hill there is a bronze statue of a man sitting on a bench, gazing out over the island. This is William Henry Bell II, known as “Willy the 7th,” who died in 1950 at just 33 years old. His family owned the Cape Bay Estate, and his descendants later allowed the government to erect the national flag pole on the hilltop where his statue now sits. It is one of those monuments that tells you more about the island than any museum could — a young man from a prominent local family, commemorated not for conquest or politics but for his connection to the land itself. The Sint Maarten flag flies behind him, and from where he sits you can see most of the Dutch side laid out below.

Indian Food, Because the Caribbean Is More Than You Think

Here is something that surprised me more than it should have: there is a real Indian and Sindhi merchant community on Sint Maarten, with roots going back decades. The result is genuinely good Indian food on a 34-square-mile Caribbean island, and it does not feel like an anomaly. It feels like part of the fabric. I had a green herb-crusted dish with a side salad that would have been right at home in any Indian restaurant in a major city, and the fact that I was eating it a ten-minute drive from a beach with iguanas on it only made it better.

Two Countries, No Border

I crossed between the Dutch and French sides several times during the trip and never once showed a passport. No checkpoint, no gate, no booth. According to local legend, the border was originally set by a footrace: a Frenchman started from one side and a Dutchman from the other, and where they met became the line. The Frenchman covered more ground because the Dutchman stopped to drink jenever along the way. Whether or not this is true — it is almost certainly not — it is the kind of origin story that tells you exactly how the island feels about its own division. A formality. A quirk of history that the locals shrug at and the tourists find fascinating.

What Irma Left Behind

I should mention Hurricane Irma, because you cannot talk about Saint Martin honestly without it. September 2017. Category 5. Sustained winds of 185 miles per hour for more than 30 hours. Ninety-five percent of buildings on the island damaged. Sixty percent rendered uninhabitable. Three billion dollars in destruction. By late 2021, four years later, the rebuilding was far from complete. You could see it everywhere — roofless concrete shells next to freshly painted shops, construction equipment parked in vacant lots that used to be hotels, tarps where walls should have been. The island was functional. Tourists were coming. But the scars were visible on every block, and pretending otherwise would be dishonest.

Philipsburg is not a place that asks for sympathy. It is a place that keeps going. The murals go up over the damage. The boardwalk gets rebuilt. The pineapple stays on the courthouse. And the roosters — they made it through Irma too, obviously. Nothing stops the roosters.

Practical Notes for Getting It Right

The boardwalk is at its best in the late afternoon, after the cruise ships have pulled out and the waterfront exhales. By midday — when two or three ships are docked simultaneously and the duty-free shops are running at full capacity — Front Street feels like a Carnival with a better rum selection. If you arrive then, it is still worth doing. Just know what you are walking into.

If duty-free shopping is part of the plan, a guided Philipsburg duty-free shopping experience through Viator is worth considering if you want someone else to navigate the forty nearly-identical rum shops and jewelry stores for you.

And if Philipsburg is one stop among several, a full Sint Maarten island drive gives you the boardwalk and the French side and the salt pond overlook all in one loop — a better use of the day than trying to stitch it together yourself on unfamiliar roads.