The Island, Your Way

Private Island Day in St. Maarten

Both countries in a day is genuinely doable. Both countries plus a proper lunch is better.

The shape of a good day

The island is 37 square miles and you can drive around it in two hours. That means an island day is not about covering ground — it is about choosing four or five places and giving them enough time.

Here are three shapes that work. All of them are suggestions, not itineraries.

The two-country day

Marigot for the market and the harbour, up to Grand Case for lunch on the strip, over to Orient Bay for the afternoon, back through the Dutch side at dusk. Roughly six hours, most of it out of the car.

This is the one to pick if it is your only full day.

The quiet day

Cupecoy and Mullet Bay in the morning while they are still empty, a long lunch somewhere with no view of a cruise ship, and Baie Rouge or Friar's Bay in the afternoon.

Better on a heavy port day, when Philipsburg and Maho are at their worst.

The high road

Up through the middle of the island for the views over Simpson Bay lagoon, along the ridge, down to the French side. Shorter, about four hours, and the best option if someone in the group does not want a whole day of it.

What we will tell you honestly

Orient Bay is worth it, but it is 45 minutes each way from the Dutch side, so it wants to be the destination rather than a stop on the way to somewhere else.

Maho is about the aircraft. If the landing schedule is thin that afternoon, we will suggest somewhere else and you will have a better day for it.

Philipsburg on a four-ship day is not a pleasant place to walk around. We will route around it rather than through it.

The Simpson Bay bridge will cost you twenty minutes if you hit it wrong, and we plan the day around the published openings rather than discovering them.

From a ship

The same day works on a port call, cut to fit your all-aboard. We plan backwards from the time you have to be on the gangway and build the day inside it, with margin.

Back on board in time is guaranteed. See from the ship.

What it costs

Priced by the block — four, six or eight hours — per vehicle rather than per person, with fuel, parking and waiting included. A group of six pays the same as a couple.

Entrance fees, loungers and lunch are yours. We will tell you what things cost before you commit to them.

Questions people actually ask

How long does it take to drive around St. Maarten?

Without stopping, about two hours for the full loop. That is not a day out, it is a lap. A real island day is five to six hours because the stops are the point.

Do I need a passport to cross to the French side?

No. There is no border post, no checkpoint and no stamp — just a sign at the roadside. Bring photo identification as a matter of sense, but nobody will ask for it.

Can we decide as we go?

Yes, and most people do. We will suggest a shape for the day based on the weather and what is on, then change it when you see somewhere you would rather stay longer.

Is a private tour better than a bus tour?

For the same money as two coach seats you often get the whole car. The real difference is that you stop when you want to and leave when you want to, rather than at the pace of the slowest person on a forty-seat bus.

Everything under this

  • A Beach Club Day A driver for a beach club day on St. Maarten. Dropped at the lounger, collected when you are ready, with an honest view of which club suits which group.
  • A Shopping Day Front Street and Marigot in a day, with somewhere to put the bags. Duty-free on the Dutch side, French goods and the market on the other.

Also worth reading

Checked and updated 4 September 2026.