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Sint Maarten🇸🇽 | 3 days itinerary

Your 3-Day Sint Maarten Itinerary

By Johan Kruseman 🇳🇱 | Updated October 23, 2026
This three-day plan is for travelers who mainly want sea, food and easy days on the west side of Sint Maarten, with one good hike and a dinner trip to the French side. The pace is relaxed, with mornings for activity and afternoons for swimming. Public minibuses along the Airport Road and Welfare Road cover nearly everything, the lagoon water taxi links the waterfront, and a bus via Marigot or a taxi takes you to Grand Case.

Day 1: Simpson Bay and Maho Beach

Stay all three nights in Simpson Bay, a strip of guesthouses, condos, bars and supermarkets sitting between the airport and the lagoon; it’s 5 minutes from the airport and close to every stop on this route. Once you’re settled, head to Maho Beach for the reason everyone goes: planes coming in so low over the sand that you feel the roar in your chest. The midday wave of wide-body arrivals is the main event, and the beach bars post the day’s schedule. Stand well clear of the fence on departures, because the jet blast can flatten people. … read more 👉
This three-day plan is for travelers who mainly want sea, food and easy days on the west side of Sint Maarten, with one good hike and a dinner trip to the French side. The pace is relaxed, with mornings for activity and afternoons for swimming. Public minibuses along the Airport Road and Welfare Road cover nearly everything, the lagoon water taxi links the waterfront, and a bus via Marigot or a taxi takes you to Grand Case.

Day 1: Simpson Bay and Maho Beach

Stay all three nights in Simpson Bay, a strip of guesthouses, condos, bars and supermarkets sitting between the airport and the lagoon; it’s 5 minutes from the airport and close to every stop on this route. Once you’re settled, head to Maho Beach for the reason everyone goes: planes coming in so low over the sand that you feel the roar in your chest. The midday wave of wide-body arrivals is the main event, and the beach bars post the day’s schedule. Stand well clear of the fence on departures, because the jet blast can flatten people.

Day 2: Cole Bay to Indigo Bay and Simpson Bay Lagoon

Start early on the Cole Bay to Indigo Bay hike, which climbs the dry hills above Cole Bay and drops down to a quiet cove on the south coast. The views over the lagoon and out to Saba on clear days are why you climb; bring 2 liters of water, since there’s little shade after 9 am. In the afternoon, get onto Simpson Bay Lagoon itself, one of the largest inland lagoons in the Caribbean. Rent a kayak or paddleboard, or ride the water taxi between bars, and time a drink near the Simpson Bay bridge for the evening opening, when superyachts squeeze through the channel.

Day 3: Cupecoy Beach and Grand Case

Spend the morning at Cupecoy Beach at the far western end of the Dutch side, where honey-colored sandstone cliffs and small sea caves give it more character than any other beach on this side of the island. Go at low tide, because the sand mostly disappears at high water. In the late afternoon, take a minibus via Marigot or a taxi to Grand Case on the French side for your final dinner. The cheapest and liveliest option is the waterfront row of “lolos”, open-air grills serving ribs, chicken, conch and johnnycakes, and the town’s white-tablecloth restaurants sit just down the same street if you want to splurge.

For a quieter swim, take a taxi from Grand Case to Friar’s Bay and follow the short coastal path over the headland to Happy Bay, a sandy cove with no road access.
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🛏️ Where to stay?The Route Breakdown

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Simpson Bay(Days 1 - 3)

⚠️ This itinerary is intended as inspiration, not a fixed travel plan. Suggested routes and travel times may not always be feasible due to transport availability, seasonal conditions or other local factors. Always verify all travel logistics before booking.

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🧭 RouteGot More or Less Time?

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🙋 FAQCommon Questions

Yes, Sint Maarten is one of the easiest places in the Caribbean to travel on your own: English is spoken everywhere, prices are quoted in US dollars and the Dutch side covers only about 34 square kilometers.

The challenge is cost, not logistics. There are very few hostels, so expect US$60 to 150 a night for a guesthouse or small apartment in Philipsburg or Simpson Bay, and a realistic budget of US$90 to 150 a day. Minibuses cost around US$2 to 4 a ride, and no stop on the Dutch side is more than 30 to 40 minutes from another. Crossing to the French side at Grand Case involves no border checks.
Three to five days is the right amount of time for Sint Maarten; two days covers Philipsburg and the east coast, and five lets you see both sides of the Dutch territory without rushing.

With 2 days, stay in Philipsburg for Frontstreet, the Guana Bay Trail and lunch at Oyster Pond. With 3 days, base yourself in Simpson Bay for Maho Beach, the lagoon and Cupecoy Beach. With 5 days, split 2 nights in Philipsburg and 3 in Simpson Bay and add a hike, a snorkel trip to Pelican Key and dinner in Grand Case. Philipsburg to Simpson Bay takes 20 to 40 minutes, depending on traffic.
Yes, you can get around Sint Maarten without a car, because privately run minibuses connect Philipsburg, Cole Bay, Simpson Bay, Maho and the French side from early morning until early evening.

Fares run about US$2 to 4 a ride, and you flag the vans down anywhere along the main roads. Service is frequent on the Philipsburg to Simpson Bay and Maho corridor, and you can reach Grand Case by changing in Marigot. It thins out after dark and toward Oyster Pond and Guana Bay, where a taxi (fixed fares, roughly US$15 to 30 for short hops) fills the gap. Expect traffic jams around Cole Bay at rush hour.
The must-visits in Sint Maarten are Philipsburg’s Frontstreet and Old Street, Maho Beach with its low-flying planes, Simpson Bay Lagoon and the wild east coast around Guana Bay and Oyster Pond.

Walk Frontstreet after 4 pm, when the cruise crowds leave. Catch the midday wide-body arrivals at Maho Beach, 5 minutes from Simpson Bay. Rent a kayak on the Simpson Bay Lagoon for around US$20 to 30 an hour. Hike the Guana Bay Trail before 8 am to beat the heat, then take a 10 to 15 minute taxi to Oyster Pond for lunch. All of these fit into 3 to 4 days, and most are reachable by US$2 to 4 minibus rides.
If you are short on time in Sint Maarten, skip Dawn Beach, the Yoda Guy Movie Exhibit and the Pelican Key boat trip, and keep your hours for Maho, the lagoon and the Guana Bay coast.

Dawn Beach is pleasant but quiet, and the cliff views on the Guana Bay Trail give you more of the east coast in the same time. The Yoda Guy Movie Exhibit is a 45-minute stop best kept for film fans or a rainy hour in Philipsburg. A Pelican Key snorkel trip takes half a day and costs more than a beach day at Cupecoy. Skip Frontstreet on a four-ship cruise day until after 4 pm, when the crowds thin out.
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