This five-day plan is for travelers who want to see both coasts of Sint Maarten properly: the capital and the wild Atlantic side first, then the lagoon, the beaches and the restaurants of the west, with a dinner hop onto the French side. The pace is relaxed, with one hike or big outing per day and long afternoons left for swimming. Everything runs on the public minibuses that fan out from Philipsburg, plus a short taxi ride where the vans thin out (Oyster Pond, Parotte Ville) and a boat for the snorkel trip to Pelican Key.
Days 1-2: Philipsburg and the East Coast
Start in
Philipsburg, because it puts you within 15 minutes of the island’s best coastal walking and its only real town center. Spend the first afternoon on
Frontstreet and Old Street once the cruise passengers have gone back aboard (usually after 4 pm), when the duty-free shops quiet down, the Boardwalk cafés along Great Bay fill with locals and you can actually look at the old courthouse and the gingerbread trim on Old Street. …
read more 👉This five-day plan is for travelers who want to see both coasts of Sint Maarten properly: the capital and the wild Atlantic side first, then the lagoon, the beaches and the restaurants of the west, with a dinner hop onto the French side. The pace is relaxed, with one hike or big outing per day and long afternoons left for swimming. Everything runs on the public minibuses that fan out from Philipsburg, plus a short taxi ride where the vans thin out (Oyster Pond, Parotte Ville) and a boat for the snorkel trip to Pelican Key.
Days 1-2: Philipsburg and the East Coast
Start in Philipsburg, because it puts you within 15 minutes of the island’s best coastal walking and its only real town center. Spend the first afternoon on Frontstreet and Old Street once the cruise passengers have gone back aboard (usually after 4 pm), when the duty-free shops quiet down, the Boardwalk cafés along Great Bay fill with locals and you can actually look at the old courthouse and the gingerbread trim on Old Street. The Yoda Guy Movie Exhibit sits right on the strip and deserves 45 minutes: it’s a small, personal museum built around the career of a film effects artist, with original props and casts, and it’s far more fun than its name suggests.
On day 2, set out early on the Pointe Blanche to Guana Bay hike, which runs over the rocky headland east of the harbor and onto the windward coast, where the Atlantic slams into cliffs and the wind keeps you cooler than anywhere in town. Carry 2 liters of water and start by 7:30 am; there’s almost no shade. Afterward, take a short taxi to Oyster Pond, a sheltered, horseshoe-shaped bay ringed by yachts, and eat lunch by the marina. From there it’s a few minutes’ walk to Dawn Beach, a long, quiet strip with a reef close to shore and a clear view across to St. Barths on good days.
Day 3: Sentry Hill and Parotte Ville Bird Park
Make the move west a slow one. Check out of Philipsburg, leave your bag with your next guesthouse or a luggage service, and climb Sentry Hill in St. Peters in the cooler morning hours; the summit looks down over Great Bay on one side and the Simpson Bay Lagoon on the other, which gives you the whole shape of the island in one view before you explore the second half of it. Then stop at Parotte Ville Bird Park, a small aviary where macaws and other parrots are the stars and the staff let you get close; plan around 1 to 1.5 hours. A taxi or minibus brings you on to Simpson Bay by mid-afternoon.
Days 3-5: Simpson Bay, Maho and the West End
Simpson Bay becomes your base for the last three nights because it sits between the lagoon, the airport beaches and the western cliffs, so no outing takes more than 15 minutes. Spend your first evening on Simpson Bay Lagoon: rent a kayak or stand-up paddleboard and paddle past the anchored yachts, or hop on the water taxi between the waterfront bars, then catch the drawbridge opening that lets the big boats through into the lagoon.
Day 4 belongs to the west end. Get to Maho Beach before the midday arrivals from North America and Europe, find a spot well back from the fence (the jet blast on departing planes is strong enough to knock people over and throw sand in your face), and check the posted arrival boards at the beach bars. When you’ve had your fill of landing gear overhead, walk or take a van to Cupecoy Beach, where sandstone cliffs and small caves frame a narrow strip of sand; come in the late afternoon for softer light and fewer people, and note that the beach shrinks a lot at high tide.
On day 5, join a morning snorkel boat to Pelican Key, a rocky islet off the south coast where the water around the rocks is clear and you can often spot turtles and rays. Back on land, spend a lazy afternoon on the beach at Simpson Bay, the long, calm crescent behind the airport runway that’s rarely crowded. For your final night, ride a minibus via Marigot or take a taxi to Grand Case on the French side, where the waterfront “lolos” grill ribs, chicken and lobster over open fires and the main street turns into one long dinner table at sunset.
If you have spare energy on the last morning, take a taxi to Loterie Farm on the French side and hike up through the forest to Pic Paradis, the highest point on the island.v2.webp){kind=logo}
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