The road climbs quickly from Phillipsburg, past pastel shops and rum shops, into green hills that smell of wet leaves and salt. The rooster runs quickly down the narrow road. A trailhead sign points inside. As you reach the first lookout, the port appears as a bright strip below, with cruise ships docked on one side and the ocean stretching out towards Anguilla on the other. Trade winds pass through the trees. This is St. Maarten, and the feel of the island changes as you move away from the beach.
Most travelers know this 37-square-mile island for its white sand beaches and long lunches. Spending a day inland or on the water under your own power brings your secondary identity into focus. Hills, reefs, open waterways and persistent winds have transformed this dual-state island into one of the most active destinations in the northeastern Caribbean.
Here’s how to do it:
Into the Hills: Rainforest and Ridge Trail
Start early on the Dutch side Rockland EstateThis is where the Rainforest Adventure Park is located. You can take the steep Sky Explorer chairlift to the top of Sentry Hill, the highest point on the island at 1,125 feet, and then follow marked trails through lush vegetation. A tree frog cuts through the silence. The iguana clings to a branch on the road. The summit platform offers a panoramic view of the Caribbean Sea and the Atlantic Ocean.
Where serious hikers head pick paradis On the French side. The trail winds through dry forests and shady valleys to reach the island’s highest point, 1,391 feet. The final section becomes narrower and steeper. There are so many ledges at the top that there is no overlook, just open rock and wide views across Grand Case, Orient Bay and nearby islands in the distance. Please bring water. Wear real shoes. The terrain is uneven, and the thinning canopy allows the sun to shine directly on it.
closer to the coast, beach nature park Near Cay Bay, you can enjoy guided horseback rides along dirt trails and the coastline. You move and scrub between cacti and emerge onto a quiet curve of sand with no hotel in sight. The ride is stable and controlled, perfect for beginners, but the setup feels distant.
The steepest zipline in the world
St. Martin’s claims bragging rights in the air. to Rainforest Adventure at Rockland Estateyou will find flying dutchmanIt is widely considered to be the steepest zipline in the world. The experience begins with: Sualiga Sky Explorer The chairlift that takes you to the top Century HillAt 1,125 feet above sea level, it is the highest point on the Dutch side. The summit platform offers clear 360-degree views across Phillipsburg, Great Bay and nearby islands.
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The Flying Dutchman is approximately 2,800 feet long and drops to approximately 1,050 feet, taking you down a mountainside at high speeds in a seat-mounted harness. The hills quickly disappear and the harbor comes into focus as you descend to the bottom of the estate.
Come back to earth again Emilio Wilson MuseumIt is housed in a restored farm building that details the island’s cultural and historical story. Just a few steps away, Emilio’s Restaurant It serves Caribbean-influenced cuisine in a stone-walled restaurant overlooking the hills.
Crossing over to the French side, the terrain shifts again. near the top pick paradisThe island’s highest peak, 1,391 feet; lottery farm It combines zip lines, hiking trails and an elevated obstacle course within a lush rainforest. that flight areaThe course travels across several lines and suspension bridges built into the hillside canopy. The platform is set in dense greenery and the course varies in length and speed, making it suitable for both beginners and experienced riders.
Wind and Water: Open Water Sailing
St. Maarten’s maritime reputation. The island hosts an annual event. St Martin Heineken RegattaRecruit competitive crews from around the world and enjoy year-round access to the same conditions that challenge the pros.
Take a day sailing in Simpson Bay. Monohulls and catamarans depart daily, most often in small groups of 12 to 20 passengers. Within 30 minutes, the coastline thins and the sea changes from turquoise to dark blue. The crew typically sets a course for Tintamarre or Pinel Island on the French side, dropping anchor on an empty beach where you can snorkel over coral heads and sea fans (Pinel also offers great hiking).
If you want to take control of the helm and have some experience, several operators offer half-day and full-day ferry charters. The waterway between St. Maarten, Anguilla and St. Barths carries steady winds and waves. I can feel the boat heel. The line is tightened. Salt water touches your forearms as you trim the sails.
Sunset sails are more subdued but still athletic. The catamaran motors past Maho Beach as the plane descends low over the sand, then turns west toward the ocean. The coastline glows gold and then fades. The music is kept low. The focus is forward, on the horizon.
Adrenaline on the Atlantic side: kitesurfing and more
Orient Bay on the French side is the island’s wind corridor. In the late morning, colorful kites fill the sky. The beach here is wide and white. The water near the shore is shallow and further out. Several certified schools offer beginner and intermediate kitesurfing lessons with wireless equipped helmets and jet ski support.
Beginners start learning to fly a kite in the sand. Once in the water, the wind does most of the work. The attraction is immediate and physical. Once the board is level and finds its balance, the shoreline begins to slide rapidly. More experienced riders start off with small jumps just offshore, their boards flashing in the sunlight.
Windsurfing and wing foiling have also become popular here, especially during the winter trade wind season. Renting equipment is simple and instructors will tailor sessions to your level.
On mild days, go to: mullet bay or dun beach You can enjoy stand-up paddleboarding and kayaking. Paddle along the edge of the rocks to spot sea urchins and small reef fish below. Water clarity is strongest in the morning before boat traffic increases.
Beneath the Surface: Reefs and Shipwrecks
Divers look for variety in tight spaces. The island’s Dutch and French Marine Park protects several reef systems and shipwreck sites, accessible by short boat rides from Simpson Bay and Oyster Pond.
that convert reefFormed around a 19th-century British warship wreck, it lies in depths of 15 to 40 feet, making it accessible to beginners but still interesting to experienced divers. Coral growth covered most of the wreckage. Schools of blue tang and major sergeants are gathered near the structure.
For more in-depth information, see sites such as: The Bridge and Man of War Shawl Descend along coral ridges occasionally visited by nurse sharks and southern stingrays. Visibility often exceeds 60 feet. Dive operators operate morning trips consisting of two tanks and return before early afternoon.
Snorkelers can access healthy reefs just offshore at: Little Bay Creole Rock near Grand Case. Bring your own mask for flexibility, or join a guided snorkeling sail that combines several stops.
Two countries, one playground
The island’s fractured nature adds scope. You can travel from the Dutch side to the French side in just a few minutes and no passport control is required. Phillipsburg’s boardwalk is flat and busy, making it ideal for long runs at sunrise before cruise passengers disembark. Marigot’s waterfront offers a unique flow, with fishing boats unloading near the market and ferries departing for Anguilla and St Barth.
Cyclists ride the hills between Cole Bay and Oyster Pond. But traffic jams require confidence and visibility equipment. Mountain bike groups sometimes organize guided off-road rides on inside tracks and less developed routes.
If you prefer engines to endurance, ATV tours take place along inland dirt roads and less traveled coastal areas. Your guide will stop at an observation deck and quiet beach for swimming before returning with your small group.
Where to stay between outings
Your location affects your recovery after a day outside.
On the French side, Grand Case Beach Club (one of our favorite hotels in the Caribbean) is steps from calm waters and a short walk from restaurants on Grand Case Boulevard. The rooms open onto a balcony overlooking Anguilla. You can swim in the bay in the morning and hike the 10-minute drive to Pic Paradis in the afternoon. And there’s a new pool deck and bar.
On the Dutch side, Sonesta Ocean Point Resort Maho offers quick access to Simpson Bay marina for sailing departures. Adults-only all-inclusive accommodations include a beachfront suite, three swimming pools, and Azul restaurant, where you can enjoy dinner after a long day on the water.
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You can spend a week in St. Maarten without repeating a single beach. Adding elevation, wind, and open water will expand your island. In one trip, you can hike to the highest point, sail across international waterways, dive at historic shipwrecks, and learn how to fly a kite in the steady trade winds.
Bring sneakers along with sandals. Bring reef-safe sunscreen and a dry bag. The beach is still here. So are the hills, the wind, and the open sea just beyond the harbor.
