Ride the Sky Explorer chairlift to Sentry Hill, explore a historic plantation, then launch on the Flying Dutchman — the world’s steepest zipline. This half-day tour pairs island history with a high-speed descent and panoramic Caribbean views.
More ways to explore the area's outdoor wonders
The ride begins before your feet leave the ground: the Sky Explorer chairlift eases out over forest and faded sugarcane terraces, carrying riders toward Sentry Hill’s exposed crown. At 1,125 feet the island tightens into a map below — bays, runways, and rooftops shifting beneath a Caribbean wind that seems to dare you to fly.
Difficulty
moderate
Duration
3 hours
Fitness Level
Light to moderate fitness; able to climb short stairs, sit in a harnessed chair and follow safety instructions.
Wildlife
History
Rockland Estate was once part of the island’s plantation network; exhibits at the estate highlight St. Maarten’s Dutch and Afro-Caribbean heritage that shaped its nickname, “The Friendly Island.”
Conservation
Operators emphasize minimal-impact access to the estate and summit; stay on marked paths, avoid littering, and use reef-safe sunscreen to protect surrounding marine habitats.
Reserve your spot on the St Maarten Sky Explorer and The Flying Dutchman Adventure today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Close-toed shoes only
The zipline uses a chair-style harness and requires secure footwear for safe launches and landings; sandals are not permitted.
Know the size limits
Participants must be 52 inches tall and weigh between 100–275 lbs; bring ID to confirm you meet requirements.
Time your visit for calmer winds
Morning departures usually have lighter winds and clearer views, improving both comfort and camera shots.
Hydrate and protect from sun
Bring water and reef-safe sunscreen — the exposed summit is hot and reflective even when breezy.
Closed-toe trail or hiking shoes
Stable footwear is required for harnessing, walking the platforms, and safe landings.
Light windbreaker
Top-of-hill winds and sea breezes can be chilly; a thin layer blocks wind on the descent.
winter
Reef-safe sunscreen & sunglasses
Strong Caribbean sun at altitude increases UV exposure; protect eyes and skin.
summer
Light rain jacket or poncho
Hurricane season and tropical showers can produce brief downpours that may pause operations.
fall