Philipsburg Cruise Port

Here’s the bucket list for your day ashore: the most extraordinary thing to do at each stop, who runs it, and how to book it direct — so you can weigh it against your ship’s excursion and pick what suits you.

1snorkel

Random Wind 'Paradise Day Sail' — Schooner Sail, Snorkel & the Original Tarzan Swing

Sail out of Bobby's Marina aboard a 54-foot wooden schooner-rigged catamaran to a secluded snorkel cove, then launch yourself off the boat on the famous original Tarzan rope swing into impossibly blue water. Lunch is cooked fresh on board, the bar is fully open, and all snorkel gear, life jackets and noodles are included for the 10am–3pm run. This is a genuine sailing experience under canvas — not a motor-cat with a sail bolted on — which is why it's the marquee water excursion in St. Maarten.

We have not yet verified a bookable operator and price for this one, so we are not quoting either.

What to expect, timing & how to book →

2landmark

Maho Beach — Jets Landing Over Your Head (the island's signature postcard)

Stand on a strip of sand at the end of Princess Juliana airport's runway as widebody jets thunder in just meters over your head on final approach, then brace as departing jet blast literally blows beachgoers across the sand into the surf. Check the 'WiFi' surfboard flight board at the Sunset Bar to time the big arrivals — peak action is roughly 11:30am to 4pm, 50+ planes a day. A first-timer who skips this has missed the one thing St. Maarten is famous for worldwide.

We have not yet verified a bookable operator and price for this one, so we are not quoting either.

What to expect, timing & how to book →

3eco-park

Flying Dutchman — World's Steepest Zipline + Sky Explorer Chairlift

Ride the Sky Explorer chairlift up to Sentry Hill, the island's highest peak, for a panoramic crawl over the rainforest canopy down to the sea, then strap in and drop off the world's steepest zipline. It's the port's marquee adrenaline experience, set in the Rockland Estate rainforest with full Caribbean views the whole way down. Book a time slot ahead so it locks neatly inside your port window.

Book it St. Maarten: Sky Explorer and Flying Dutchman Entry Ticket $109 per person

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What to expect, timing & how to book →

4scenic

12 Metre Challenge — Crew a Real America's Cup Racing Yacht

Become working crew on an authentic former America's Cup 12-metre racing yacht and go head-to-head against a second guest-crewed boat in a real two-hour race off Philipsburg. Grind the winches, trim the sails, take a turn at the helm, or just hold on and watch the rail dip into the Caribbean — no sailing experience needed, ages 6+. It's been voted a top Caribbean shore excursion for years and it's a genuinely talk-worthy one-off you can't get most places.

We have not yet verified a bookable operator and price for this one, so we are not quoting either.

What to expect, timing & how to book →

5city

Bernard's Tours — Two Countries, One Island (French & Dutch sightseeing)

St. Maarten is the smallest landmass on earth split between two nations, and Bernard's open-air bus is the island's most-loved local outfit for actually seeing it: Maho plane-spotting, the French capital Marigot, Grand Case viewpoints and the two-flags border monument, all in one loop with genuinely entertaining guides. It's the best way for a first-timer to grasp the whole island instead of just shopping the pier. Pickup is under the white tent at Port Services, a ~4-minute walk from the ships, and it's timed around cruise schedules.

Book it The Best of St Maarten Private Sightseeing Tour $450 per person

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What to expect, timing & how to book →

6snorkel

Sail The Phoenix 'Luxury Day Sail' — the upscale catamaran alternate

The roomier, more polished sail option: a 62-foot Privilege luxury catamaran out of Bobby's Marina for a 10am–3pm cruise to a guided snorkel stop, with paddleboards and an 18-foot floating mat to play on. Complimentary drinks, fresh fruit, cake and a freshly cooked lunch are served onboard, and the boat runs at 72% capacity so it never feels packed. This is your low-risk near-port safety net if Random Wind is full — same Philipsburg marina, same cruise-friendly timing, more space and a luxury frame.

We have not yet verified a bookable operator and price for this one, so we are not quoting either.

What to expect, timing & how to book →