A Complete 2-Day Plan for Sint Maarten

This two-day plan is for weekend visitors, long layovers and cruise travelers adding a couple of nights, who want the capital, one proper hike and a slow lunch by the water without losing hours in traffic. The pace is brisk on the first afternoon and easy after that. You can do it all on the public minibuses out of Philipsburg, plus one short taxi ride to Oyster Pond, since vans to the east side run less often.

Day 1: Philipsburg

Sleep both nights in Philipsburg, since everything on this route sits within 20 minutes of Great Bay. Drop your bag and head straight to Frontstreet and Old Street, the two narrow parallel lanes behind the beach. Frontstreet is wall-to-wall jewelry, electronics and liquor stores aimed at cruise passengers, so walk it for the white courthouse and the free tastings at the Guavaberry Emporium, the shop that sells the island’s spiced guavaberry liqueur. Old Street is shorter and quieter, with restored wooden buildings and shady courtyards. On a day with four ships in … read more 👉

This two-day plan is for weekend visitors, long layovers and cruise travelers adding a couple of nights, who want the capital, one proper hike and a slow lunch by the water without losing hours in traffic. The pace is brisk on the first afternoon and easy after that. You can do it all on the public minibuses out of Philipsburg, plus one short taxi ride to Oyster Pond, since vans to the east side run less often.

Day 1: Philipsburg

Sleep both nights in Philipsburg, since everything on this route sits within 20 minutes of Great Bay. Drop your bag and head straight to Frontstreet and Old Street, the two narrow parallel lanes behind the beach. Frontstreet is wall-to-wall jewelry, electronics and liquor stores aimed at cruise passengers, so walk it for the white courthouse and the free tastings at the Guavaberry Emporium, the shop that sells the island’s spiced guavaberry liqueur. Old Street is shorter and quieter, with restored wooden buildings and shady courtyards. On a day with four ships in port, the strip is packed until about 4 pm, so save your wander for late afternoon and finish with a cold drink on the Boardwalk as the sun drops behind the hills.

Day 2: Guana Bay Trail and Oyster Pond

Get up early for the Guana Bay Trail, which follows the exposed windward coast past cliffs, surf and cactus scrub. It’s a completely different island from the calm Caribbean side: wind, salt spray and almost no one else around. Start by 7:30 am, bring 2 liters of water and wear real shoes, because the ground is loose rock. From there, a 10 to 15 minute taxi gets you to Oyster Pond, a sheltered, almost circular bay full of sailboats, where the line between the Dutch and French sides runs across the water. Have a long lunch at the marina, swim if the restaurant has a dock, and ride back to Philipsburg in the late afternoon.

On a spare hour, walk out to Fort Amsterdam on the Little Bay peninsula, where old Dutch walls and cannons look straight back across Great Bay to Philipsburg.