An Active Explorer's 4-Day Road Trip & Island Guide to St. Martin

Rent a small 4x4 vehicle like a Suzuki Jimny. It is perfect for tight parking, steep hills, and rough roads on the island.

Check into your base. Parking is free, secure, and included, making it an excellent starting point for daily road trips.

Explore the capital of the Dutch side. Walk Front Street for shopping, and check the cruise port schedule beforehand to visit on a low-ship day to avoid crowds.

Parking in Philipsburg can be challenging. Park at Bobby's Marina near the cruise port for a reasonable rate of around $2 per hour.

Stop here for great food, incredible ocean views, and live music performances right on the boardwalk.

Visit the oldest building on the island, a historic white structure featured prominently on the Dutch Sint Maarten flag.

Take the chairlift up Sentry Hill for panoramic views of Philipsburg and Great Bay. Try the mountain tube slide (schooner ride) and look out for wild monkeys. Check the cruise port schedule to visit on a day with fewer ships.

Located near Rainforest Adventures. For $15 cash per person, you get a cup of seeds on a stick, and colorful birds will fly right up to feed on your hand and head.

Drive to the very end of Guana Bay Road, past an old abandoned building, and park on the side of the road to find the marked trailhead for the natural pool hike.

Hike about 1 to 1.5 hours each way along the scenic coastal trail from Guana Bay. Wear sturdy shoes, bring plenty of water, and watch out for sea urchins if you decide to swim.

Enjoy breakfast here while watching mega yachts float by. Check the Simpson Bay Bridge opening times (typically 8:30 AM and 9:30 AM) to catch them passing through. The venue is highly dog-friendly.

Embark on a shared or private boat charter. Opt for the Anguilla day trip for beach hopping, or choose the St. Martin coastal trip to swim with sea turtles.

The first stop on the Anguilla charter. Walk around this tiny, pristine sand spit surrounded by turquoise waters—a true tropical paradise.

A fantastic snorkeling and cliff jumping spot accessible during the boat charter. Jump off the rocky cliffs into the calm, clear waters.

Walk along this world-famous beach. The sand is incredibly soft, the water is perfect, and the vibe is exceptionally laid-back.

Another spectacular Anguilla beach stop known for its pristine shoreline and luxury beachfront setting.

Drive here to access the trailhead to Happy Bay. The road down to Friar's Bay is rough and unpaved, making a 4x4 vehicle like a Suzuki Jimny highly recommended.

Take the easy 10-15 minute walk north from Friar's Bay along a scenic trail to reach this secluded, gorgeous beach. Note that it is a clothing-optional beach.

Located in Marigot, the French capital. Climb up to the historic fort ruins for incredible panoramic views of Marigot harbor, Simpson Bay Lagoon, Anguilla, and Saba. There is a small parking lot that can be tricky to navigate.

Head to Grand Case for lunch or dinner at the local open-air BBQ joints (Lolos) near the pier. There are six to choose from with similar delicious menus. The barbecue ribs and chicken are highly recommended. Take a quick look under the pier for a great photo opportunity.