Two flags, one island—and unlimited ways to play. St. Martin (French Saint-Martin) and St. Maarten (Dutch Sint Maarten) share 37 square miles of beachcombing, snorkeling, Creole kitchens, and lively music. The “Friendly Island” nickname is well-earned: locals love to chat, and the border is invisible, so you can start your morning with a butter-scented croissant in Marigot and end with steel drums at Simpson Bay.

History here reads like a sea tale—Arawak and Carib roots, colonial forts, salt ponds, and a modern revival after Hurricane Irma, with markets and marinas humming once again. Food is a highlight: barbecue smoke curls from Grand Case “lolos,” while French bistros and rum distilleries tempt you across the map. Beaches range from social (Orient Bay, Maho) to secluded (Happy Bay, Tintamarre).

Practical notes: The Dutch side commonly uses USD and 110V US-style outlets; the French side uses EUR and 220V European outlets (many stays provide adapters). Driving is on the right; renting a car makes exploring easy, though taxis are plentiful with set rates. Hurricane season runs June–November; book flexible plans and watch the forecast.

Philipsburg (Dutch Side)

Philipsburg hugs Great Bay with a palm-lined boardwalk, colorful facades, and duty-free boutiques—an easy base for beaches, boat trips, and nightlife in nearby Simpson Bay and Maho. From here, hit Mullet Bay’s aquamarine water, zip down “The Flying Dutchman,” and time your sunset with jumbo jets gliding over Maho Beach.

• Top sights nearby: Great Bay Boardwalk, Fort Amsterdam (pelican nesting site), Maho Beach plane spotting, Mullet Bay, Rainforest Adventures St. Maarten (ziplines), Guavaberry Emporium tastings.
• Where to stay: Stay beachfront on Great Bay or at Little Bay for calm water; Simpson Bay is ideal for nightlife and dining. Browse stays on VRBO and compare hotels on Hotels.com.
• Getting there: Fly into SXM (Princess Juliana). Check fares on Trip.com or Kiwi.com (from Europe also see Omio for flight options). Taxis are fixed-rate (SXM to Philipsburg ~20–25 USD); rental cars run ~50–80 USD/day.
• Great eats: Breakfast at Coffee Lounge (Philipsburg) or Zee Best (Simpson Bay); lunch at The Greenhouse or Lazy Lizard on the Boardwalk; dinner at Skipjack’s (lobster), Sale & Pepe (Italian by the lagoon), or Emilio’s (elevated Caribbean at Rockland Estate). For casual late-night, try Soggy Dollar Bar or Dinghy Dock.
• Featured activities: Sightseeing loop, ATV adventure, rum tour, and a dreamy dinner cruise (see days below for links).

Day 1: Arrival, Boardwalk Stroll, and Sunset Start

Afternoon: Land at SXM and breeze to your stay. Pre-book a smooth ride with this local service if you prefer not to rent a car: Transportation Services in St Maarten.

Check in, then wander the Great Bay Boardwalk for sea views and duty-free browsing. Cool off with gelato at Carousel (Simpson Bay) if you’re nearby.

Evening: Golden hour at Fort Amsterdam—follow the headland from Little Bay for pelican flyovers and harbor views. Dinner on the Boardwalk: The Greenhouse (grilled mahi sandwich, addictive fries) or Lazy Lizard (jerk chicken, johnny cakes). Nightcap at Soggy Dollar Bar with live music.

Day 2: Island Highlights Tour, Marigot Market, and Maho Jets

Morning: Fuel up at Zee Best (almond croissants, omelets) or Coffee Lounge (iced latte, açai bowls). Join an island sampler that hits both sides without the logistics stress: FUN DAY St.Maarten Island Sightseeing Tour with Beach.

Afternoon: Expect photo stops at Oyster Bay, swim time at Orient Bay, and browsing at Marigot’s waterfront market (look for fresh spices and guavaberry jams). Time your arrival at Maho for big-jet landings—late lunch at Sunset Bar & Grill or pizza and potent rum punch at Driftwood Boat Bar.

Evening: Simpson Bay dinner picks: Skipjack’s for grilled lobster and conch fritters, or Sale & Pepe for handmade pasta with a lagoon breeze. Cocktails at JAX Steakhouse’s bar if you want something sleek.

Day 3: ATV Coastline Thrills and Beach Hopping

Morning: Light breakfast at Top Carrot (smoothies, breakfast burritos), then rev up for a guided ride that straddles both sides of the island: For hotel guests: Guided ATV Tour Dutch/French St. Maarten - Highlights & Beach.

Expect scenic overlooks, 15–20 minute photo stops, and a cool-down dip.

Afternoon: Relax at Mullet Bay—calm water, powder sand, and a couple of casual shacks for burgers or johnny cakes. Bring a snorkel to the rocky ends for schools of sergeant majors.

Evening: Dinner at Emilio’s in a restored plantation building (call for reservations—try the tamarind glazed ribs or local fish). If you’ve got energy, check out Lotus in Simpson Bay for a late DJ-led scene.

Day 4: Philipsburg History, Rum & A Lagoon Dinner Cruise

Morning: Walk Old Street for pastel storefronts and island-made crafts. Pop into the Guavaberry Emporium to sample the island’s namesake liqueur and learn the story behind it.

Afternoon: Toast the island’s sugarcane heritage on a guided rum outing: Taste of Caribbean Culture and Rum Factory Tour.

You’ll blend history with tastings and a scenic coastal stop.

Evening: A romantic finale on the Dutch side: drift through Simpson Bay Lagoon under the stars on this intimate cruise with a multi-course dinner, ideal for couples or small groups: Private Tropical Gondola Dinner Cruise Simpson Bay.

Grand Case + Orient Bay (French Side)

Just 30–40 minutes from Philipsburg, Grand Case is the island’s culinary capital—a beachfront village of fine French dining, Creole “lolo” grills, and wine lists that rival big cities. Nearby Orient Bay delivers active beach days: catamarans, parasailing, and chic clubs with Mediterranean menus.

• Top sights nearby: Grand Case Beach and pier sunsets, Orient Bay water sports, Pinel Island (iguanas and shallow snorkeling), Anse Marcel’s calm cove, Happy Bay via a short coastal hike.
• Where to stay: Beachfront apartments in Grand Case for sunset views, or a suite near Orient Village for walkable cafés. Browse VRBO and compare hotels on Hotels.com.
• Getting there from Philipsburg: No flights or trains—simply taxi (~25–35 USD) or drive ~30–40 minutes across the border. If you prefer a driver with meet-and-greet, you can also book Transportation Services in St Maarten for point-to-point rides.
• Great eats: Breakfast at Sarafina’s (Marigot) or Croissant Royal; lunch at the Grand Case “lolos” (Talk of the Town for ribs and grilled lobster); beach club dining at Kontiki, Bikini, or Coco on Orient; refined dinners at Le Pressoir (rum bar and tasting menu), Ocean 82 (sea views), Bistrot Caraibes (lobster thermidor), or Spiga (Italian-Caribbean).
• Featured activities: Luxury picnic on the sand, multi-beach day with locals’ favorites, and a culinary walking tour (see days below for links).

Day 5: Transfer to Grand Case, Market Browsing, Sunset Dining

Morning: Depart Philipsburg after breakfast; if it’s a market day, stop in Marigot’s waterfront market for spices, island art, and fresh fruit. Grab pastries at Sarafina’s (butter-rich croissants, fruit tarts) before checking into Grand Case.

Afternoon: Beach time on Grand Case—snorkel along the rocks and stroll the pier. For a secluded cove, hike 15 minutes from Friar’s Bay to Happy Bay; bring water and a sun hat.

Evening: Dinner crawl: Start with a ti’ punch or rum flight at Le Pressoir, then Ocean 82 for sea-breeze fine dining (tuna tartare, butter-poached lobster). Alternatively, go casual at the lolos—order ribs, johnny cakes, and plantains at Talk of the Town and watch the grills flare at dusk.

Day 6: Pinel Island and A Luxury Beach Picnic

Morning: Catch the quick ferry from Cul-de-Sac to Pinel Island (boats run frequently during the day). Wade into calm, shallow water and snorkel for turtles around the far side; iguanas patrol the sand near the beach bars.

Afternoon: Return to Orient Bay for water sports—try a short catamaran sail or parasailing. Grab a leisurely late lunch at Coco Beach (whole grilled fish) or Bikini Beach (tuna tartare, salads).

Evening: Celebrate with a private, styled spread right on the sand: Luxury Private Picnic in Paradise Beach.

Think pillows, lanterns, and a golden-hour feast as the sea turns to glass.

Day 7: Three Beaches or Culinary Tour, Then Departure

Morning: If you want one last beach hop, join a locals-led circuit that hits the island’s favorites with time to swim and relax: St Maartens Three Beach Locals Choice.

Prefer to eat your way out? Opt for the island’s beloved food walk with stories and tastings: Small-Group Culinary Culture Tour in St. Maarten.

Afternoon: Quick lunch in Grand Case (Bistrot Caraibes lobster roll or a final plate at the lolos), then transfer to SXM. Weekends can be busy—arrive 2.5 hours before departure. Check flight status and options on Trip.com or Kiwi.com.

Optional/Alternate Picks You Can Swap In

• Want a private island overview instead of a group tour? The Best of St Maarten Private Sightseeing Tour.

  

• Prefer a two-nation highlights loop with flexibility? Two Islands, Twice the Fun.

  

Eat & Drink Cheat Sheet (by vibe):

• Breakfast/coffee: Coffee Lounge (Philipsburg), Zee Best (Simpson Bay), Sarafina’s (Marigot), Croissant Royal (Marigot), Top Carrot (Simpson Bay).
• Beach bites: Driftwood Boat Bar (Maho), Mullet Bay beach shacks, Bikini/Kontiki/Coco (Orient Bay), Rainbow Café (Grand Case beach club).
• Local & Creole: Talk of the Town (Grand Case lolo), Caribbean Blend (Philipsburg for rotis and curries).
• Date night: Ocean 82 (sea views), Le Pressoir (rum-forward tasting menu), Emilio’s (heritage setting), Sale & Pepe (lagoon-side pasta).
• Nightlife: Soggy Dollar Bar (dockside live bands), Lotus (club), Casino Royale (Maho) for a flutter after dinner.

Summary: In one week you’ll trace both sides of St. Martin—splashing at Orient Bay, savoring Grand Case dinners, and catching your breath as jets skim Maho. Between beach picnics and rum tastings, you’ll collect the flavors, sounds, and sea breezes that make “The Friendly Island” a place people return to again and again.