The Ultimate St. Maarten Itinerary
Plane spotting, beach club bliss, and the Caribbean’s best sunset sail
If you’re dreaming of Caribbean blues, beachfront brunches, and a quick hop to Anguilla, this 5-day/4-night St. Maarten itinerary hits the sweet spot. From plane-watching thrills at Maho Beach to a luxurious sunset sail, here’s how to soak up every drop of island magic.
Where We Stayed: Fourteen at Mullet BayModern and ocean-facing, this upscale condo-hotel is a perfect home base—just a short walk to Mullet Bay and minutes from everywhere you want to be.
Day 1: Arrival & Maho Beach Plane Spotting
Afternoon: After landing at Princess Juliana Airport, you’re practically already there—Fourteen at Mullet Bay is less than 10 minutes away. Check in, unpack, and take a short stroll to stretch your legs.
Late Afternoon: Head over to Maho Beach, the world-famous spot where planes soar just overhead as they land. It’s thrilling, surreal, and totally Instagram-worthy.
Evening: Grab dinner at Sunset Bar & Grill or Moulin Fou in Maho Village—both perfect for a relaxed first night with ocean views and tropical cocktails.
Day 2: Mullet Bay Picnic + Massage by the Ocean
Morning: Ease into island time with a picnic on Mullet Bay Beach—fresh fruit, pastries, and coffee. Swim, read, and soak up the soft white sand and calm surf.
Afternoon: Make your way to Sonesta Ocean Point Resort for a massage by the ocean. Their open-air spa bungalows offer an unforgettable setting—waves crashing below while you drift into full vacation mode.
Evening: Grab a casual dinner at 3 Amigos or order in and enjoy dinner on your balcony.
Day 3: Day Trip to Anguilla (Details in Next Post)
Full-Day Excursion: It’s time to explore Anguilla, just a quick ferry or charter boat away. You’ll visit picture-perfect beaches like Shoal Bay or Meads Bay, enjoy lunch at a beachfront café, and return in time to watch the sun dip below the horizon. (Full details here.)
Day 4: Kalatua Beach Club + Sunset Sail
Morning–Afternoon: Reserve a beach bed at Kalatua, the chic beach club right on Mullet Bay. Sip cocktails, order fresh seafood, and enjoy a stylish, laid-back day with beachside service.
Tip: Reserve both lunch (the restaurant has a extensive menu versus the beach menu) and beach beds in advance (tend to book fast especially after 12pm).
Late Afternoon: Head to Simpson Bay for a sunset catamaran sail. It’s the perfect final-night sendoff—complete with open bar, tropical snacks, and golden Caribbean skies.
Tip: Book the evening sail in advance to lock in a great sunset slot. Check out our top rated recommendations for sunset and day sails via viator.
Day 5: Rainbow Café Brunch & Farewell
Morning: Drive to Rainbow Café in Grand Case for one last luxury meal with your feet in the sand. The food is stellar and the beach vibes are unbeatable.
Tip: Book this advance through their website.
Midday: Head back to your hotel, pack up, and check out. If time allows, grab one last gelato or do a final beach walk at Cupecoy.
Where to Stay: Fourteen at Mullet Bay
- Vibe: Sleek condo-style hotel with ocean views, kitchenettes, and a prime location
- Perks: Walkable to Mullet Bay Beach, minutes from Maho and Simpson Bay
- Why It Works: Feels like your own private paradise—but with hotel comforts
Final Travel Tips
- Rent a car: Makes exploring both the French and Dutch sides a breeze
- Bring water shoes: Great for rocky beach entries and exploring tide pools
- Currency: USD and Euros are both accepted, depending on the side of the island
Recap at a Glance
| Day | Highlights |
| Day 1 | Arrival + Maho Beach plane spotting + dinner |
| Day 2 | Mullet Bay picnic + massage at Sonesta |
| Day 3 | Day trip to Anguilla (separate post coming) |
| Day 4 | Kalatua beach club + sunset catamaran sail |
| Day 5 | Rainbow Café brunch + checkout |
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