Island Hop Like a Pro: Sint Maarten, Anguilla & St. Barths in One Trip
Series: Island Hop Like a Pro β Vol. 1
The taxi driver at Princess Juliana Airport said it without looking up from the steering wheel.
"Where are you staying?"
Sint Maarten, you told him. Two nights, then Anguilla, then St. Barths.
He nodded slowly, the way someone nods when they recognize a plan they've seen work before.
"Smart," he said. "Most people just stay here. They don't know what's twenty minutes away."
He was talking about one of the best-kept secrets in Caribbean travel β a small triangle in the northeastern Caribbean that holds three completely different travel experiences, connects by ferry in under an hour, and can be covered in a single five-day trip without ever boarding a plane again.
Sint Maarten is your base. Anguilla is twenty minutes away. St. Barths is forty-five. Three islands. Three currencies. Three personalities. One trip.
This is Caribbean island hopping done right.
Your Hub: Sint Maarten / Saint Martin β 2-3 Nights
Sint Maarten is the world's smallest territory shared by two nations β the Dutch side (Sint Maarten) and the French side (Saint Martin) β and it works perfectly as a base because of one simple fact: it has an international airport with direct connections from the US and Europe, and two ferry terminals that launch you toward Anguilla and St. Barths.
Dutch side β Philipsburg: duty-free shopping, casino energy, the famous Maho Beach where planes land so close overhead that the jet blast has been known to knock people off their feet. It's theatrical and slightly absurd and completely worth seeing once.
French side β Grand Case: one of the best stretches of Creole food in the entire Caribbean. The lolos β open-air BBQ shacks lining the beach road β serve fresh grilled lobster at prices that will genuinely surprise you. Grand Case is why food travelers come to Sint Maarten specifically, not just as a transit hub.
What to know: The island uses two currencies β euro on the French side, US dollar on the Dutch side. In practice, USD is accepted everywhere. The language shifts from Dutch/English to French as you cross the invisible border on the main road. No passport check. No gate. Just a sign.
Day Trip #1: Anguilla β 20 Minutes by Ferry
The ferry from Marigot (French Saint Martin) to Blowing Point (Anguilla) takes about 20 minutes. It runs multiple times daily. The moment you step off, you've crossed an international border into a British Overseas Territory β bring your passport, it's mandatory, and carry some USD cash for the departure tax at the port.
Why go: Anguilla has some of the most pristine beaches in the Caribbean. Shoal Bay East β a long arc of white powder sand and calm, transparent water with almost no development in sight β is consistently ranked among the top ten beaches in the world. There are no cruise ships in Anguilla. No mass tourism. No high-rise hotels. The island has made a deliberate choice to stay quiet, and the result is the rarest thing in the Caribbean: a world-class beach where you can actually hear the water.
Best for: Travelers who want empty beaches, elevated dining, and no crowds. Anguilla leans upscale β boutique villas and small hotels dominate β but day visitors can access every beach freely.
Don't miss: Lunch at Hibernia in Island Harbour β one of the most interesting restaurants in the Caribbean, serving food that reflects the owners' travels across Asia and Europe filtered through local ingredients.
Day Trip #2: St. Barths β 45 Minutes by Ferry
The ferry from Oyster Pond or Marigot to Gustavia (St. Barths) is operated by Voyager and The Edge, with multiple daily departures. Crossing time is roughly 45 minutes to an hour depending on sea conditions. St. Barths is a French collectivity β Schengen rules apply, the currency is euro, and the airport is so small that large commercial jets cannot land, which is precisely why the island has stayed the way it is.
Why go: St. Barths is the most glamorous island in the Caribbean. Gustavia's harbor fills with superyachts every December. The boutiques carry the same labels as Paris and Milan. The restaurants serve food that would earn stars anywhere in Europe.
But here's what most people don't know: the beaches are public and free. Colombier Beach on the northwest tip β reachable only by boat or a 20-minute hike down a rocky trail β is one of the most dramatic and beautiful beaches in the region, and it costs nothing to spend the day there. A sandwich from a boulangerie on the hill costs the same as anywhere in France.
St. Barths is not only for the ultra-wealthy. It just requires knowing where to go.
Best for: Travelers who want beauty, design, and a European atmosphere in the Caribbean β without necessarily spending European luxury prices.
The Practical Itinerary
| Day | Where | Highlights |
|---|---|---|
| Day 1 | Arrive Sint Maarten | Settle in, explore Philipsburg |
| Day 2 | Sint Maarten | Grand Case lolos, Maho Beach planes |
| Day 3 | Day trip to Anguilla | Shoal Bay East, lunch at Hibernia |
| Day 4 | Day trip to St. Barths | Gustavia harbor, Colombier Beach hike |
| Day 5 | Depart Sint Maarten | β |
What You Need to Know Before You Go
Passport: Required for all three islands β Sint Maarten to Anguilla and St. Barths are international crossings. Do not leave it at the hotel.
Currency: USD works on Sint Maarten and Anguilla. EUR on St. Barths (USD accepted but at a slight disadvantage). Carry some cash for departure taxes at the ports.
Ferry operators: Sint Maarten β Anguilla (public ferry, daily departures from Marigot). Sint Maarten β St. Barths via Voyager and The Edge (book in advance during high season).
Best season: Mid-November through April. Hurricane season runs June through November β seas can be rough and some ferry services reduce frequency.
One thing most guides don't tell you: Sea conditions between Sint Maarten and St. Barths can be choppy. If you're prone to seasickness, take preventive medication before boarding. The crossing is short but the swells can be significant depending on the season.
Why This Triangle Works
Each island does something completely different.
Sint Maarten gives you energy, logistics, and two cultural identities in the same afternoon. Anguilla gives you silence, nature, and the rarest beaches in the region. St. Barths gives you beauty, design, and a European sophistication that exists nowhere else in the Caribbean.
Three days. Three moods. One base.
That is the essence of Caribbean island hopping β not collecting destinations, but understanding how the right combination creates something greater than the sum of its parts.
Ask Sun AI to help you plan this exact itinerary β π΄
Next in the series: The French Antilles Chain β Guadeloupe, Dominica, Martinique & Saint Lucia by ferry with L'Express des Γles.
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