Island Hop Like a Pro: Sint Maarten, Anguilla & St. Barths in One Trip
Series: Island Hop Like a Pro — Vol. 1
There is a small triangle in the northeastern Caribbean that quietly holds three of the most distinct travel experiences in the entire region — and you can cover all three in a single trip without ever boarding a plane. Sint Maarten, Anguilla, and St. Barths each have a completely different soul, currency, and cultural identity, yet they sit so close together that ferries connect them in under an hour.
This is Caribbean island hopping done right.
Your Hub: Sint Maarten / Saint Martin
Sint Maarten is the world's smallest territory shared by two nations — the Dutch side (Sint Maarten) and the French side (Saint Martin) — and it works perfectly as your base of operations. The island has an international airport with direct connections from the US and Europe, a wide range of hotels across all budgets, and two ferry terminals that launch you toward Anguilla and St. Barths.
Stay here: 2–3 nights. Explore both sides of the island — Philipsburg on the Dutch side for duty-free shopping and casino energy, Grand Case on the French side for the best Creole food in the Caribbean. Lolos (open-air BBQ shacks) line the beach road in Grand Case and serve fresh grilled lobster at prices that will surprise you.
What to know: The island uses two currencies — the euro on the French side and the US dollar on the Dutch side. In practice, USD is accepted everywhere. The official language switches from Dutch/English to French as you cross the invisible border on the main road.
Day Trip #1: Anguilla — 20 Minutes by Ferry
Anguilla is technically a British Overseas Territory, which means the moment you step off the ferry from Sint Maarten, you have crossed an international border. Bring your passport — it is mandatory for everyone, including US citizens.
The ferry from Blowing Point (Anguilla) to Marigot (French Saint Martin) runs multiple times daily and takes about 20 minutes. The departure tax at the port is paid in cash, so carry a few US dollars.
Why go: Anguilla has some of the most pristine beaches in the Caribbean. Shoal Bay East is consistently ranked among the top ten beaches in the world — a long arc of white powder sand and calm, transparent water with almost no development in sight. The island has no cruise ships, no mass tourism, and no high-rise hotels. It is the quietest luxury destination in the region.
Best for: Travelers who want empty beaches, elevated dining, and no crowds. Anguilla leans upscale — boutique villas and small hotels dominate — but day visitors can access the beaches freely.
Day Trip #2: St. Barths — 45 Minutes by Ferry
St. Barths (Saint-Barthélemy) is a French collectivity, which means it operates under French law, uses the euro, and has an airport so small that large commercial jets cannot land. The ferry from Gustavia (St. Barths) to Oyster Pond or Marigot (Sint Maarten) is operated by Voyager and The Edge, with multiple daily departures.
Crossing time is roughly 45 minutes to one hour depending on sea conditions. Schengen rules apply at the border — most nationalities enter without a visa as they would entering France.
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, and the restaurants serve food that would earn stars anywhere in Europe. But the island is not only for the ultra-wealthy — the beaches are public and free, and a good sandwich from a boulangerie on the hill costs the same as anywhere in France.
Best for: Travelers who want beauty, design, and a European atmosphere in the Caribbean. Colombier Beach on the northwest tip, reachable only by boat or a 20-minute hike, is one of the most dramatic beaches in the region.
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 landing) |
| Day 3 | Day trip to Anguilla | Shoal Bay East, lunch at Hibernia |
| Day 4 | Day trip to St. Barths | Gustavia harbor, Colombier Beach |
| Day 5 | Depart from Sint Maarten | — |
What You Need to Know Before You Go
- Passport: Required for all three islands. Sint Maarten to Anguilla and St. Barths are international crossings.
- Currency: USD works on Sint Maarten and Anguilla. EUR on St. Barths (USD is accepted but at a slight disadvantage).
- Ferry operators: Sint Maarten ↔ Anguilla (public ferry, daily), Sint Maarten ↔ St. Barths via Voyager and The Edge.
- Departure taxes: Paid in cash at the port when leaving Anguilla and Sint Maarten. Carry USD.
- Best season: Mid-November through April. Hurricane season runs June through November — seas can be rough and some ferry services reduce frequency.
Sun's Insider Take
This triangle works so well because each island genuinely offers something different. Sint Maarten gives you energy and logistics. Anguilla gives you silence and nature. St. Barths gives you beauty and culture. Three days, three moods, one base — that is the essence of Caribbean island hopping.
For deeper guides to each destination, explore yourcaribbeanexpert.com.
Next in the series: The French Antilles Chain — Guadeloupe, Dominica, Martinique & Saint Lucia by ferry with L'Express des Îles.