The short answer
St. Barths and Anguilla sit about 25 miles apart, and both are a short hop from St. Maarten. They attract many of the same travelers. They don't offer the same holiday.
St. Barths is French, hilly and social. You go for Gustavia's harbor, long lunches that turn into evenings, shopping, and a scene that peaks over Christmas and New Year's. Anguilla is British, flat and quiet. You go for long, empty beaches, some of the best food in the Caribbean, and nights that end early by choice.
If you want to see and be seen, choose St. Barths. If you want to disappear for a week, choose Anguilla. The rest of this guide covers the details that should settle it.
Getting there
Anguilla is now the easier island to reach. American Airlines started the first nonstop flights from the U.S. to Anguilla in 2021, from Miami. New nonstops from Boston, Newark and Baltimore followed in December 2025. If you'd rather connect through St. Maarten, the ferry or a private boat to Anguilla takes about 25 minutes. A runway extension now underway should bring larger aircraft in a few years.
St. Barths still takes two legs. No commercial jets land there, so everyone connects. Most guests fly into St. Maarten and take a 10- to 15-minute flight on Winair or St. Barth Commuter. Tradewind Aviation flies in from San Juan and Antigua. The ferry from St. Maarten to Gustavia takes 45 minutes to an hour, and the water can be rough.
Two things to plan around on St. Barths. The airport closes at sunset, so a late arrival into St. Maarten can mean a night there or a boat across. The short runway and small planes also mean tight luggage limits. Ship extra bags ahead, or book a private flight.
For guests flying private, Anguilla's airport can take many private jets directly. For St. Barths, larger jets land in St. Maarten or San Juan, with a short charter flight for the last leg.
How each island feels
St. Barths: a small piece of France
St. Barths is a French overseas collectivity, so it runs on euros, French bakeries and French hours. The island is small and steep, with red-roofed villas stacked on green hills above the bays. Gustavia, the capital, is a harbor town of boutiques and restaurants where yachts tie up stern-to along the quay.
It's social. People dress for lunch, go out most nights, and run into friends from home. In late December, the harbor fills with superyachts and the island is at its busiest and most expensive. For many guests, that is exactly why they go.
Anguilla: wide beaches and room to breathe
Anguilla is a British Overseas Territory. English is spoken, and U.S. dollars are accepted almost everywhere. The island is long, low and flat, with no big town and no high-rises. Most of what there is to do happens on a beach or at a dinner table.
It's quiet in a way St. Barths isn't. The island is mostly locally owned and run, and it has a warm, unhurried rhythm. High-profile guests like it because nobody makes a fuss.
Beaches
Anguilla wins on beaches, and it isn't close. The island has more than 30 of them, and many run for a mile or more of soft white sand. Shoal Bay East is the famous one, with calm, clear water over a reef. Meads Bay has a string of restaurants and a few hotels. Rendezvous Bay looks across the water to St. Martin. On a weekday, you can walk for twenty minutes and see a handful of people.
St. Barths has fewer, smaller beaches, each with its own character. Saline and Gouverneur are wide and undeveloped, with no buildings on the sand. Shell Beach is a short walk from Gustavia. St-Jean is the busy one, with beach clubs and planes landing overhead. Colombier can only be reached by boat or a hiking trail, which keeps it quiet.
If your perfect day is a towel, a book and nobody nearby, Anguilla is the answer. If you'd rather move between a wild beach in the morning and a beach club at lunch, St. Barths makes that easy.
Food and nightlife
St. Barths is French dining with a Caribbean view. Expect long beach-club lunches with rosé, serious French and Mediterranean restaurants in Gustavia, and bakeries for breakfast. After dinner, there are lounges and late bars, and in high season a few spots go until the early hours. Reservations at the best-known places are hard to get over the holidays, so book them when you book the villa.
Anguilla has a reputation for food well beyond its size. Chef-run restaurants line the beaches, and the island is known for grilled local lobster and crayfish. Some of the best meals are at casual places with tables in the sand. Nightlife is mostly beach bars with live music, busiest on weekends, and many nights end with dessert rather than a club.
On both islands, a private chef at the villa is worth having for at least a few nights. It's the best way to eat well without needing a reservation or a car.
Villas: what you get on each island
St. Barths villas are about the view. Most sit on the hillsides, looking down over a bay or out to the neighboring islands. Beachfront homes exist, but there are few of them and they book first. Most villas have two to six bedrooms, and very large estates are rare. Over Christmas and New Year's, many homes require a minimum stay of a week or more, and the best ones are often booked a year ahead.
Anguilla villas are about the beach. Because the island is flat, many large villas sit right on the sand, with a lawn and a pool between the house and the water. Anguilla also has more big estates for groups of 12 to 20, often built as several pavilions around one pool, so families and friends can share a house and still have their own space.
Getting around. You'll want a car on either island, or a driver. St. Barths roads are narrow and steep, and some villa driveways are a test, so a small car or a driver is the better choice. Anguilla's roads are flat and easy, and you drive on the left.
Staff. On both islands, we can arrange daily housekeeping, private chefs and butlers. Ask what's included in the rate and what is billed separately, because it varies from home to home.
Which island fits your trip
New Year's Eve with friends: St. Barths. The harbor, the yachts and the parties are the reason to go that week. Book early and expect holiday minimums.
A big family gathering: Anguilla. Large beachfront estates, calm water for children and grandparents, and an easy direct flight from Miami make it simpler for a group of 15.
A honeymoon or anniversary: either. Choose St. Barths for a hillside villa with a view and dinners out. Choose Anguilla for a quiet house on the sand and nobody else around.
Total privacy: Anguilla. It's easier to go unnoticed on Anguilla, and the beachfront estates make it simple to stay put. St. Barths can be private too, but its social scene means more chances of being seen.
Shopping, style and a busy social calendar: St. Barths. Gustavia's boutiques and the beach clubs are a big part of the trip.
Food first: Anguilla. You can eat very well on either island, but Anguilla's range of chef-run beach restaurants is hard to match.
Can't decide? Do both. The islands are close enough to split a trip, with a private boat or short flight between them. A week in an Anguilla beach house followed by a few nights in St. Barths is a combination our guests ask for often.
St. Barths vs. Anguilla FAQ
Is St. Barths or Anguilla more expensive? Both are among the priciest islands in the Caribbean. St. Barths usually costs more for dining and shopping, and holiday villa rates there are among the highest anywhere. Anguilla can offer more space for the money, especially for large beachfront homes.
Which island is easier to get to? Anguilla. It has nonstop flights from Miami, and nonstops from Boston, Newark and Baltimore began in December 2025. St. Barths always needs a connection, usually a short flight from St. Maarten.
Which island has better beaches? Anguilla has more beaches, and they are longer and emptier. St. Barths has fewer, smaller beaches, some wild and some lined with beach clubs.
Is Anguilla better for families? Generally, yes. Its calm water, flat roads, big beachfront villas and direct flights make it easier with children or a multigenerational group.
Can I visit both on one trip? Yes. The islands are about 25 miles apart. A private boat or a short flight via St. Maarten connects them.
When is the best time to visit? December through April is peak season on both, with Christmas and New Year's the busiest weeks. Late spring is quieter, with better villa availability.
Choose your island with Aspect
Tell us your dates, who's coming and what kind of trip you have in mind. We'll suggest the island that fits, send a short list of villas on it, and handle the flights, transfers, chef and anything else the week needs. If you'd like both islands, we'll plan the move between them too.
Start your Caribbean villa inquiry: www.travelwithaspect.com
