St Barts and Anguilla sit twenty miles apart in the northern Caribbean, both are byword destinations for luxury villas, and they could hardly be less alike. St Barts is French, chic, and social — designer boutiques, celebrated beach clubs, and a harbour full of yachts. Anguilla is British, barefoot, and serene — thirty-three of the finest white-sand beaches on earth and almost nobody on them. This guide compares them properly, so you can choose the right island and book your villa direct, with no platform fees.
At a glance
Choose St Barts for glamour, scene, shopping, and the famous New Year season. Choose Anguilla for the best beaches in the Caribbean, quiet, and a surprising food scene. Both are reached through St Martin, and they are a short hop apart — so you can also do both.
St Barts: French chic
St Barthélemy built its reputation on discretion and style. Development is capped, hotels are small, and villas are the way to stay — hillside estates with ocean-view pools and staff, tucked above the beaches. Gustavia, the harbour capital, is the hub for designer shopping and superyacht-watching; St Jean is the lively beach with the clubs and boutiques; and Gouverneur and Saline in the south are wild, undeveloped, and beautiful. The dining is genuinely French and genuinely excellent. And the island peaks at New Year, when it becomes the most glamorous address in the Caribbean and villas book a year ahead. Our luxury villas in St Barts range from couples’ retreats to large staffed estates.
Anguilla: barefoot luxury
Anguilla is flat, coral, and quiet — and it has the beaches. Shoal Bay East is routinely ranked among the best in the world: two miles of powder-white sand and shallow turquoise water. Meads Bay, Rendezvous Bay, and Maundays Bay are barely less spectacular. There are no cruise ports, no high-rises, and no crowds. What surprises people is the food: for a small, quiet island, Anguilla is arguably the best-eating place in the Caribbean, from barefoot beach shacks at Sandy Ground to serious restaurants. Our luxury villas in Anguilla are beachfront hideaways and large staffed estates, many with the sand at the door.
Head to head
Beaches
Anguilla, decisively. This is not really a contest — Anguilla’s beaches are among the finest in the world, longer, whiter, calmer, and emptier than anything on St Barts. St Barts’ beaches are lovely; Anguilla’s are extraordinary.
Scene and nightlife
St Barts, comfortably. Beach clubs, bars, shopping, and a see-and-be-seen culture that peaks over the festive weeks. Anguilla has live music and beach bars, but it goes quiet early.
Dining
Closer than you would expect. St Barts has more French fine dining and more scene. Anguilla has the better beach-shack-to-fine-dining range and, many would argue, the better food overall. Call it a draw — both are outstanding.
Villas
St Barts for hillside ocean-view estates with staff and privacy, generally more compact given the terrain. Anguilla for beachfront — flat and coral, it has far more villas that genuinely sit on the sand, and more space for the money.
Shopping
St Barts. Gustavia is a duty-free run of French designer boutiques. Anguilla does not really do shopping, and does not pretend to.
Families
Anguilla. The beaches are shallow, calm, and safe, the pace is easy, and the villas have room. St Barts works with children, but Anguilla is built for them without trying.
Privacy
Anguilla for genuine disappearing; St Barts for privacy with a scene close by when you want it.
So which should you choose?
Go to St Barts if you want glamour, shopping, and a social scene, if you are planning a milestone celebration or the New Year, or if the idea of an island with nothing to do at night fills you with dread.
Go to Anguilla if the beach is the point — if your ideal day is a spectacular stretch of empty sand, a long lunch, and a great dinner, with nobody watching. It is the discreet choice, and the one people who could go anywhere often make.
Or do both
Both are reached via St Martin — St Barts by a ten-minute flight or a ferry, Anguilla by a twenty-five-minute boat. That makes a two-island trip genuinely easy: a few days of Anguilla’s beaches, then St Barts for the glamour, or the other way round. Many travellers add a night or two in St Martin for the food at Grand Case. See our full Caribbean collection — our concierge plans the connections.
When to visit
Both run a high season from mid-December to April — dry, sunny, and warm. The festive weeks are the peak on both, and on St Barts they are a phenomenon: New Year in Gustavia is the busiest, most expensive, and most glamorous week in the Caribbean, and villas are taken a year in advance. The shoulder months — late spring and early summer — offer the same beaches with far better value and far fewer people. September and October are the quietest, within hurricane season, when some restaurants close.
Book your villa direct
We book every villa directly — no platform fees, one point of contact, and a concierge to arrange chefs, transfers, flights, boats, and reservations. Tell us your dates and your group, and we will tell you honestly which island suits you — then send a curated shortlist from St Barts, Anguilla, or both.
Cost — and where the money actually goes
Neither island is inexpensive, and in high season both are firmly at the top of the Caribbean market. The difference is what you get for it. On St Barts, the premium buys scene and address: the villas are hillside, generally more compact because the terrain demands it, and a great deal of the budget goes on restaurants, beach clubs, and the sheer cost of being on the island in season. On Anguilla, the same money more often buys house and beach — flat, coral, and low-density, the island has far more villas that sit directly on the sand, with more bedrooms and more space. For a group of eight, Anguilla will usually give you the better house. For a couple who want to be where the action is, St Barts earns its keep. Over the festive weeks, book either a year out; prices and availability both move sharply.
Getting around
Both islands are small and easily driven. On St Barts the roads are steep, narrow, and winding — the classic hire is a small car or a Mini Moke, and nowhere is more than twenty minutes away. Anguilla is flat and straightforward, with easy roads and short distances between the beaches. In both cases our concierge arranges the car or a driver, and on St Barts in particular that is worth taking: parking in Gustavia in high season is its own small ordeal.
Frequently asked questions
Which has better beaches, St Barts or Anguilla?
Anguilla, clearly — its beaches are among the best in the world, longer, whiter, calmer, and far less crowded.
Which is better for families?
Anguilla — shallow, calm water, an easy pace, and beachfront villas with space. St Barts is more social and more hilly.
How do I get to each?
Both via St Martin (SXM). St Barts is a ten-minute flight or a ferry; Anguilla is about twenty-five minutes by boat.
Can I visit both in one trip?
Easily — they are a short hop apart, and many travellers combine them, often with a night or two in St Martin.
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