St Barts and Anguilla are two of the Caribbean’s most established luxury villa destinations, both reachable through St Maarten, both known for privacy and high-end villas rather than resort strips. The islands themselves, though, are genuinely different — in terrain, in character, and in how you get there.
Getting There
Neither island has direct flights from the US mainland. St Barts’ Gustaf III Airport has a short runway that limits landings to small aircraft — the connection from St Maarten (SXM) is a roughly ten-minute flight on a Twin Otter-sized plane, or a 45-minute-to-one-hour ferry to Gustavia. Anguilla’s Clayton J. Lloyd International Airport takes slightly larger aircraft and is reachable via one-stop routes through St Maarten or San Juan, with some seasonal direct flights from the US in winter; the ferry from St Maarten’s Marigot to Anguilla’s Blowing Point terminal is shorter, at about 20 minutes.
Terrain and Setting
St Barts is hilly and volcanic, around eight square miles, with villas built into slopes and headlands across the island’s many small bays and hillside areas. Anguilla is flat coral and limestone, longer and narrower at roughly 16 miles by 3 to 3.5 miles, with a highest point of only 240 feet. That difference shapes the villas: St Barts has more hillside, view-driven properties; Anguilla’s villas sit closer to sea level, closer to its beaches.
Beaches
Anguilla is known specifically for its beaches — it has roughly 33 named beaches, generally calm and white-sand, with Meads Bay, Shoal Bay, Rendezvous Bay, and Maunday’s Bay among the most cited. St Barts has fewer, smaller beaches spread across its many named areas, with genuine beachfront villa access concentrated in three areas: Flamands, Lorient Beach, and St Jean.
Character
St Barts is a French collectivity, with Gustavia’s harbour town, French and international dining, and boutique shopping as a real part of the stay. Anguilla is a British Overseas Territory, English-speaking, generally quieter and less built up around dining and nightlife, with the beaches themselves as the main draw.
Which Fits Your Trip
If walkable restaurants, a harbour-town evening, and hillside villas with long views matter to the trip, St Barts is the more direct match. If the beach itself — its length, its calm water, having more of it — is the priority above everything else, Anguilla’s beach-first geography is built for that. Neither is a lesser version of the other; they’re different islands with different strengths.
Exploring St Barts Villas
See our guide to every St Barts area to compare the island’s beachfront, hillside, and harbour-town options, or browse the full villa collection. For help planning a St Barts stay, reach out directly.