Four Seasons Resort and Residences Anguilla
A 35-acre clifftop sanctuary where Barnes Bay meets Kelly Wearstler cool.
Why Go
Perched on a coral bluff between Meads Bay and Barnes Bay, this is Anguilla's most cinematic address ΓÇö a resort that trades stuffy formality for barefoot glamour, with pools that seem to spill straight into the Caribbean and villas roomy enough to disappear into for a week.
The Experience
Arrive and the pace immediately shifts. The 35-acre estate is designed like a small hillside village: guest rooms and suites cluster along the ridge with sweeping westward views, while multi-bedroom villas sit directly on the sand of Barnes Bay with private pools and full kitchens. Kelly Wearstler's interiors ΓÇö marble, brass, hand-carved woods, textured neutrals ΓÇö feel more residential than hotel, so evenings tend to unfold slowly: a swim in the adults-only infinity pool at sunset, cocktails at Sunset Lounge as the DJ warms up, then a long, unhurried dinner. The staff-to-guest ratio shows in the small things (someone remembers your coffee order by day two), and the layout means you can genuinely be as social or as invisible as you want.
What to Try
Book a table at Lima Limon for coastal Mexican and mezcal cocktails timed to the sunset over the bay. Do at least one treatment at the ocean-view spa ΓÇö the open-air cabanas let the trade winds and surf soundtrack the massage, and the spa-only infinity pool is a hideaway most guests never find. Order the sushi and a Champagne cart pour at Sunset Lounge before dinner, take a paddleboard out from the Barnes Bay beach at first light, and, if you're staying more than three nights, ask the concierge to arrange a private boat charter to Sandy Island or Prickly Pear Cays for a lunch that ruins other beach days for you.
Insider Tip
The 'standard' ocean-view rooms are among the most generously sized on the island, so don't automatically upsell yourself into a suite ΓÇö instead, put the budget toward a villa on the sand for one or two nights of your stay and a room on the ridge for the rest. You'll get both the private-plunge-pool fantasy and the resort's best sunset views. Also: the adults-only infinity pool tends to empty out around 3ΓÇô4 pm when guests head to nap before dinner ΓÇö that's the golden hour to claim a lounger.
The Practical Stuff
Address: Barnes Bay, 2640, Anguilla (northwest coast, about 20 minutes from Clayton J. Lloyd International Airport or a 25-minute boat transfer from St. Martin's Blowing Point ferry). Five restaurants and bars on property, three pools including an adults-only infinity and a kids' pool, full-service spa, fitness center, and complimentary non-motorized watersports on Barnes Bay. Rates are ultra-luxury ΓÇö expect entry-level rooms from roughly US$1,200ΓÇô2,000/night in shoulder season and villas from US$5,000+ in high season. Book direct through Four Seasons or a Preferred Partners travel advisor for room upgrades, resort credit, and complimentary breakfast.
Pair It With
- Sandy Island — A tiny palm-dotted sandbar a short boat ride away ΓÇö the classic Anguillian lunch-and-swim day trip that pairs perfectly with a return to the resort's spa in the afternoon.
- Blanchards Beach Shack — For a barefoot, no-reservations lobster roll and rum punch lunch on Meads Bay when you want a break from resort dining without leaving the neighborhood.
- Roy's Bayside Grill Guide — A long-running Anguillian institution for casual island fare and local color ΓÇö the perfect counterpoint to a night of tasting menus back at the resort.
- Shoal Bay East — Widely considered one of the Caribbean's finest stretches of sand; a 30-minute drive across the island for a full-day beach change of scenery.