Four Seasons Resort and Residences Anguilla

Accommodations are the property's most consistent strength. Even entry-level rooms are genuinely spacious, with marble bathrooms that rival many suites elsewhere, walk-in closets, and private terraces with plunge pools or hot tubs. The residences and villas are in another league entirely—full kitchens, washer/dryers, multiple bedrooms with en-suite baths, and in some cases direct beach access. The Kelly Wearstler design reads as slightly dated nearly a decade on, and some soft goods show their age on close inspection, but the bones remain handsome. A persistent, minor complaint concerns shutters rather than blackout curtains, which means early risers are made, not born, here.

The setting is exceptional. Straddling two beaches—Meads Bay's long crescent of powdery sand and Barnes Bay's quieter, rockier cove—the resort offers more shoreline variety than any competitor on the island. Meads Bay connects via a beachside walk to Blanchard's, Straw Hat, and other notable restaurants, which is a genuine luxury. The trade-off is Anguilla itself: reaching the island requires a flight to St. Maarten followed by a ferry or puddle-jumper transfer, and the airport experience can be uneven. Winter months occasionally bring rough surf that makes Meads Bay unsuitable for swimming—a detail the resort could communicate more candidly in advance.

This is where the property has made its most dramatic leap forward. Under the Viceroy, service was the consistent weakness; today, it is arguably the greatest strength. The Anguillan staff bring a warmth that feels culturally distinct from the polished anonymity of other top-tier resorts—staff remember names by day two, greet returning guests as family, and genuinely seem to enjoy their work. Standouts cluster around the Sunset Pool (Del Henry runs that deck like a maestro), the concierge team, and the guest experience managers who handle special occasions with real thoughtfulness. The caveat is scale: when the property is at full occupancy or hosting corporate groups, service can become uneven, with longer waits at the restaurants and occasional lapses in follow-through on concierge requests. It is warmer than Four Seasons Maui, less precise than Four Seasons Hualalai, and decisively better than any other property on Anguilla.

The architecture is the property's signature—dramatic, contemporary, and polarizing. The Sunset Lounge and adult pool, cantilevered over the bluff with unbroken sightlines to the horizon, is one of the most cinematic spaces in the Caribbean. The lobby and common areas read as sophisticated if occasionally austere, and some travelers find the aesthetic cold compared to the softer warmth of Cap Juluca. The grounds are immaculately maintained, the landscaping genuinely lush, and there's no evidence today of the devastation Irma inflicted in 2017. It is, in the end, a resort that photographs spectacularly—and largely lives up to the photographs.

This is the honest weak point. Room rates comfortably exceed $1,500 per night in season, and the nickel-and-diming—mandatory service charges, environmental levies, expensive ferry transfers, punishing taxi fares off-property—adds up quickly. Fitness classes carry additional charges. The food is priced as if it were exceptional, which it isn't quite. Guests who book through Amex Fine Hotels & Resorts or Virtuoso can extract meaningful value through upgrades and breakfast credits, and the villas, priced per bedroom across a large group, actually represent reasonable value. For couples paying retail, it is expensive even by the standards of top-tier Caribbean resorts.

The dining program is competent rather than transcendent, and pricing is aggressive even by Caribbean luxury standards. Salt, the signature restaurant, delivers polished ocean-view fine dining and a breakfast buffet that is genuinely excellent—arguably the best morning spread on the island. Sunset Lounge is the property's social heart, where sushi and craft cocktails are consumed against one of the Caribbean's great sunset views; the live music most evenings gives it real atmosphere. Half Shell, tucked away on Barnes Bay, is the sleeper hit—relaxed, beach-side, and consistently well-executed. The Monday night Barefoot BBQ is a highlight worth planning around. The weakness is value: an 18% service charge layered atop already steep pricing, plus an additional expected gratuity and an environmental levy, means a casual lunch for two easily crosses $150. The wine list, in particular, is thin for the prices charged. For dinner variety, guests are better served walking the beach to Blanchard's, Straw Hat, or Jacala.