Four Seasons Resort and Residences Anguilla
anguilla, anguilla · ★★★★★
The Verdict
Worth it for your honeymoon?
Four Seasons Resort and Residences Anguilla sits on Barnes Bay and the crescent of Meads Bay's western edge — a 35-acre, contemporary-architecture resort that opened in 2016 after Four Seasons took over the former Viceroy Anguilla property and rebranded it under their flagship management. The architecture, by Kelly Wearstler, is a deliberate counterpoint to Cap Juluca's moorish-traditional vocabulary: clean lines, dark stone, walnut, and limestone, with angular oceanfront villas perched along a cliff above Barnes Bay. The resort spans two beaches — Barnes Bay (Wearstler's signature dramatic cliff-side architecture) and Meads Bay (the more traditional Caribbean white-sand crescent). It is the most architecturally bold resort on Anguilla, with the Four Seasons service standard layered over a property whose design ambition rivals the Aman properties. For honeymooners, the appeal is twofold: the headline Wearstler architecture (the jagged stone walls, the infinity pool cantilevered over the bay, the dark-and-light contrast that photographs spectacularly) and the consistent Four Seasons execution that delivers the most reliable luxury service in the Caribbean. The dining is exceptional — Coba Cellar by Pierre Schaedelin, Bamboo Bar, and the casual Sunset Lounge.
- ✓Prioritise spa & wellness
- ✓Want direct beach access
- ✓Are willing to invest in once-in-a-lifetime
- →Need a strictly adults-only resort
- →Have a budget under $1,000/night
- →Prefer boutique & intimate properties
Score Breakdown
92/100
Book Your Stay
Check availability
We compare Four Seasons across partners and redirect to the cheapest option.
At a Glance
Room Recommendation
Which room to book
The One-Bedroom Oceanfront Villa with Pool is the canonical Four Seasons Anguilla honeymoon accommodation — a standalone Wearstler-designed villa on the cliff above Barnes Bay with a private infinity plunge pool cantilevered over the water, walls of glass that retract entirely, an outdoor terrace dining setup, and dramatic black-and-white interiors. For couples wanting the absolute apex, the Three-Bedroom Beachfront Residence rents on a per-bedroom basis and includes private chef and butler service.
No Surprises
True cost breakdown — 7 nights for two
Based on mid-range rooms, premium-economy flights from Europe, full dining and signature experiences. Adjust for your actual travel profile.
| Item | Estimated Cost |
|---|---|
| Room (7 nights avg $2,350/nt) | $16,450 |
| Flights (2 pax, economy/premium) | $1,800 |
| Airport transfers / seaplane | $200 |
| Dining & drinks (beyond room) | $24,675 |
| Excursions & experiences | $700 |
| Spa / signature treatments | $300 |
| Tips & service (8%) | $3,290 |
| Total estimated | $47,415 |
Day by Day
Your 7-night honeymoon itinerary
Arrival via SXM at Barnes Bay
Fly into Sint Maarten (SXM) and connect via 7-minute Tradewind private charter to Anguilla's Clayton Lloyd International (AXA) — Four Seasons' preferred partner. The 15-minute resort transfer drops you at the dramatic stone porte-cochère with welcome rum punches. First afternoon at the cliffside infinity pool above Barnes Bay, sunset cocktails at Bamboo Bar (the Wearstler-designed lobby lounge), and dinner at Coba Cellar — Pierre Schaedelin's farm-to-table Caribbean-Mediterranean tasting menu.
Meads Bay Beach Day
Walk five minutes from Barnes Bay to Meads Bay — Anguilla's most luxurious-resort-lined beach (Malliouhana, Carimar, and Four Seasons' second beach). Spend the morning at the Meads Bay beach club with the Four Seasons beach service. Lunch at Blanchards Beach Shack — the most famous casual Anguilla restaurant directly on Meads Bay sand. Afternoon spa day at the Four Seasons Spa with a couples' treatment, dinner at Sunset Lounge.
Sandy Island Boat Day
Charter a boat (15 minutes) to Sandy Island — the iconic offshore sandbar restaurant where you eat grilled lobster on a wooden table on a strip of sand surrounded by 360-degree turquoise. Spend three hours on Sandy Island, then return for cocktails at the Four Seasons beach club. Evening at Pimms in Sandy Ground or the Four Seasons casual SALT restaurant.
Shoal Bay East Snorkel
Drive 30 minutes northeast to Shoal Bay East — Anguilla's other postcard beach with the island's best snorkeling reef directly offshore. Beach day at Shoal Bay with lunch at Uncle Ernie's BBQ or Gwen's Reggae Grill (the legendary beach shacks). Return at 4pm for the Four Seasons sunset experience and dinner at Coba Cellar.
Prickly Pear Catamaran
Full-day catamaran charter to Prickly Pear Cays — two uninhabited offshore islands with the clearest snorkeling reef in Anguilla, an hour northeast by boat. Johnno's or Calypso operate full-day trips with grilled lobster lunch on the beach. Return for cocktails at Bamboo Bar and dinner at Hibernia — chef Raoul Rodriguez's Asian-Caribbean fusion in Island Harbour, considered Anguilla's most creative restaurant.
Spa Day & Sunset at Sunshine Shack
Slow morning, then a 90-minute couples' treatment at the Four Seasons Spa — eight treatment rooms in a tropical garden setting with hydrotherapy pool. Late afternoon drive 15 minutes to Bankie Banx's Dune Preserve and Garvey's Sunshine Shack on Rendezvous Bay — the legendary reggae-rum-and-ribs beach shack where everyone on Anguilla goes for sunset. Return to Four Seasons for final dinner at Coba Cellar.
Final Morning & Departure
Final breakfast at SALT overlooking Barnes Bay, a last swim in the cliffside infinity pool. Four Seasons arranges the private charter back to SXM for international connections — most US East Coast flights connect through SXM mid-afternoon, build a 2-3 hour buffer for the connection.
Honest Assessment
What to know before you book
Barnes Bay (the cliffside main beach) is more dramatic than swimmable — Meads Bay (a 5-minute walk) is the calmer swim beach.
Many top Anguilla restaurants close Monday and Tuesday in low season — plan reservations 1-2 weeks ahead.
Hurricane risk runs July through October with peak August-September; verify travel insurance for storm cancellations.
All access via SXM Sint Maarten with a 7-25 minute charter or ferry connection — build buffer for the international onward connection.
Pre-Arrival
Email to send the hotel
Subject: Honeymoon inquiry — Four Seasons Resort Anguilla Dear Reservations team, We are planning our honeymoon [DATE]-[DATE] and are interested in a One-Bedroom Oceanfront Villa with Pool. Please advise on availability, honeymoon amenity, Coba Cellar tasting menu pre-bookings, and Four Seasons Spa couples' treatment availability. Thank you, [Your names]
Send 2 weeks before arrival. Fill in names, dates, and preferences. Hotels respond to personalised requests.
FAQ
Frequently asked questions
Good for honeymooners?
Four Seasons Anguilla is one of the most architecturally distinctive Caribbean honeymoon resorts — the Kelly Wearstler design language, the cliffside Barnes Bay positioning, and the consistent Four Seasons service make it a top-three Anguilla pick alongside Cap Juluca and Aurora. Honeymooners are a dominant demographic, especially in the Oceanfront Villas with private pools.
Best time to visit?
December through April is peak season — dry, sunny, and trade-wind-cooled. May, June, and November are excellent shoulder months with lower rates and warm water. Avoid August through October peak hurricane months. The resort generally stays open year-round but verifies storm risk in September.
Book in advance?
Oceanfront Villas with Pool book 4-6 months ahead for December-March. The few standalone Beachfront Residences book 12 months ahead and only at peak. Email reservations directly mentioning honeymoon — Four Seasons consistently delivers honeymoon amenities (champagne, room upgrade, late checkout) for booked-direct stays.
Adults-only?
Four Seasons Anguilla is family-friendly with a kids' programme, but the resort is large enough that the cliffside Oceanfront Villas remain quiet and adult-dominated. Couples and honeymooners are the main demographic outside the August/Easter/Christmas family peaks.
Best room type?
The One-Bedroom Oceanfront Villa with Pool is the essential Four Seasons Anguilla honeymoon experience — Wearstler-designed standalone villa on the cliff with a private infinity plunge pool cantilevered over Barnes Bay. For ultra-luxury, the Beachfront Residences offer per-bedroom rentals with private chef and butler.
How to get there?
All international flights connect via Sint Maarten (SXM). From SXM, choose between a 25-minute public ferry from Marigot ($25/person plus taxi to AXA Clayton Lloyd) or a 7-minute private charter via Tradewind, Anguilla Air Services, or Calypso Charters ($300-700 per couple). Four Seasons arranges all ground transfers from AXA.
Same Vibe, Different Destination
