Haute Retreats Names Anguilla a Signature Caribbean Destination for Winter 2026-27

Virtuoso ranks Anguilla the Caribbean's top festive destination, the island has just had a record first half for visitors, and new nonstop flights reach it from the U.S. Northeast this winter. The company's Anguilla collection numbers 56 villas across six of the island's beaches.

Haute Retreats, the luxury villa and concierge company representing more than 2,400 villas, mansions and private estates across 83-plus destinations, has named Anguilla one of six signature destinations in its Caribbean villa collection for winter 2026–27, alongside Turks and Caicos, St. Barts, Barbados, the Dominican Republic and St. Martin. The company's Anguilla villas number 56, from Meads Bay and Barnes Bay at the West End to Long Bay, Rendezvous Bay, Little Harbour and Shoal Bay East, and the designation comes as the island moves to the front of the Caribbean holiday market.

Anguilla at a glance, winter 2026–27: Virtuoso ranks Anguilla third worldwide and first in the Caribbean for festive travel (Dec. 15–Jan. 7). Stayover arrivals rose 19.9% in the first half of 2026, with U.S. travelers making up 73.8% of the total. Haute Retreats offers 56 villas on six beaches and advises booking Christmas, New Year and Easter nine to 12 months ahead; holiday minimum stays typically run 10 to 14 nights. Most guests arrive via St. Maarten and a 25-minute private boat, and from mid-December BermudAir's AnguillAir flies nonstop from Boston, Newark and Baltimore-Washington.

The Caribbean's festive leader

Virtuoso's festive travel rankings, presented at the network's Travel Week in Las Vegas in August, place Anguilla third among countries worldwide for travel between Dec. 15 and Jan. 7. Only the United States and Mexico rank higher, and no other Caribbean destination does; West End, Anguilla, is No. 8 among individual destinations. Across Virtuoso's network, festive bookings have risen 65% and sales 56% against the same point in 2025. The Global Travel Collection's 2026 trends report, released July 1, reaches the same conclusion from a second network: the Caribbean leads luxury holiday bookings, and Anguilla is among its top destinations.

The visitors are already arriving. Anguilla welcomed 81,907 stayover visitors in the first half of 2026, up 19.9% on the same period of 2025, according to the Anguilla Statistics Department, and travelers from the United States accounted for 73.8% of them.

Easier to reach this winter

Most Haute Retreats guests reach Anguilla through St. Maarten, followed by a 25-minute private boat crossing. From mid-December, BermudAir's AnguillAir service also flies nonstop to the island's Clayton J. Lloyd International Airport twice a week from Boston and from Newark, and weekly from Baltimore-Washington, with connections via Providenciales from Tampa and, starting Dec. 19, from Toronto.

The collection

The company's Anguilla villas run from beachfront family houses to estates built for several generations at once. Most include a private chef, a butler and daily housekeeping, with the services at each villa confirmed before booking; every stay includes the company's 24/7 concierge. Among them are Nevaeh, a gated, nine-bedroom estate on nearly half a mile of Long Bay beachfront, with a private chef and butler; Villa Le Bleu, a fully staffed villa on Little Harbour, where the water is calm enough for the youngest swimmers; and ÀNI Anguilla, an all-inclusive private resort let to a single group.

Booking the holidays

The company's published guidance for Anguilla is to book Christmas, New Year and Easter nine to 12 months ahead, and January through March six to nine months ahead; shoulder and summer dates can often be confirmed within 60 days. Over Christmas and New Year, minimum stays typically run 10 to 14 nights.

"Anguilla has earned its place the way it does everything, quietly," said Sabrina Piccinin, Founder and CEO of Haute Retreats. "There is no cruise port, the beaches are long, and the best villas are built to hold a whole family at once. Virtuoso's ranking puts a number on what our guests already tell us: when they want a Caribbean Christmas that feels private, Anguilla is the island they ask for by name."

Travel advisors and families can request winter 2026–27 availability in Anguilla, along with the company's wider collection of Christmas and New Year villas, through its concierge team at [email protected] or +1 888 279 6444.

About Haute Retreats

Founded in 2016, Haute Retreats is a luxury villa rental and concierge company representing more than 2,400 villas, mansions and private estates across 83-plus destinations worldwide. Its fully staffed collection includes a private chef, villa manager and daily housekeeping in residence; across the wider portfolio, private chefs and additional staff can be arranged at additional cost, alongside drivers, yacht charter, private jet arrangements and bespoke experiences, with a 24/7 concierge desk on every stay. The company is ASTA-accredited, a three-time Luxury Lifestyle Awards winner (2024–2026) and a 2026 Condé Nast Traveler Readers' Choice nominee. Haute Retreats holds a 5.0 rating on Trustpilot, and 80% of its guest families return.

Media Contact

Angelica, Haute Retreats, 1 3054321731, [email protected], https://hauteretreats.com

SOURCE Haute Retreats