The Best Time to Visit Anguilla

The best time to visit Anguilla is December to April, when the island has its most settled sunshine, calm water on the west-end beaches and its fullest calendar, with Christmas and New Year at the peak. May and November bring almost the same weather and more choice of villas, and June to October is the quiet, greener season, inside the Atlantic hurricane season, which runs from June 1 to November 30. For the holidays, book nine to twelve months ahead. See our Anguilla villa rentals.

Anguilla month by month

The island is warm all year: daytime highs run from 84°F in winter to 88°F in summer, and the sea from 79°F to 84°F. What changes is the rain, the wind, the calendar and the choice of houses. February and March are the driest months; September to November the wettest.

December to April: the high season

This is the Anguilla most guests picture: long days on the west-end beaches, calm water for snorkeling at Little Bay and Shoal Bay, boat days to the cays and dinners on the sand. The holidays are the peak. In August 2026 the Virtuoso travel network ranked Anguilla third in the world and first in the Caribbean for festive travel, from December 15 to January 7, behind only the United States and Mexico; West End, Anguilla, was No. 8 among individual destinations. The island welcomed 81,907 stayover visitors in the first half of 2026, 19.9% more than a year earlier, and 73.8% of them came from the United States, according to the Anguilla Statistics Department.

Anguilla is one of our six signature Caribbean destinations for winter 2026–27, with Turks and Caicos, St Barts, Barbados, the Dominican Republic and St Martin. It is also when the houses go first. We suggest booking Christmas, New Year and Easter nine to twelve months ahead, and January to March six to nine months ahead; shoulder and summer dates can often be confirmed within 60 days.

May and November: the shoulder

May has the weather of April with fewer visitors, and November the calm before the season, with Thanksgiving week at the end of the month. Both are good months for couples and for families who want a particular house: the villas that are taken months ahead for the winter often have dates.

June to October: the quiet season

Summer is hot and still, the sea is at its warmest and the island is at its most local, with the Summer Festival from late July. It is also the Atlantic hurricane season, which peaks from late August to October. If you travel then, ask about the cancellation terms of the house before you book and consider travel insurance; your specialist advises on the weeks.

The festivals worth planning around

• Moonsplash, the reggae festival at Bankie Banx’s Dune Preserve on Rendezvous Bay, usually in March.
• The Summer Festival, from late July into early August around August Monday: parades, music and the boat races, Anguilla’s national sport.
• The festive season, which Virtuoso measures from December 15 to January 7, when the island is at its fullest and the villas ask for longer stays.

When to book

Over Christmas and New Year most of the houses we checked in October 2026 ask for seven nights: ÀNI Anguilla from December 18 to January 10, Villa Sand from December 21 to January 3, and Villa Le Bleu and The Beach House over the two holiday weeks. Some of the largest estates are taken as a fortnight.

Three villas for the high season

Villa Nevaeh

Long Bay · 9 bedrooms · sleeps 18

A gated estate directly on Long Bay, with a heated infinity pool, a tennis and basketball court, a home theater and a gym. It can also be taken with five to eight bedrooms.

Staff and service: fully staffed, with a private chef, a butler and maid service, and full breakfast included.

The Beach House

Meads Bay · 8 bedrooms · sleeps 16

Directly on Meads Bay, with an infinity-edge pool, a tennis court, a children’s play area, and rowing boats and paddleboards at the water. Restaurants are a walk along the sand.

Staff and service: fully staffed, with private chefs, a property manager, daily housekeeping and a member of staff on hand around the clock.

ÀNI Anguilla

Above Little Bay · 10 bedrooms · sleeps 20

A private resort for one group on the cliffs above Little Bay: two villas side by side, each fronted by its own pool, with a gym, a spa treatment room, a tennis court and a four-minute walk down to the cove.

Staff and service: all-inclusive and fully staffed, with up to twenty staff around the clock; meals, drinks, up to six spa treatments a day and the airport transfers are part of the stay.

More Anguilla guides

• Anguilla villa rentals
  Our collection, beach by beach, with a shortlist in 24 hours.
• How to get to Anguilla
  The new nonstop flights and the boat from St Martin.
• Where to stay in Anguilla for the festive season
  Little Bay, Long Bay or the east end.
• The best things to do in Anguilla
  Boats, beaches, music and the island’s tables.

The best time to visit Anguilla: your questions answered

Updated October 2026. Temperatures are monthly averages from Weather2Travel; festive ranking from Virtuoso, reported by Caribbean Journal; visitor figures from the Anguilla Statistics Department, reported by TravelDailyNews.