Anguilla Events, Season by Season, and What to Do Each Month. Focus keyword: anguilla events.

Anguilla’s year turns on a handful of dates worth planning a trip around: Moonsplash at the Dune Preserve in March, Festival del Mar in Island Harbour at Easter, the Anguilla Culinary Experience from April 28 to May 2, 2027, Anguilla Day on May 30, and the Summer Festival boat races from mid-July into early August, with Christmas and New Year the busiest weeks of all. Between them, the weather decides the days: dry, bright winters for boat days to the cays, the shoulder months of May and November for near-perfect weather and more choice of houses, and a quiet summer and autumn with the warmest sea of the year. Below are the events season by season and what we would do each month, with a house for each season from our Anguilla villa rentals.

Anguilla events at a glance

Dates for 2027 are confirmed only where the organizers have announced them; for the rest we give the usual timing and the 2026 dates, and we confirm the program for your week when it is published. For temperatures, the sea and the high season month by month, see the best time to visit Anguilla.

December to February: the festive weeks and the first races

The dry season, and the island at its fullest from mid-December. The events are the holidays themselves and, from February, the boat races, Anguilla’s national sport, sailed off the beaches by the island’s open racing boats.

December

84°F by day, 73°F at night · sea 81°F · dry

The festive season from mid-month. National Heroes and Heroines Day, a public holiday, falls on December 18 in 2026. On New Year’s Eve 2025 many of the resorts held their own fireworks, and the community displays were at Sandy Ground and in The Valley. We would spend the days on the beach at Shoal Bay East or Meads Bay and keep Christmas dinner at the villa, with the chef.

January

84°F / 73°F · sea 79°F · settled and sunny

The island grows quieter after New Year, which makes January the month for a boat day to Prickly Pear Cays or Sandy Island, snorkeling at Little Bay and a long lunch on the sand. At Road Salt Pond, herons and egrets begin nesting.

February

84°F / 73°F · sea 79°F · among the driest months

The boat racing season opens: in 2026 the first race was on February 15 at Sandy Ground. Presidents’ Day is Monday, February 15, 2027, and that week books early. On the quieter days, a round of golf at Aurora Anguilla, above Rendezvous Bay.

Villa Le Bleu

Little Harbour · 11 bedrooms · sleeps 20

Two residences on two and a half acres at the water’s edge in Little Harbour, with two private beaches, an infinity pool and a second pool, a floodlit tennis court and a cinema. The harbor’s calm water suits the youngest swimmers, and Shoal Bay is fifteen minutes away by car. Over Christmas and New Year it asks for seven nights.

Staff and service: fully staffed, with a full-time private chef and an assistant chef, a butler, an estate manager, a guest relations manager and daily housekeeping with turndown.

March to May: Moonsplash, Easter, the Culinary Experience and Anguilla Day

The busiest stretch of the calendar, still in the dry season. Easter falls early in 2027, on March 28, so Festival del Mar and the Easter holidays come in the same month as Moonsplash.

March

84°F / 73°F · sea 79°F · dry and bright

Moonsplash, Bankie Banx’s reggae and roots festival at the Dune Preserve on Rendezvous Bay, is held over a full-moon weekend, usually in March: March 5 to 8 in 2026. Easter weekend brings Festival del Mar to the fishing village of Island Harbour, with a deep-sea fishing tournament, boat races, an ocean swim and seafood stalls; Good Friday is March 26 and Easter Monday March 29, 2027. Sea turtles start to come ashore to nest, a season that runs to November.

For Moonsplash we look first at Rendezvous Bay, a few minutes from the Dune Preserve; for Festival del Mar, at Shoal Bay and the east end, the side of the island where Island Harbour is.

Round Rock Estate

Rendezvous Bay · 6 bedrooms · sleeps 12

A few minutes from the sand of Rendezvous Bay, the beach of the Dune Preserve, with St Martin across the water. Six bedrooms with their own bathrooms, each with a king bed that can be split into two singles, which suits a group of friends as well as a family.

Staff and service: daily maid service seven days a week, a welcome basket and our 24/7 concierge.

Villa Alkera

Shoal Bay · 5 bedrooms · sleeps 10

In Shoal Bay, a private residential area on the north-east coast, with a pergola and an infinity pool above the sea. All five bedrooms have their own bathroom and a view of the sea, which makes it an easy house for two or three couples, or a family with grown children.

Staff and service: a dedicated villa manager, a butler, daily housekeeping and breakfast every morning, with our 24/7 concierge; an all-inclusive stay can be quoted.

April

86°F / 75°F · sea 81°F · the season eases

After Easter the season eases and the choice of houses widens. On April 28 the Anguilla Culinary Experience begins: five days of chefs’ dinners at resorts, restaurants and private villas, through May 2, 2027.

May

86°F / 75°F · sea 81°F · the shoulder

Near-perfect weather and more choice of houses. Anguilla Day, May 30, marks the 1967 Anguilla Revolution with a parade, the Premier’s Cup boat race and fireworks at Sandy Ground; when it falls on a weekend the holiday moves, as in 2026, when it was marked on Monday, June 1. Whit Monday is May 17 in 2027; in 2026 it brought an A-class race to Meads Bay, and the Anguilla Regatta, a small sailing race from St Maarten to Road Bay, was held on May 23 and 24 in 2026.

June to August: the Summer Festival and the boat races

Hurricane season opens on June 1, but its peak comes later, from mid-August to mid-October. Summer is warm, with the sea at 82°F, and the island’s own calendar is at its fullest: the races move to Meads Bay and Crocus Bay in June, and the Summer Festival fills late July and early August.

June

88°F / 77°F · sea 82°F · the quiet season begins

In 2026 the June races were at Meads Bay, including West Fest, and at Crocus Bay for the King’s Birthday holiday. Mornings for the water and a boat to the cays; the hottest hours at the villa, with lunch in the shade.

July

88°F / 77°F · sea 82°F · warm sea

The Summer Festival begins: in 2026 it ran from July 10 to August 9, with pageants, calypso and races building towards August. Early July also brings the John T Memorial cycling race, held for the 25th time in 2026.

August

88°F / 77°F · sea 82°F · the festival week

The heart of the festival. August Monday, August 2 in 2027, starts with J’ouvert at dawn, then a boat race from Sandy Ground round the island and one of the biggest beach parties in the region. August Thursday, August 5, takes the race to Meads Bay, Constitution Day follows on August 6, and the week brings the Grand Parade of Troupes; the Champion of Champions race at Sandy Ground closes the festival on the Sunday after.

The Beach House

Meads Bay · 8 bedrooms · sleeps 16

On Meads Bay, with an infinity-edge pool, a tennis court, a children’s play area, and rowing boats and paddleboards for the calm summer sea. For most of the year it asks for four nights.

Staff and service: fully staffed, with private chefs and an assistant chef, a property manager, daily maid service, food and beverage staff from 7 a.m. to 11 p.m. and a member of staff on hand 24 hours a day.

The Beach House sits on Meads Bay, where the August Thursday race and the June races were held in 2026.

September to November: the quiet months

The heart of hurricane season, from mid-August to mid-October, with the warmest sea of the year and the island at its most private. It is a time for a long stay at the villa rather than for events; when you book these weeks, ask us about the cancellation terms.

September

88°F / 77°F · sea 84°F · the wettest stretch begins

The quietest month. Days at the villa, the spa brought to the house, and the beaches almost to yourselves. Sea turtles are still nesting.

October

88°F / 77°F · sea 84°F · the warmest sea

The warmest water of the year, for swimming rather than sailing. Shorebirds and waterfowl return to the salt ponds for the winter, and Road Salt Pond is the place to see them.

November

86°F / 75°F · sea 82°F · the shoulder returns

Hurricane season ends on November 30, and the island prepares for the winter. Thanksgiving week, November 25 in 2027, opens the season.

How we plan a stay around the calendar

• The house, then the event. For Moonsplash we look first at Rendezvous Bay, for Festival del Mar at the east end near Island Harbour, and for the Summer Festival at Meads Bay, or close to Sandy Ground.
• The days that move. When a public holiday falls on a weekend, Anguilla marks it on a weekday, and the race goes with it. We confirm the dates for your week when the government publishes the 2027 holidays.
• The table, the boat and the driver. On event days we book the restaurant, the boat and the car ahead, and stock the house before you land.
• When to book. 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.

Anguilla events: your questions answered

More Anguilla guides

• Anguilla villa rentals
  Our collection, with a shortlist in 24 hours.
• The best time to visit Anguilla
  The weather and the sea month by month, and when to book.
• The best things to do in Anguilla
  Beaches, boats, golf and the island’s tables.
• The best beaches in Anguilla
  Which beach for which day, and the villas on each.
• Where to stay in Anguilla for the holidays
  The four areas for Christmas and New Year.
• How to get to Anguilla
  The nonstop flights and the boat from St Martin.

Updated October 2026. Sources: festivals and boat racing as the national sport from the Anguilla Tourist Board; Moonsplash 2026 from Anguilla Focus; Festival del Mar from The Anguillian; the Culinary Experience 2027 from the festival; Anguilla Day 2026 from the Government of Anguilla; 2026 public holidays from the Government of Anguilla; the 2026 race calendar from Anguilla Focus; Summer Festival 2026 from Anguilla Focus and the festival organizers; the Regatta from Caribbean Sailing; New Year’s Eve 2025 from Anguilla Focus; Road Salt Pond from the Caribbean Birding Trail; nesting turtles from WIDECAST; hurricane season peak from the National Hurricane Center; temperatures from Weather2Travel. Villa details are from our listings.