The best time to visit Anguilla for winter sun, island festivities and escaping the crowds

With weather being relatively consistent, Anguilla’s year-round appeal means that choosing when to visit the island is often more a matter of your personal travel style, activity preferences and budget.

Hotels on the island largely break down a year into five distinct seasons: fall, Festive Season, winter, summer and off-season, when the island noticeably quiets down. Trying to decide which time of year is right for you? Here’s what to expect season by season in Anguilla.

Anguilla's weather means endless summer

The island’s proximity to the equator means the sunset shifts almost indiscernibly as the year carries on, so there's a constant dose of daylight hours in summer and winter. Temperatures typically vary by less than 10°F throughout the year, hovering around the low 80s in winter and edging towards the high 80s in the summer months.

Compared with more tropical Caribbean outposts, Anguilla is a relatively dry island, receiving an average of about 35in of rain per year. Even during the wetter months, rainfall tends to be fleeting, with brief localized downpours followed by radiant sunshine.

For a lower-priced holiday-season escape, book November to mid-December

While winter is moving into most parts of the US, Anguilla is just beginning to awaken after a two-month slumber. Resorts on the island largely reopen around the first of November, and restaurants follow suit. Weather-wise, temperatures usually hover around the mid 80s, with remnants of summer’s humidity fading away.

Rain can be unpredictable during this time, with a number of days bringing momentary downpours followed by sizzling daytime sun. Tourism is on the rise again, with visitor numbers slowly increasing as the month wears on towards Thanksgiving week.

The seas, constantly warm from the ever-present sun, begin to shift as winter approaches, leaving behind the placid conditions of summer and bringing the fickler conditions of winter. For travelers in search of a pre-holiday escape, it's great to be on the island ahead of the Festive Season, as hotel prices increase noticeably in mid-December.

Festive Season runs from mid-December through early January

Anguilla’s buzziest period, Festive Season runs from mid-December through the first week of January, with mega yachts anchoring in Meads Bay and beyond as the holidays draw near. Accommodation pricing reaches its peak, often with minimum lengths of stay, as travelers migrate south for the winter to celebrate the holidays.

While winter is in full swing in the northern hemisphere, Anguilla’s temperatures rarely drop below the low 80s, with relatively little humidity as the “Christmas winds” whistle through. Given Anguilla’s Caribbean locale, the sun sets around 5:30pm, even on the shortest days of the year, which means ample time for soaking up the sun on the world-famous beaches.

Hotels and restaurants are bustling during the Festive Season, with an increase in live music and a number of luxury hotels hosting special events to ring in the New Year. Expect fireworks, guests-only resort parties and a more glamorous feel across the island. Many hotels are booked a year in advance with repeat visitors, and dinner reservations are a must.

Visit between January and mid-April for a quieter experience

After Festive Season draws to a close, Anguilla slowly begins to downshift. Rainfall can vary during the winter and spring seasons, with winter months bringing intermittent passing showers.

Celebrations begin to emerge as winter fades into spring: In March, Bankie Banx’ Dune Preserve hosts Moonsplash, an annual multi-day reggae festival designed to coincide with the full moon for music under the stars. During Easter weekend, Festival del Mar takes place in Anguilla’s fishing village, Island Harbour, with tented outposts serving barbecued seafood and rum punch while colorful sailboats bounce along the seafront, drawing locals, expats and tourists from all over the island.

Days slowly begin to get longer as the springtime months approach, and Anguilla’s rhythm begins to change, almost imperceptibly, as summer draws near. The island begins to embrace a more barefoot, local feel as the summer season commences.

The best time for budget travelers is mid-April through August

Summertime in Anguilla is arguably the island’s best kept secret: beautiful weather, calm seas, an increase in local festivities, quieter beaches and less-impacted restaurants – not to mention the best value for accommodations. Though many travelers discount the Caribbean in the summer months as being too hot, too humid or a combination of the two, that's not a concern in Anguilla: The summer temps begin to slowly increase from May through August, but the island remains pleasant, with warm, calm seas becoming the norm.

Boaters and water-sport enthusiasts will find the island’s summer months ideal, with lake-like conditions on the open sea perfect for standup paddleboarding, kayaking or waterskiing. With some of the year’s longest days, the sun begins to set closer to 7pm, bringing the most vibrant, colorful sunsets of the year.

For culture-seekers wanting more authentic Caribbean experiences, local events begin to come to the fore as May comes to a close. Sailboat racing, the national sport of Anguilla, takes off on May 30 for Anguilla Day, a kickstart to a summer of celebrations. Each village on the island is represented by its own hand-built boat, and islanders flock to the cliff sides and beaches to watch the races while the boats zip around the island.

Anguilla’s festivities culminate with the island’s Carnival celebration which takes place over the first week of August. Centering around August Monday (the first Monday of the month), the island hosts one of the Caribbean’s biggest beach parties in Sandy Ground, complete with sizzling BBQ stations, a rotation of local music, and rum punches being doled out by the dozens.

September and October are best for avoiding the crowds

The end of August signals the end of the season for many hotels and restaurants on the island, and some properties close down for a two-month hiatus, using the time for renovations and a break before restarting in November. Boats are often moved to safe harbor or pulled out of the sea entirely for the off-season.

While hurricane threats are undoubtedly at their peak during these two months, many years the island remains storm-free, with days of hot sunshine and beaches that are barren but for palm trees and shuttered beach shacks.

A small collection of accommodations and a few local restaurants remain open for visitors looking for the ultimate low-key escape. Generally speaking, visitors are cautioned to avoid September and October given storm threats and lack of facilities though visitors in search of absolute serenity may find their own peaceful enclave during the island’s quietest period.

January

Anguilla is at peak-glam as visitors ring in the New Year, with fireworks and parties across the island. Daytime temps remain in the low-80s in winter, with some cool evening breezes and the occasional shower passing through.
Key events: New Year’s Eve

March

Balmy winter weather continues throughout March. Whale-spotting opportunities, though rare, are most frequent from March to April, during the annual migration.
Key Event: Moonsplash

April

April marks a seasonal shift in Anguilla, when the island's hotels largely enter their summer rate period around mid-month.
Key Event: Festival Del Mar

May

The weather begins to slowly shift as summer months approach, with weather creeping into the mid to high 80s. Seas noticeably get calmer, and placid conditions become the norm – a boon for water-sports enthusiasts.
Key Events: Anguilla Day, Anguilla Epicurean Festival (beginning 2022)

June

June is generally warm and sunny, bringing the longest days of the year, temperatures around the high 80s and the fewest days of rain. Seas remain calm, making conditions perfect for boating and visiting off-island cays.

July

The warm weather continues, and humidity slightly increases as July wears on. Seas remain calm, and the island’s longer days remain a draw, with later sunsets and warmer temperatures into the evening hours. During the latter part of the month, the island begins to gear up for its annual Summer Festival in August, with some pre-Carnival festivities scheduled in late July. Expect Calypso competitions, pageants, and fêtes as the month comes to a close.
Key Events: Pre-Carnival festivities vary annually but include competitions, pageants, galas and more.

August

One of the hottest months of the year, August brings an average monthly temperature of 89°F with evenings remaining balmy. The island’s most important local festivities take place in August during the Summer Festival, when Carnival is celebrated with a week of activities and parties. August Monday (the first Monday of the month) marks one of the Caribbean’s biggest beach parties, but the week is also punctuated by smaller fêtes across the island. Sailboat races culminate on the Sunday following August Monday with the annual Champion of Champions contest.
Key Events: August Monday and Carnival celebrations, Poker Run

September

September is the beginning of a complete seasonal shift on the island, and most hotels and restaurants board up for the off-season, when hurricane threats are at their peak. Temperatures remain at their highest – in the upper 80s – and humidity notably increases.

October

The seasonal closures continue through much of October, though some resorts and restaurants begin reopening around the middle of the month as preparations commence for the new season. Temperatures remain high, and humidity continues throughout the month.

November

November marks the island’s awakening after a two-month pause, with hotels and restaurants largely reopening around the first of the month. As the weeks wear on, humidity begins to decrease, and temperatures slowly begin to drop. Statistically, rainfall is at its peak in November, though rain clouds often blow through as quickly as they arrive.
Key Events: Seasonal reopening for most hotels and restaurants

December

December is another transitional month as the island kicks into high gear. Yachts and private jets begin to descend as the Festive Season arrives, and tourism is at its peak during the holiday period toward the end of the month. Temperatures fall to the low 80s during the day, with nights cooling into the mid 70s as ‘Christmas winds’ arrive. Festive Season is practically an event unto itself in Anguilla, with properties alive with concerts, filled restaurants, and celeb-spotting.
Key Events: Festive Season

Anguilla is on our 2022 Best of Travel list. For more stories from some of the world’s most exciting destinations click here.

Safety recommendations and restrictions during a pandemic can change rapidly. Lonely Planet recommends that travelers always check with local authorities for up-to-date guidance before traveling during Covid-19.
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