These Are the Best Times to Visit Anguilla for an Island Escape

Stunning beaches, incredible resorts, and the undeniable mystique of exclusivity have put the tiny island of Anguilla on the list of Travel + Leisure readers’ favorite islands in the Caribbean, Bermuda, and the Bahamas for several years running. The best thing about Anguilla? It preserves the untouched beauty and laid-back vibes of what the Caribbean used to be. 

Even as the rest of the region heats up with travelers escaping icy winters, “Anguilla is never overly crowded, as many other neighboring islands can be,” says Stacey Liburd, the Anguilla Tourist Board’s former director of tourism. It’s a sentiment repeated by many a local and return visitor: this island isn’t one where you’ll ever have to worry about elbowing your way down the beach.

Anguilla’s tourism seasons fall into three main categories:

• High Season: November to April
• Shoulder Season: May to July
• Low Season: August to October

Before booking your flight to Anguilla, keep in mind that the island experiences an unusually quiet low season. Shuttered resorts in September and October can limit accommodation options and experiences for travelers. “Flights to Anguilla are offered year-round, but more options exist during the high season, November through April,” says David Zipkin, co-founder and chief commercial officer of Tradewind Aviation, which operates flights between the island and San Juan, Puerto Rico. 

Read on to learn about the best times to visit Anguilla for sailing, diving, and festivals—and why it’s always the perfect place to escape crowds.

Best Times to Visit for Smaller Crowds

November through April is Anguilla’s high season, with a marked increase in travelers over the holidays. However, “Anguilla is never busy—even in our busy season, you’re walking to the beach by yourself most days. It’s a different idea of what busy means,” says Shannon Kircher, longtime Anguilla resident and marketing director at Frangipani Beach Resort. The crowds, even by Anguilla’s standards, die down significantly in late spring and early summer. “May and June are my personal favorite months to visit Anguilla as a traveler,” says Kircher. “The seas are calm, the weather is almost guaranteed to be perfect, and it’s a little bit less busy.”

Best Times to Visit for Good Weather 

For ideal weather, visit Anguilla during the drier months. While it’s warm in Anguilla year-round, with temperatures hovering in the low 80s most of the year, December through April are slightly more balmy and much sunnier. It’s the ideal time to visit for beach hopping and enjoying the island from the water.

Best Times to Visit for Lower Prices

After the holiday season, prices decrease slightly in late January, though nothing like they do come the shoulder season. Rates will drop by late April or May as seasonal residents and travelers escaping cold winters head home and Anguilla’s shoulder season unfolds.

Visitors can enjoy even lower prices during Anguilla’s off-season, from August to October. Note, however, that off-season also means the island’s larger resorts and many restaurants shutter entirely. Prospective travelers often decide that visiting Anguilla during these months may not be worth the savings.

Best Times to Visit for Sailing 

Sailing is Anguilla’s beloved national sport, both a constant pastime and a necessity on this tiny island, as many visitors still arrive by boat from neighboring St. Martin. 

Travelers planning a sailing trip should aim for the calmer spring months, when still waters and sunny skies are the norm. “The Caribbean has pretty steady sailing conditions year-round,” says Dan Lockyer, former deputy CEO of Dream Yacht Worldwide, an outfit offering charters to Anguilla out of St. Martin. “Calmer seas in the spring make it easier to hop from beach to beach for snorkeling and to visit Anguilla’s off-shore cays, like Prickly Pear, for a lobster lunch.”

Rougher seas and frequently passing storms make the Atlantic hurricane season more challenging for sailing in the Caribbean. Hurricane season stretches from June through November, but peaks in September and October. While sailing isn’t out of the question during these months, plans are much more susceptible to last-minute weather changes.

Best Times to Visit for Diving

The pleasant weather that makes December through April the ideal time for sailing also makes this the best time to enjoy Anguilla’s incredible diving scene. While PADI says “Anguilla’s dive conditions are generally favorable year-round,” December through April is the best time to dive at the island’s storied Spanish galleon wreck site, El Buen Consejo, or at any of the protected marine parks that encircle the island. 

Rainfall is at its lowest in February and March, making these months the best for underwater visibility and calmer currents. And there’s no need to don a wetsuit for diving in Anguilla; even during the slightly cooler months, average water temps hover in the low 80s.

Best Times to Visit for Festivals 

May tends to be a festive season on the island, with two annual celebrations that could bookend a memorable vacation in Anguilla. In May, the island celebrates the Anguilla Regatta, considered among the best regattas in the Caribbean. Anguilla Day at the end of the month marks the island’s independence from St. Kitts and Nevis and is just as lively, with parties, boat races, and parades, among other events.

Anguilla celebrates its annual summer carnival, also known as the Anguilla Summer Festival, with a packed itinerary of parades, parties, concerts, and boat races stretching from late July to early August. The first Monday in August, known as “August Monday,” is the height of the celebration. These festivities are a memorable way for visitors to experience the island’s culture and traditions first-hand. Just note that they sometimes lead to temporary shop and restaurant closures.

Worst Times to Visit 

September and October mark the height of the Atlantic hurricane season and a distinct decline in tourism in Anguilla. Many resorts, hotels, and restaurants close up entirely in September and October; visiting Anguilla during these months is a markedly different experience than it would be the rest of the year. Visitors will find a handful of smaller hotels that remain open, but with most restaurants and larger resorts closed, it can be challenging to truly experience the richness of the island this time of year.