Optimal Seasons to Explore Anguilla: Avoid Crowds, Enjoy Perfect Weather, and Experience Top Sailing

Planning to visit the Caribbean island of Anguilla? Here are the best times to go.

Stunning beaches, incredible resorts, and the undeniable mystique of exclusivity have made the tiny island of Anguilla a fixture on iBestTravel‘s list of 25 Favorite Islands in the Caribbean, Bermuda, and the Bahamas for several years running. The best part of Anguilla? It preserves the untouched beauty and laidback 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, director of tourism at the Anguilla Tourist Board. It’s a sentiment repeated by many locals and return visitors: this island isn’t one where you’ll ever have to worry about elbowing your way down the beach.

Understanding Anguilla’s Seasons

Anguilla’s seasons fall into three main categories:

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

Before planning your trip 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 of Tradewind Aviation, which brings flights to the island from 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 Anguilla for Smaller Crowds

December 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 Anguilla for Good Weather

For ideal weather, visit Anguilla during the drier months, which are December through April. While it’s warm in Anguilla year-round, with temperatures hovering in the low 80s most of the year, December through April are slightly balmier and much sunnier. It’s the perfect time to enjoy beach hopping and all that the island has to offer.

Best Times to Visit Anguilla for Lower Prices

After the holiday-season travelers pack their bags, prices decrease slightly in late January, but they drop significantly during the shoulder season. Prices will subside by late April or May as seasonal residents and travelers returning home to escape cold winters lead to a quieter, more affordable Anguilla.

Travelers can enjoy even lower prices during Anguilla’s off-season in September and October. However, off-season often leads to larger resorts and many restaurants shutting entirely, which could make a stay less enjoyable compared to other times of the year.

Best Times to Visit Anguilla for Sailing

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

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

Rough seas and often-passing storms complicate the sailing experience during the Atlantic hurricane season, which stretches from June through November and peaks in September and October. While sailing remains possible during these months, plans become much more susceptible to last-minute weather alterations.

Best Times to Visit Anguilla for Diving

The pleasant weather that defines December through April also makes this the ideal time to enjoy Anguilla’s stunning diving sites. While PADI asserts that “excellent visibility is the norm” in these waters, this period is particularly advantageous for diving at the renowned wreck site, El Buen Consejo, or at any of the protected marine parks enveloping the island.

Rainfall is minimal in February and March, resulting in optimal underwater visibility and calmer currents. Moreover, there’s no need to wear a wetsuit while diving in Anguilla; even during the slightly cooler months, average water temperatures remain in the low 80s.

Best Times to Visit Anguilla for Festivals

May tends to be a festive season on the island, marked by two annual celebrations that could enhance a memorable vacation in Anguilla. In the middle of May, the island hosts the Anguilla Regatta, considered one of the finest regattas in the Caribbean. Anguilla Day on May 30 commemorates the island’s independence from St. Kitts and Nevis and is celebrated with parties, boat races, parades, and much more.

Anguilla also celebrates its annual summer carnival, known as the Anguilla Summer Festival, featuring an exciting lineup of parades, parties, concerts, and boat races that stretch from late July to early August. The first Monday in August, referred to as “August Monday,” represents the peak of the festivities. These events offer visitors a unique opportunity to engage with the island’s culture and traditions firsthand. Keep in mind that sometimes these celebrations lead to temporary shop and restaurant closures.

Worst Times to Visit Anguilla

September and October mark the peak of the Atlantic hurricane season, resulting in a significant decline in tourism across Anguilla. During these months, many resorts, hotels, and restaurants may close entirely, providing a distinctly different experience than during the rest of the year.

Although a few smaller hotels may remain open, the closure of most restaurants and larger resorts can hinder visitors’ ability to fully appreciate the richness of the island at this time. Locals suggest that the off-season is gradually changing, but for now, it may be best to avoid visiting during September and October to truly experience all that Anguilla has to offer.