Optimal Times to Explore Anguilla for Fewer Crowds, Pleasant Weather, and Amazing Sailing

With breathtaking beaches, luxurious resorts, and a captivating sense of exclusivity, the small island of Anguilla has consistently secured a spot on Travel + Leisure's list of 25 Favorite Islands in the Caribbean, Bermuda, and the Bahamas for many years. The highlight of Anguilla? It maintains the pristine beauty and relaxed atmosphere reminiscent of the Caribbean's past. Even as other destinations fill up with travelers escaping winter chills, 'Anguilla remains refreshingly uncrowded compared to many nearby islands,' notes Stacey Liburd, director of tourism at the Anguilla Tourist Board. This sentiment is echoed by locals and returning guests alike: you won't find yourself struggling for space on the beach here. Anguilla's seasons are categorized into three main types:

• Peak Season: November to April
• Shoulder Season: May to July
• Off-Peak Season: August to October

Before finalizing your travel plans to Anguilla, be aware that the island experiences a notably serene low season. Many resorts close in September and October, which can restrict lodging options and activities for visitors. 'Flights to Anguilla operate throughout the year, but you'll find more choices during the peak season from November to April,' says David Zipkin of Tradewind Aviation, which offers flights from San Juan, Puerto Rico. Continue reading to discover the ideal times to visit Anguilla for sailing, diving, and festivals — and understand why it's always an excellent spot to avoid crowds.

Optimal Times to Explore Anguilla for Fewer Crowds

From December to April, Anguilla experiences its peak season, seeing a significant rise in visitors during the holidays. However, 'Anguilla is never truly crowded — even during our busiest times, you'll often find yourself walking to the beach alone on most days. It's a different kind of busy,' notes Shannon Kircher, a longtime resident of Anguilla and marketing director at Frangipani Beach Resort, which was recognized among T+L readers' T+L Readers' Favorite Resorts in the Caribbean this year.

Crowds, even by Anguilla's standards, diminish notably in late spring and early summer. 'May and June are my top picks for visiting Anguilla as a traveler,' shares Kircher. 'The seas are tranquil, the weather is almost guaranteed to be idyllic, and it’s a bit less hectic.'

Optimal Times to Experience Anguilla for Great Weather 

For the best weather, plan your visit to Anguilla during the drier months from December to April. While temperatures are warm year-round, typically in the low 80s, December through April offer slightly milder and sunnier conditions. It’s the perfect period for beach hopping and exploring the island from the water.

Optimal Times to Visit Anguilla for Better Prices

Following the holiday rush, prices see a slight dip in late January, though not as significant as during the shoulder season. By late April or May, rates decrease further as seasonal residents and winter escapees depart, marking the beginning of Anguilla's shoulder season.

Visitors can take advantage of even lower prices during Anguilla's off-peak season in September and October. However, this period often sees many larger resorts and restaurants completely closed. As a result, potential travelers frequently weigh whether the savings justify a visit during these months.

Optimal Times to Visit Anguilla for Sailing 

Sailing is a cherished national pastime in Anguilla, serving as both a beloved hobby and a practical means of transport for many visitors arriving by boat from nearby St. Martin. Those planning a sailing adventure should target the tranquil spring months, known for their calm waters and sunny skies. 'The Caribbean generally offers consistent sailing conditions throughout the year,' states Dan Lockyer, chief commercial officer of Dream Yacht Worldwide, which provides charters to Anguilla from St. Martin. 'Smoother seas in spring make it easier to island-hop for snorkeling and visit Anguilla's offshore cays, such as Prickly Pear, for a lobster lunch.' The Atlantic hurricane season, which lasts from June to November but peaks in September and October, brings rougher seas and unpredictable storms, making sailing more challenging. While sailing during these months is still possible, plans are more likely to be affected by sudden weather shifts.

Optimal Times to Visit Anguilla for Diving

The delightful weather from December to April makes it the prime time for both sailing and experiencing Anguilla's amazing diving. According to PADI, 'excellent visibility is standard' in these waters, especially during this period, which is ideal for diving at the famous Spanish galleon wreck, El Buen Consejo, or at any of the island's protected marine parks. Rainfall is minimal in February and March, making these months particularly good for underwater visibility and calmer currents. Plus, there's no need for a wetsuit in Anguilla's waters; even in the cooler months, average temperatures remain in the low 80s.

Best Time to Experience Anguilla's Festivals 

May is a lively month on the island, featuring two annual festivities that can enhance a memorable vacation in Anguilla. In mid-May, the Anguilla Regatta takes place, renowned as one of the top regattas in the Caribbean. Anguilla Day on May 30 commemorates the island's independence from St. Kitts and Nevis, celebrated with parties, boat races, parades, and more. Additionally, Anguilla hosts its annual summer carnival, known as the Anguilla Summer Festival, featuring a vibrant schedule of parades, parties, concerts, and boat races from late July to early August. The celebration peaks on the first Monday in August, referred to as 'August Monday.' These events offer visitors a wonderful chance to engage with the island's culture and traditions. However, be aware that some celebrations may lead to temporary closures of shops and restaurants.

Least Favorable Times to Visit Anguilla 

September and October represent the peak of the Atlantic hurricane season and a noticeable drop in tourism in Anguilla. During these months, many resorts, hotels, and restaurants completely shut down, making a visit to Anguilla during this time a significantly different experience compared to the rest of the year.

While there are a few smaller hotels that remain operational, the majority of restaurants and larger resorts close down, making it difficult to fully experience the island's vibrant offerings during this time of year. Locals mention that this off-season might start to shift, but for now, it's best to avoid September and October to truly savor all that Anguilla has to offer.