Anguilla, renowned for its pristine beaches, luxurious resorts, and exclusive charm, consistently ranks among the top 25 islands in the Caribbean, Bermuda, and the Bahamas. This small island stands out by maintaining the untouched beauty and relaxed vibe reminiscent of the Caribbean’s past.
While other Caribbean hotspots get crowded with tourists fleeing winter, Anguilla remains pleasantly tranquil. “Anguilla is never overly crowded, unlike many other nearby islands,” says Stacey Liburd, director of tourism at the Anguilla Tourist Board. This is a sentiment shared by both locals and repeat visitors who value the island’s serene beaches. However, it’s important to note that Anguilla has a particularly quiet off-season. During September and October, many resorts close, limiting accommodation options and activities. “Flights to Anguilla are available all year, but there are more options during the high season from November through April,” says David Zipkin of Tradewind Aviation.
The high season in Anguilla spans from December to April, with an influx of visitors during the holidays. Yet, as Shannon Kircher, marketing director at Frangipani Beach Resort, observes, “Even in our busy season, you’re often alone on the beach. Our version of busy is quite different.” Thus, even during peak times, visitors can enjoy a relatively quiet experience.
Late spring and early summer are ideal times to visit Anguilla. “May and June are my favorite months to travel to Anguilla,” says Kircher. “The seas are calm, the weather is almost always perfect, and it’s less crowded.” The best weather is during the dry season from December to April, with temperatures in the low 80s, perfect for beach activities and exploring the island. After the holiday rush, prices drop slightly in late January and more significantly by late April or May, as the high season winds down.
For those looking for the best deals, visiting Anguilla in the off-season, particularly in September and October, offers the lowest prices. However, this period comes with the drawback of many resorts and restaurants being closed. As a result, travelers may find that the reduced options during these months outweigh the savings. While Anguilla is accessible year-round, the best times to visit for a mix of good weather, fewer crowds, and available amenities are during the late spring and early summer shoulder seasons.
