Anguilla: A Vacation for Every Season

Beach Massage on Shoal Bay Beach Anguilla

Jesson & Co / MNI Alive

Release Date

Monday, November 13, 2023


Anguilla, the Caribbean's hidden gem, calls out to snowbirds with an irresistible invitation to ditch the chill of Canadian winter and embrace its endless warmth. Here, you'll discover inviting beaches, delightful weather, and a culture that's as warm as the sunshine. Anguilla isn't just a well-kept Caribbean secret; it's your ticket to luxurious resorts, unforgettable dining experiences, and a vibe that keeps folks returning year after year. So, snowbirds, whether you're all about soaking up the sun, indulging your taste buds, or seeking adventure, Anguilla has something to offer for every type of traveller. 

Of course, while Anguilla has traditionally been a premiere winter getaway, there’s so much more to see and experience all year round. Anguilla is a dynamic destination that changes with the temperature, offering new things to experience and new reasons to go, both in the peak and off-season. To highlight this diversity, we’ve spotlighted the unique virtues of each of Anguilla’s tourism windows below. Choose the one (or ones) that are right for you, and discover exactly why Anguilla is so much more than just a snowbird’s dream!

The Pre-Holiday Seasons: November to mid-December

As the chilly winds of November and December begin to sweep across North America, Anguilla offers a sun-drenched sanctuary with near-perfect weather. With temperatures hovering around a blissful 79°F to 84°F (26°C to 29°C), the island offers an ideal climate for outdoor exploration and beachfront relaxation. It is still considered the off-season in Anguilla, so the rates are cheaper and restaurants are typically in the process of re-opening.

Notably, this season brings fewer crowds, allowing visitors to savour the island's pristine beaches and top-notch dining experiences at their own pace. The unique cultural events and festivals that come alive during this period provide a glimpse into Anguilla's storied heritage, making it an enriching and immersive time to visit the island. With its clear waters teeming with marine life, water sports enthusiasts will also find November to December an excellent time for snorkelling and scuba diving. Time your visit right before the Festive Season (see below!) for some of the best deals on resorts and hotels.

he Season of Holidays: mid-December through early January

Wooden Christmas Tree

Wooden Christmas Tree, photo courtesy of the Anguilla Tourist Board

The spirit of Anguilla is on full display during its renowned Festive Season when the island blossoms with local celebrations and cultural events that are sure to infuse your trip with infectious joy.

As winter takes hold in the northern hemisphere, Anguilla remains a warm and inviting haven. The temperatures rarely dip below the low 80s, offering a respite from the cold elsewhere. The "Christmas winds" gently whisper through the island, making it an ideal place to escape the winter chill.

Live music, exclusive resort parties, and spectacular fireworks add to the island's festive charm, ensuring an unforgettable New Year's celebration. Many of the island’s grandest properties (including the Four Seasons, Cap Juluca, and Aurora Anguilla Resort & Golf Club) host can’t-miss special events. It's a time when Anguilla truly sparkles, but be sure to book your hotel well in advance and make dinner reservations – the festive spirit is in high demand!

The Season of “Quiet Luxury”: January to mid-April

Backstreet South Hill, Anguilla

Backstreet South Hill, photo courtesy of the Anguilla Tourist Board

After the vibrant Festive Season draws to a close, the island takes on a serene ambiance, providing a perfect escape from the winter blues. While there may be occasional passing showers during these months, the weather remains comfortably warm, making it an ideal time to bask in the Caribbean sun.

As winter transitions into spring, Anguilla still has much to offer adventurous guests with unique celebrations. In March, the Dune Preserve, owned by Bankie Banx, sets the stage for Moonsplash, a multi-day reggae festival where music under the stars becomes a magical experience. Easter weekend brings the lively Festival del Mar to Anguilla's charming fishing village, Island Harbour, where barbecued seafood and rum punch tantalize the taste buds, and colourful sailboats dance along the seafront, attracting locals, expats, and tourists alike.

Moreover, as the springtime months roll in, days gradually become longer, offering more sunshine to enjoy the island's beauty. Anguilla's rhythm transforms almost imperceptibly, heralding the approach of summer and a more relaxed, barefoot, and local feel. For visitors seeking a blend of tranquillity and cultural celebrations, January to April in Anguilla presents an irresistible invitation to experience the island's unique charm and evolving character.

Whether you’re escaping the chill of winter or trading warm pastures for…well, warmer pastures, Anguilla stands out as the quintessential tropical paradise, with compelling reasons to visit in every season. You can learn more about Anguilla and start planning your unique getaway by visiting

Barnes Bay, Anguilla

Barnes Bay, Anguilla, photo courtesy of the Anguilla Tourist Board

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