Although the Caribbean Sea is peppered with several picturesque islands, Anguilla is in a league of its own. As a destination of many cultures and unique experiences, Anguilla offers a year-round getaway for those planning a destination wedding, tropical honeymoon, or an impromptu holiday filled with white sand and turquoise waters. Each month, Anguilla celebrates a particular “pillar” that highlights the island’s various attractions including Extraordinary Eats, Health & Wellness, Adventure, and Romance. With these pillars in place, there’s guaranteed to be a time of year that caters to every traveler.

Before visitors even begin to explore the island, they’ll immediately be welcomed by a sense of Anguilla’s friendly spirit. Just as the national anthem speaks of the country being “proud, strong, and free,” the locals are proudly Anguillian. “We are a resilient, caring, warm, friendly, and community-oriented people with a long tradition of hospitality,” says Jameel Rochester, Acct. Manager of Corporate Affairs and Asst. Manager of Destination Experience at the Anguilla Tourist Board.

“An interesting fact about Anguilla is that the Rain God, Juluca, named Anguilla ‘Rainbow City’ because a rainbow can be seen every day,” he continues. “Anguilla is the most northerly island in our region and owns 200 miles of uncharted waters. We are also surrounded by seven breathtaking off-shore destinations, which we call our Cays. These cays – like Prickly Pear, Scilly Cay, and Sandy Island to name a few – are like a destination within a destination. A short boat ride over to these islands takes you to the experience of a lifetime. Three of our cays currently house a restaurant that offers seafood delicacies as well as traditional fare.”

Along with venturing through the island’s cays, visitors will have no shortage of activities to fill their itineraries. There are 33 powdery white sand beaches, and Anguilla is home to the best hotels and restaurants in the region. “One of our most iconic landmarks is the Arch, located on the western part of the island,” Jameel shares. “Another must-see attraction, filled with artifacts and documents that illustrate our rich history and culture, is our Heritage Museum.”

Since guests are treated like family as soon as they arrive, “living like a local” is part of the quintessential Anguilla experience. Nights may be filled with bar-hopping, during which tourists can sample the island’s signature drinks. Dining out on The Strip in The Valley also allows visitors to try Anguilla’s famous food trucks and BBQ joints. To work off the indulgences, days can be spent at the Greg Norman designed championship golf club, the Anguilla Tennis Academy, or taking to the sea for a variety of watersports from kite surfing to scuba diving.

For those considering a destination wedding, Anguilla sets the stage for any type of wedding a couple envisions. Plan a sunrise pre-wedding photo shoot; a sunset ceremony on the beach; or an over-the-top wedding reception at a luxurious villa. The island provides the most extraordinary backdrop for everything from private elopements to guest lists of 250-plus.

Should couples opt to visit Anguilla on their honeymoon, Jameel recommends Anguilla by Sea for the ultimate date night, which includes a romantic sunset cruise while sipping champagne. A bonfire for two on the beach can also be arranged, along with candlelight dining under the stars.

“Imagine arriving at a remote beach or cay with a private dinner arranged to your desire,” says Jameel. “Having a private chef cook your favorite meals while enjoying the sound of the waves breaking against our shores. This intimate setting is an ideal representation of a beyond extraordinary experience.”

>Written By: Lauren Malamala

Photography: Enrique Vega Photography