For some people, kicking back for a week at a beautiful island resort is the ideal getaway. For others, a Caribbean holiday is more complete when it allows them to get a taste of the island’s culture—to feel like they’ve genuinely experienced and connected with that exotic locale. While most islands in the Caribbean have a distinct native culture to share, some—whether it’s because of difficult geography, limited infrastructure, or even safety issues for travelers—make it difficult for visitors to connect with it outside of their resorts. Anguilla is not one of those places.
For starters, Anguilla is Spanish for “eel” and was given that name by Christopher Columbus, who thought that the island, from a distance—given its long, flat topography—looked like an eel swimming on the surface of the water. That makes the island very easy to navigate; and with no crime issues to keep them relegated to their resorts, visitors will want to venture away from those confines to enjoy some island hospitality at a handful of popular beach bars. These vibrant establishments offer flavorful sips and plenty of sun and sand during the day, but transform into energized dance clubs and live music venues at night.
Along the coast of the Sandy Ground region on the north central side of the island, a number of Anguillan hotspots can be found. These include The Pumphouse, a dwelling that was once pivotal to the harvesting of the island’s salt from a nearby pond but is now a favorite hangout for natives and features an impressive array of Caribbean rums; Elvis’s Beach Bar, an island haunt that features a salvaged-wooden-boat-turned-bar and serves Mexican food and stiff drinks; and Sandbar, a seaside eatery that serves refined small plates and cocktails that include a hibiscus martini and a jalapeno pineapple mojito.
Those looking for a more raucous night out, one filled with reggae and rum punch, will want to venture to the south side of the island where musician Bankie Banx—Anguilla’s answer to Jamaica’s Bob Marley—has built the Dune Preserve, a sprawling complex of bars and covered seating areas built from ships that have run aground, which is home to the Caribbean’s longest-running independent music festival each March.
Best of all, because the island is not visited by cruise ships and does not offer a casino of any type, these most popular destinations for fun and entertainment are ones visited by both locals and visitors. That confluence of people provides a far more enriching experience for travelers, especially those who prefer to not be surrounded only by other tourists.
Of course, such a feature is appealing to those who like the idea of calling Anguilla home—or at least like the idea of making Anguilla their second home. For that particular crowd, the new private residences at the Four Seasons Anguilla are an ideal solution. Not only do they offer a wide range of styles and sizes—everything from one-bedroom retreats to five-bedroom villas—they also allow their owners to take advantage of all of the resort’s amenities. What’s more, their location is ideal for those who wish to venture out to Sandy Ground or the Dune Preserve. But then, given the small size and flat topography of the island, even the most far-flung of Anguilla’s enticing destinations is never too far away.