The capital of Long Island, Clarence Town is home to just under 100 people, so on any given day, visitors may outnumber the locals. One main road traverses the island, which is over 70 miles long, and two different worlds unfold on either side. The eastern edge is the wild side, where Atlantic winds rustle the palm trees that frame secluded coastline, coves and caves. Explore Hamilton Cave, where Lucayan Indians lived centuries ago, and peer into Dean’s Blue Hole, one of the world’s deepest blue holes at over 660 feet.

With some of the most celebrated beaches in the Caribbean, Anguilla has the added bonus of being off the beaten path, with plenty of room to relax on the soft sands of Sandy Ground. The protected cove offers tranquil, crystalline waters and a long stretch of beach, where you can spend the day swimming, lounging in the sun and sipping the island’s famous rum punch. It won’t take much more than 20 minutes to get to the tiny island’s other main attractions, from the luxury resorts and golf courses to the Wallblake House, Anguilla’s only remaining plantation home.