At just 238 square miles (roughly the size of Chicago), the island of St. Lucia is the ultimate quaint Caribbean escape. An ocean-view cottage at Sugar Beach, A Viceroy Resort is a nice way to unwind, and you can take your relaxation a step further with a massage in a tree house on the resort property. Once recharged, check out one of Sugar Beach’s kayaks or some snorkeling gear and explore the coastline. You can also take the two-hour hike to Gros Piton for a bird’s-eye view of your little slice of paradise. And while it might be tempting to spend your whole trip on the property (everything you need is within arm’s reach, after all), a meal of curried crab at the Old Plantation Yard will make you feel like a local.
—Elizabeth Doyle