Welcome to the capital city of the British Virgin Islands… its Main Street lined with colonial-era buildings painted in shades of pastel with colorful shutters and delicate wood trim. Trek through the rain-forested Mount Sage National Park for sweeping views, or play on spectacular white sand beaches with names like Smuggler's Cove and Cane Garden Bay (immortalized in Jimmy Buffet's “Mañana”).

Island of celebrity hideaways and posh bungalows, considered by many to be the most elite and glamorous of all the Caribbean isles, St. Barts is home to 22 incredible beaches. Anse de Flamanes presents camera-ready scenery, Baie de St-Jean serves up beachside bistros, and Anse de Grand Cul-de-Sac offers an array of watersports.

Dominica is the nature lover's retreat from the rush of daily life, a fragrant tangle of rainforest that is easily explored from its capital, Roseau. The tiny volcanic island offers both golden- and black-sand beaches to loll on – Batibou is a dazzler – but it's the wild beauty of its interior that enchants. Hike through the Titou Gorge, familiar from the moviePirates of the Caribbean: Dead Man's Chest, dipping into the chasm's cool waters to swim to the waterfall at its end. Climb into the mountains at Morne Diablotins National Park (one of three on the island) for the chance to catch sight of the sisserou parrot. And delve into history at Fort Shirley, scene of an important slave revolt. Snorkeling in the bubbly, volcanic waters at Champagne Reef, shopping for handcrafted gifts at the Old Market, and watching out for sperm whales – this is the only country whose waters they live in year-round.

Basseterre is the compact coastal capital of the Caribbean island St. Kitts, where verdant hills and sugar-white sands meet architectural artefacts of French and British colonial rule. The town center is anchored by Independence Square – formerly Pall Mall Square – an 18th-century plaza with an ornate fountain and lush lawn, while nearby, the Georgian-inspired Circus is modeled after London's own Piccadilly. Venture just beyond the city to explore the UNESCO-listed Brimstone Hill Fortress National Park, an 18th-century British-built fortress that offers sweeping views and serves as a striking reminder of the island’s layered history.