Surrounded by rugged terrain and lush vegetation, La Romana is home to crystalline waters, white sand beaches and impressive coral reef life. It's a gateway to charming villages such as Bayahibe, ecological trails and numerous golf resorts. In the town center is El Obelisco, painted with images of local Dominican life. Nearby Altos de Chavon is a replica 16th-century village and cultural center featuring artist studios, galleries, an archaeological museum and sweeping views of the Chavon River.

The yachting capital of Martinique, Le Marin sits at the head of a deep bay and has one of the largest marinas in the Caribbean. At the center of town is one of the area’s few historic sights, the 18th-century stone church of Église Saint-Étienne, whose design suggests an overturned ship’s hull. Businesses in Le Marin are oriented to sailors and yachtsmen, who enjoy the lively ambience in the waterfront bars and clubs. The nearby peninsula of Sainte-Anne is home to the island’s best beaches, the celebrated Grande Anse des Salines among them.

With seas as clear as those in the Bahamas and landscapes worthy of a film set, the gorgeous Aeolian Islands were obviously favored by the gods. There are eight islands in all with a variety of volcanic landscapes and local color, and each with its own unique character. Lipari is the largest with a lively Old Town of narrow streets clustered beneath an ancient citadel.

Montserrat represents a unique opportunity to experience the forces of nature – both destructive and creative – that have forged the mountainous idylls of the Caribbean. After decades of dormancy, the island’s Soufrière Hills volcano erupted in 1995, causing widespread devastation. Ongoing explosions and other volcanic activity turned more than half the land into an “Exclusion Zone.” Incredibly, the northern half was largely untouched, its rugged landscape still as lush and green as the historic nickname of “the Emerald Isle” – also a nod to the many Irish who settled here – would suggest.

Medieval hilltop towns spread out across the undulating countryside where tall, slender cypresses march like sentinels past rolling vineyards. Iconic names like Chianti, Brunello and Vino Nobile are celebrated the world over, but the art and architecture of Tuscany may be the region’s biggest draw. Just a few hours from Livorno, you can visit Florence: the cradle of the Renaissance, beloved by great thinkers like Dante and Galileo, and utterly captivating.