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.

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.

The approach to Menorca reveals white houses clinging to rocks with a historic town rising above one of the world's largest natural harbors, used as a port since the 3rd century BC. King Island floats halfway in, featuring ruins of a 6th-century basilica. The streets of Menorca present an interesting blend of ancient treasures, such as the medieval wall of San Roque Arch and the relics in the Museu de Menorca, and more recent gems, including the grand Georgian homes that remain from the British occupation of the island. The city's rich history is also reflected in its varied cuisine.

Once a sleepy fishing village, Marigot became St. Martin's capital during the reign of Louis XVI, who built Fort Louis to defend the colonial settlement's harbor warehouses. The formidable walls and cannons of the ruins overlook Marigot Bay and are well worth the short hike up. The town itself charms visitors with winding streets and colorful buildings. Restored St. Martinoise-style houses are now boutiques for luxury goods, all duty-free, while Marigot Market is a melting pot for local foods, spices, art and crafts.