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.

Montserrat represents a unique opportunity to experience the forces of nature that have forged the mountainous idylls of the Caribbean. The northern half has earned the title of the Emerald Isle of the Caribbean thanks in large part to its rugged and lush landscape with its forest-cloaked hills and valleys of ferns, but also to its rich Irish heritage that has been a significant part of the culture for centuries. On the coast, black and silver sand beaches strikingly contrast with the vibrant blues of the sea for a view that’s unique to the rest of the Caribbean.

Portugal’s capital on the Atlantic Ocean is comprised of several key districts built on seven hills. A good place to begin is the historic Alfama district, a maze of medieval streets and alleyways leading to a hilltop on which you will find the Castelo de São Jorge. One of Lisbon’s most popular attractions, the castle provides sweeping views over the city. Descend to the riverfront Baixa district to enjoy its shopping, restaurants and neoclassical architecture.

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.

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.

Las Palmas, the capital city of Gran Canaria island, is a bustling city that weaves the vibe of the Spanish mainland into a unique tapestry of life informed by world cultures including African, Chinese and Indian. A city of superlatives, it's one of Europe's biggest ports with one of the world's best climates and the cleanest air of any Spanish city according to a WHO study. Many also believe that the long, wide stretch of Las Canteras is one of the world's great urban beaches.