Perhaps best known these days as the setting for the book and movie “Under the Tuscan Sun,” gorgeous hillside Cortona has a long history dating back even before its time as an important Etruscan center. Top attractions include the Duomo (Cathedral), the small Museo Diocesano across the piazza with its superb art collection, and the fascinating Museo dell'Accademia Etrusca with its assembly of Etruscan and Roman era items. Cortona is also bursting with splendid churches spanning many periods.

An ancient town of just under 3,000 between Florence and Siena, picture-perfect Castellina In Chianti is set in the wine-famous Chianti Hills. The many wonderful sights include the imposing 14th-century Rocca (Fortress), offering spectacular views of the town and surrounding countryside, the 16th-century San Salvatore church and the Via delle Volte medieval arched passageway. Just outside of town are the pre-Roman Etruscan burial tombs of Monte Calvario and the Necropolis of Poggino.

In St. John's, the capital city of Antigua, farmers markets, candy- colored architecture and the ruins of sugar plantations vie for attention with a kaleidoscope of coral reefs and sailing adventures. Salute the white baroque towers of St. John's Cathedral that dominate the skyline before joining the flocks of cruise passengers on a Heritage Quay shopping excursion. To experience the island's early cultures, visit the Museum of Antigua and Barbuda, housed in a 1750s colonial courthouse.

Ecotourism is alive and kicking on St. John. There's more than enough to do on land, from watching for wildlife in the national park to hiking miles of trails or strolling sandy white beaches. Hit the water for amazing snorkeling, swimming, even underwater photography—of course. This is the Caribbean, after all.