22 days in Italy & City of San Marino Itinerary

Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.

San Marino is a country characterized by its architecture--namely, the three towers that adorn the country's flag and coat of arms. As a result, most of the tourist attractions here center around the structures protruding from the hill of the country. The third-smallest nation in Europe, it is surprising that San Marino managed to gain independence from robust Italy. This status has created great pride among the Sanmarinese, although Italian culture is still quite influential as the country is completely surrounded by Italy. And while its size has obvious disadvantages, the advantages for tourism strongly outweigh them. Visitors don't need to travel to get a sense of the country (there isn't far to go!), and this generates an intimacy and friendliness among locals that is lost in most larger countries.

Forming the toe of Italy's "boot," Calabria is considered the Caribbean of Europe and may very well be the country's best-kept secret. Visitors can find everything from beaches to Byzantine churches here. Hillside towns, ancient Greek temples, and medieval castles and palaces are just some of the attractions scattered around one of the country's least-developed regions. Calabria remains largely unblemished by mass tourism, with many charming places to visit like olive plantations, orange groves, waterfalls, and lakes. Because it's bordered by the Mediterranean Sea on three sides, the water plays a huge role in the region's culture and cuisine. Calabria is also an up-and-coming producer of fine wines.