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Stayed in the smallest village, Riomaggiore. It has one main street and one bar, but you can easily reach the other four cities by train (or foot!) Instead of renting a hotel/hostel, about fifteen of us were able to cram into two small apartments. This also gave us the opportunity to cook a typical Italian dinner. The five village hike is, of course, a must do, but be sure to go find a bed of rocks overlooking the Ligurian sea and give yourself time to simply BE.

Visited Cortona right after they lit Christmas lights throughout the town. It was a foggy, but beautiful day. Try to explore every little nook and cranny. Wandering the random narrow streets, you’ll discover amazing views and a charming picture of Italian life. An interesting little adventure: walk the 30 minutes down the hill to the train station. We traveled on a holiday and had to resort to this slightly dangerous, but memorable little jaunt.

A few great things to do here: rent bikes and ride along the city walls, find the Gelateria owned by a friendly British couple, visit the small shops and practice your Italian. The people here are extremely friendly. Perhaps not as fed up with American tourists?

I lived in Siena, Italy for about four months during the Fall/Winter of 2005. Amazing! I recommend this small city to anybody traveling through Tuscany. It’s a must see!