We meet in Cortona (1 night) for a walk that includes a stroll past the home that inspired Under the Tuscan Sun. A countryside olive-oil tasting punctuates out first day. In the morning, we explore medieval Siena before settling into our palazzo hotel in Spello (2 nights) and a wine-tasting in our friend's cellar.

Assisi is nearby and we'll make the pilgrimage to experience its glorious art and the landmarks of St. Francis' life. Our walks include a grand picnic and a visit to Deruta's ceramic workshops. En route to Orvieto (3 nights), we'll pause for a cheese-tasting. Next day, we join the locals for a stroll along Lake Bolsena. Our views overlook sunflower fields and vineyards that produce the region’s famed wine. On our last country day, an art historian leads us to the enigmatic Etruscan tombs in the surrounding hills.

Finally: Rome! We've arranged for a friend to give you his own unforgettable perspective on his beloved town. It's a memorable morning…and a great orientation if you decide to treat yourself to some time in the Eternal City.