Collected by Rob Tesoriero
Via Enzo Mangiavacchi, 37, 53026 Pienza SI, Italy
One of the most delicious towns in Tuscany - and most beautiful - is the charming Pienza. Situated between Montepulciano and Montalcino in the scenic Val d'Orcia, centuries-old Pienza is best known for its rich pecorino cheeses. Many feel that the...
Via Gino Severini, 3, 53026 Pienza SI, Italy
One of the most charming towns we visited during our May trip to Italy was Pienza, situated in Tuscany between Montepulciano and Montalcino (also worth a visit if you're in the area). Pienza is best known for its delicious pecorino cheeses,...
53037 San Gimignano, Province of Siena, Italy
One of the best things about the beautiful Tuscan hilltop town of San Gimignano - and there are many - is the wonderful street art offered for sale throughout the town. You can watch the artists at work, making the experience even more special....
52044 Cortona, Province of Arezzo, Italy
While in Italy in May, my husband and I especially enjoyed our drives through Tuscany and Umbria. The hill towns throughout the region are wonderful to explore, and the views along the winding cypress-lined roads are picture perfect, like these...
Corso il Rossellino, 16, 53026 Pienza SI, Italy
The town of Pienza in beautiful Tuscany is a must-see on any trip to the region. The drive to Pienza winds you through the famed Val d'Orcia, whose postcard-perfect views most people associate with Tuscany: rolling green hills, stately cypresses,...
52031 Anghiari AR, Italy
If you find yourself with a car in eastern Tuscany, the town of Anghiari is worth a visit. Located between the Arno and the Tiber Rivers, Anghiari is a bustling medieval town with a panoramic view of the green valley below. Anghiari's thirteenth...
Greve in Chianti, Metropolitan City of Florence, Italy
If you find yourself on a road trip from Florence into the Tuscan countryside, take the Chianti road and stop for lunch or a stroll in Greve in Chianti. The town square often hosts a market—we were there on the flower market day—and houses a Museo...
53045 Montepulciano, Province of Siena, Italy
Montepulciano is a charming hill town in Tuscany. Walk the streets to get a feel for its appeal. On the outskirts of town visit San Biagio, a 16th-century church. This late-Renaissance building was constructed on the site of a pre-existing...
Piazza di S. Francesco, 5, 53045 Montepulciano SI, Italy
Sunsets on Val D'Orcia are one of the most incredible views for those who are looking for an unforgettable Tuscan experience. From Piazza San Francesco in Montepulciano, you can admire an infinity of colors, changing every season. This hotel...
Via Ombrone, 1, 05018 Orvieto TR, Italy
Where's the beef? Who cares - when you come to Orvieto the thing to eat is "porchetta" and they do it in so many different ways that you'll just have to try them all. Either hit a restaurant or just go to one of the butcher shops and try a bit of...
Piazza Garibaldi, 1, 52044 Cortona AR, Italy
If you've just arrived in Cortona, Italy (the Tuscan hill-town made famous in Frances Mayes' memoir, Under the Tuscan Sun), I recommend dining on your first night at Ristorante Tonino. Your seat on the outdoor terrace guarantees a spectacular...
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