Postcards from Italy

Three Top Tuscan Road Trips

With its milder temperatures, gorgeous golden light, and richly colored countryside, fall is an ideal season to head for the open road and explore Tuscany by car. Though Florence is easy to navigate on foot, you’ll need wheels (either your own in the form of a rental car or a private car service with driver) to reach many of the smaller towns in the Tuscan countryside—especially if you plan on visiting more than one hilltop village and savoring picturesque rural landscapes along the way.

Here are three of the most scenic road trips in Tuscany to consider, all of which combine iconic views, treasures of art and architecture, and top-shelf food and wine. Choose between the wooded mountains of the Casentino forest, the coastal countryside of Lunigiana, or the UNESCO-listed hills of the Val d’Orcia. 

A Spiritual Journey through the Casentino Valley

Photo by Christopher John SSF via Flickr licensed under CC BY 2.0

This secluded valley flies under the radar of most international tourists, but the Casentino is one of the most scenic stretches of countryside in Tuscany, covering the area between the cities of Florence and Arezzo. The Apennines line one side of this forested valley and the impressive Pratomagno peaks line the other, making it a favorite day-trip destination for Florentines looking to escape the city’s oppressive heat in the summer. Much of this area is part of the Casentino Forest National Park, one of the largest and most pristine natural areas in Italy, covering almost 150 square miles.  

There are a number of storied religious complexes that are tucked in these thick woods, including the Abbey of Vallombrosa, founded in 1038 and mentioned in John Milton’s Paradise Lost. Located just an hour from Florence, this peaceful spot seems worlds away from the bustling city. The Sanctuary of La Verna, where Saint Francis is said to have received the stigmata, is also located in this area. This vast complex is a popular pilgrimage destination and comprises a monastery, church, museum, chapels, and the grotto St. Francis used as his monastic cell.

While driving through the Casentino valley, be sure to stop in Poppi, considered one of the most picturesque hamlets in Tuscany and home to the beautiful 13th-century Castello dei Conti Guidi and its Biblioteca Storica Rilli, a historic library holding hundreds of medieval manuscripts and historic documents.

A good lunch choice is La Tana degli Orsi (Viale Roma, 1; +39 0575 583377) in the town of Pratovecchio, well-known among Tuscan foodies for its local Casentino cuisine and extensive wine list.

Lunigiana, An Unknown Corner of Tuscany 


If you have never heard of Lunigiana, you’re not alone. This quiet corner of Tuscany is far from more famous A-list areas like Chianti and its distance from the tourist track has helped it retain its authentic atmosphere. Set near the border with Liguria and known as “the land of the 100 castles”, Lunigiana has a wealth of postcard-perfect medieval villages and towns, including Filattiera, Bagnone, Pontremoli, Villafranca and the 12th-century Malaspina castle, and Fivizzano. This area is also home to the underrated town of Carrara, known for the historic marble quarries in the nearby Apuan Alps and local “lardo di colonnata“. 

Just south of the Lunigiana is an equally picturesque area known as Garfagnana, tucked between the ridges of the Apuan Alps and the Apennines and known for its hearty cuisine. The top towns here are Lucca, Castelnuovo di Garfagnana, and Barga in the Serchio River valley. The latter is known as the most Scottish town in Italy due to a large number of residents having emigrated to Scotland in the early part of the 20th century and the local cuisine features a variety of dishes featuring mushrooms and chestnuts foraged from the nearby mountain slopes. A great place to sample local fare in Barga is Da Arista (Piazza Salvi, 6; +39 0583 723062), a casual café beloved for its lively host, Giovanni.

The Rolling Hills of the Val d’Orcia


The otherworldly beauty of the Val d’Orcia has inspired artists and poets for centuries. Covering the hilly countryside from Siena to Monte Amiata, this stretch of Tuscany is known for its cypress-lined hills and lanes that make for some of the most iconic landscapes in all of Italy.

Drives through this area will take you past oak forests, olive groves, and vineyards that produce Brunello and other premier wines, as well as a number of quintessential hilltop villages, including Pienza, known for its Renaissance architecture and aged pecorino sheep cheese. Other worthy stops including San Quirico and Montalcino; gourmands may also want to visit San Giovanni d’Asso’s Truffle Museum.

Monte Amiata was once a rumbling volcano, and the area’s geothermal activity continues in the thermal baths of Bagno Vignoni and Bagni San Filippo, perfect for a quick soak to break up your drive. Another highlight is the 15th-century estate of La Foce, one of the most beautiful gardens in Italy. The adjacent Dopolavoro restaurant (SP40, 90; +39 0578 754025) is an ideal choice for sampling classic dishes from the Val d’Orcia. 

Related posts:

Driving in Italy: When You Must and When You Shouldn’t

Want To Rent A Car In Italy: A Few Things To Consider

Tuscan Villages to Discover: Montepulciano, Pienza, and Montalcino

Travel Specialists

Maria Landers

Brian Dore