An amazing Tuscany Road Trip to discover an unforgettable scenery!
A car is all you need! 🙂 Tuscany offers a rich territory not just in terms of traditions and culture, but also in terms of its varied geographical composition; hills, plains, mountain ranges, islands and seacoast. The beautiful lush landscape of Tuscany with its extensive green fields, hill towns and cypresses is probably the thing for which the region is best known.
Tuscany is in fact the ideal setting for scenic drives! Driving through Tuscany is a sight in itself, and is the perfect solution to really experience the atmosphere of this unique land.
The best thing is to avoid motorways, and enjoy the Tuscan scenery on winding roads in the countryside and panoramic routes far from the traffic; then driving becomes a truly rewarding experience.
Driving Tours of Tuscany: Tuscany Road Trip Itinerary
There are two main driving routes crossing Tuscany that we highly suggest you go through; both are famous for their sensational scenery and their beautiful sights, the Via Chiantigiana, and the Via Cassia.
Via Chiantigiana, the scenic drive through Chianti
The Via Chiantigiana, SR222 (see Map at the end of the page), that connects Florence to Siena through the stupendous countryside of the Chianti region, is one of the most beautiful routes of Italy.
Well known for its vineyards, cellars and extensive views over a pristine landscape, Chianti is the place where to get lost among centuries of history, hidden treasures and excellent food and wines.
Leaving Florence and heading south, you are soon surround by the typical Tuscan countryside and by small villages up the hills, like Strada in Chianti and Chiocchio.
Here are also intriguing medieval castles like the ones of Meleto and Verrazzano, also producing a fine Chianti Classico wine that you can taste, not too much though if you’re the driver 🙂
The castle of Montefioralle was home to the enigmatic Monna Lisa, portrayed by Leonardo da Vinci. This small charming hamlet is actually worth a visit for its atmosphere lost in time.
Continuing south we get to Greve in Chianti, heart of the Chianti Classico wine production, where to find lots of tempting food shops sheltered by lovely arcades, and a whole Museum devoted to wine.
Past Greve you find yourself in the nice hill town of Panzano in Chianti, the perfect place to enjoy some great local food, like the superb Florentine steak by the whimsical butcher Mario Cecchini.
After Panzano you go through woods inhabited by wild boars, hares and squirrels, until you get to the old military outpost of Castellina in Chianti, one of the nicest towns in the area.
Here was built the Consorzio del Chianti Classico, that in 1984, gets the DOCG brand for local wines.
Taking a little detour you might want to visit the villages of Radda and Gaiole where to find excellent restaurants, wineries for tastings, and workshops. Now make your way to the beautiful Castle of Brolio, where the recipe of the Chianti Classico wine was born, and where the ghost of the Baron Bettino Ricasoli is believed to wander at night, according to the legend.
Curvy roads then follow one after the other, until you get to the splendid Siena.
The Via Chiantigiana is an extraordinary road riding through times.
Via Cassia, ancient driving route running across centuries
The Via Cassia, SS2, (see Map below) is a very ancient Roman road connecting Florence and Siena to Rome through the Val d’Orcia. For most of its route the Via Cassia coincides with the historic Via Francigena, that the pilgrims were used to cross on their spiritual journey from Canterbury to Rome.
This secular route passes through the most spectacular countryside of Tuscany and probably of all of Italy; the type of landscape found in the most common postcards about Tuscany.
The Val d’Orcia is a unique combination of history, art, and scenic beauty, declared a Unesco World Heritage Site.
Start your itinerary driving south of Siena along the SR2 Via Cassia, so entering the Val d’Arbia and the fascinating Crete Senesi territory; wheat fields, undulating hills, isolated cypress trees and a mostly deserted landscape. We pass through the nice villages of Monteroni d’Arbia and Buonconvento. Buonconvento is a very nice medieval town encircled by walls, worth a visit.
Val d’Orcia Tour
Past Buonconvento, shortly after Torrenieri, the Via Cassia faces the inimitable landscape of the Val d’Orcia near San Quirico d’Orcia. Here begins the most spectacular stretch of this historic road.
East and west the Cassia, lie sensational villages and hamlets atop scenic hills.
San Quirico d’Orcia is one of the oldest villages in the area, and is perfect to take a pleasant walk, especially at the Horti Leonini, a wonderful example of Italian garden.
10 Km east of San Quirico is Pienza, the jewel of the Val d’Orcia, enchanting hill town with incredible 15th century architecture and a fabulous location. The views from the walls surrounding the village will leave you breathless.
Pienza is the perfect place to stop for lunch; wine and cheese specialties are not to be missed, while the many craft shops are all to discover.
15 kilometers west of San Quirico is the magnificent Montalcino, splendid medieval hill town with thick walls and an imposing fortress, famous for its Brunello red wine. Here are many wine bars and wine shops. The walkable walls of the castle will give you a breathtaking panorama on the countless vineyards surrounding Montalcino.
Returning on the Via Cassia, south of San Quirico, you find the lovely small town of Bagno Vignoni, with its magnificent square of water and its thermal baths. From the thermal waters of Bagno Vignoni we continue the road trip to the foot of the ancient volcano Monte Amiata up to Bagni di San Filippo, another thermal village where the water flows out from the earth at about 50 degrees.
During the ride is impossible not to notice a perfectly preserved fortress that dominates the entire Val d’Orcia, just 20 kilometers from Montalcino; the village of Rocca d’Orcia is a sight not to be missed. The Rocca a Tentennano dominates the entire valley with an unforgettable and never ending panorama.
We can then leave the Cassia for a while to get to the spectacular Fortress of Radicofani from which to enjoy another stunning vista all over the valley and all its beauty.
The drive then continue towards Rome…with many more sights to enjoy along the way.