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Tuscany Road Trip

A quintessential Italian road trip takes you to delightful Tuscan and Umbrian medieval hilltop towns and some of the most famous places in the country.  Each driving leg is short, which gives you plenty of time to explore your destinations.  However, part of the charm of this road trip is enjoying the countryside and hill towns, so feel free to get off the main roads and get (temporarily) lost driving around some of the smaller roads and exploring the areas you pass through. See the itinerary of this Tuscany road trip all the way to Umbria.

Tuscany road trip – From Tuscany to Umbria

A Tuscany road trip is great if you’re looking for the best places to visit in October. The road trip starts in Florence.  Spend at least three days in Florence before starting the trip. Highlights in Florence include admiring the art in the Uffizi Gallery and seeing Michelangelo’s statue of David at the Galleria dell’Accademia; watching the people (and statues) in the 14th Century Piazza della Signoria, walking over the Ponte Vecchio bridge; wandering through the Duomo (cathedral), and soaking in the views of the city from the Piazzale Michelangelo in the early evening. Florence may be crowded, but it is famous for a reason – it truly is a magical place. Tuscany is like magic, and it’s really worth stopping by for a few days in one of the villas in Tuscany and enjoy this magic. We’ve got a list of the 15 best villas in Tuscany, check them out!

Stop 1: Siena

Piazza del Campo with Palazzo Pubblico, Siena, Italy

There are so many things to do in Tuscany. From Florence, it is a one-hour direct trip to Siena.  Although you could visit Siena as a day trip from Florence, it is much better to make this a standalone stop on your road trip, as Siena is especially charming after the Florence day-trippers have left for the day. 

Spend a day or two in Siena. The crown jewel of the town is the beautiful shell-shaped main square, the Piazza del Campo, considered to be one of the greatest medieval squares in all of Europe.  There are cafes around the edges of the plaza, and this is the perfect place to sit and enjoy a coffee (or glass of wine) and soak up the incredible beauty of this place.  If you time your visit just right, you can even see a horse race around the plaza twice a year. 

No matter when you go, don’t miss the striped duomo/ cathedral, one of the most beautiful in the country. The white and green/ black marble stripes are especially striking.  Inside, you can climb to the top and look down at the incredible mosaic floor.  Like elsewhere in Italy, it can get crowded, so take advantage of the fact that you are staying in Siena overnight and go early or late in the afternoon to avoid the crowds. If you’re planning to visit Tuscany in winter, Siena is still a lovely option! Check where to stay in Siena!

Stop 2: Perugia

Perugia, Italy

From Siena, it is a one hour and 15-minute drive to Perugia, where you can easily spend another couple of days.  Set atop a hill, the historic city center of Perugia has beautiful views over the surrounding countryside. 

In the main plaza in Perugia, the Piazza IV Noviembre, don’t miss the incredible medieval marble fountain covered in carvings of biblical scenes and zodiac signs, the Fontana Maggiore.  Also be sure to visit the nearby National Gallery. From the Piazza IV Noviembre, a long, flat, wide pedestrian street stretches to the Piazza della Repubblica.  This is one of the best – and most popular – places in all of Italy for the passeggiate – the early evening stroll through the streets (to see and be seen) that is an integral part of Italian culture.


There is an aqueduct right through town that you can walk along the top of, the Via dell’Acquedotto.  Also don’t miss the imposing Etruscan gate, the Arco d’Augusto; an Etruscan well; and an ancient water cistern that is well-hidden deep beneath the streets. 

Perugia is also home to the delicious Perugina chocolates.  Their most famous product is Baci, which means “kisses” in Italian, and a tour of their factory includes free tastings of these and other mouth-watering goodies! 

Tuscany road trip – All the way to Umbria region

Stop 3: Assisi

basilica st francis assisi
Assisi, Italy

The next stop on your road trip through Tuscany and Umbria is Assisi.  It’s just 30 minutes from Perugia but is also worth staying in overnight since it is especially delightful after the day-trippers and coach crowds have emptied out the narrow streets. Wrapped like a ribbon around the side of a hill, Assisi is a great place to wander.  Start at the top and make your way down to the stunning Basilica Papale e Sacro Convento di San Francesco d’Assisi, home of the Franciscan order.

The last day of your road trip ends in Spoleto but has several stops along the way. Just 15 minutes from Assisi is another delightful hill town, Spello.  Park at the bottom of the hill and climb the narrow, cobbled streets to the top. Visit the Villa dei Mosaici di Spello to see incredible ancient mosaics, and wander through the beautiful gardens at the nearby Villa Fidelia.

Most of the medieval towns in the area sit atop hills, but not Bevagna.  This is a rarer valley village and is also fun to explore.  The center of the village is the Piazza Silvestri.  This is a great place to wander and soak up the flavor and culture of Umbria.  You can also pick up Deruta pottery here at great prices.

Stop 4: Spoleto

Spoleto – photo from Italy Magazine

Another 15 minutes away is the bucolic Montefalco wine region.  Driving along narrow roads through hills covered in vineyards is amazing.  Stop at one of the wineries (Azienda Agraria Scacciadiavoli is recommended) for a tasting.  Both reds and whites are grown and produced here, so you are sure to find something you like.

A 30-minute drive takes you to your final destination, Spoleto.  This is another beautiful medieval town with narrow, cobbled streets to explore, centered around the lovely Piazza del Duomo and the small duomo/ cathedral itself.  An aqueduct (Ponte delle Torri) on the edge of town is especially well-preserved and famous. Try to get a room overlooking the surrounding hillsides, which are covered in picturesque vineyards and olive groves. The 15th-century guest house, Palazzo Sant’Angelo, is recommended.

This is the end of your road trip through the hills of Tuscany and Umbria. Total distance is 285 km.

James Ian from Travel Collecting

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