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Tuscany Road Trip Itinerary | Florence to Siena By Rental Car

Tuscany Road Trip Itinerary

There’s no better way to experience the true sights and smells of Italy than by taking to the road and exploring at your leisure. Start your vacation in the romantic city of Florence and from there put together your own personalized Tuscany road trip itinerary.

One of the best places to visit from Florence is the historic town of Siena, which is just an hour away by car. What’s more, by taking a trip from Florence to Siena by car you also get to travel at your own pace, make some stops whenever you want, and enjoy many exciting locations along the way:


Florence, Italy

Known for its subtle beauty, impressive art, and for fostering some of the greatest minds throughout history, Florence is one of Italy’s “must-see” cities. The city gave birth to the Renaissance movement and was instrumental in the birth of Renaissance Humanism, a social ideology that encouraged the citizenry to participate in civic duties, and paved the way for many of the modern philosophical theories we engage today.  Much of the city’s ancient architecture is still intact, and much is almost unchanged after 700 years. Be sure to visit the famous Piazza della Signoria, which is home to the Uffizi, the world’s finest collection of Renaissance art.

Strada in Chianti

Strada in Chianti

Take the scenic Tuscan highway, the Via Chiantigiana through the famous Chianti region on your journey from Florence to Siena and start by stopping off at some of the region’s beautiful vineyards and olive groves. You can also stop off at one of the many small towns in this area, such as Strada in Chianti. This pretty medieval town features a number of historic churches and some great vineyards to explore and sample!

Panzano in Chianti

Panzano in Chianti

The hilltop village of Panzano in Chianti is another picture perfect stop off on your drive. Exactly halfway between Florence and Siena, the town is a charming destination with some incredible restaurants – it’s the perfect stop for lunch! Walk through the town’s main piazza and explore the historic churches. From here you can also drive just a few minutes to the walled medieval village of Montefioralle – famous for the Castle of Montefioralle, which was once home to the enigmatic Mona Lisa, the muse for Leonardo da Vinci’s great work, The Mona Lisa.

Radda in Chianti

Radda in Chianti

You will be struck at first by the imposing medieval walls that surround the small town of Radda in Chianti, a town that is tucked between the valleys of Arbia and Pesa. Dating back to the 9th century, Radda in Chianti is an immaculate example of an old medieval city, with narrow streets and towering buildings at every turn. At one point in its history, Radda in Chianti was in fact the capital of Chianti, today, however, it has more of a small-town feel to it, with local festivals and Italian flavors on offer for most of the year. The town also has some of the best Chianti wines, so be sure to order exclusively local.


Siena, Italy

Known as Italy’s “open-air museum,” Siena has more impressive architectural masterpieces than many of Italy’s cities, but it isn’t over-the-top about it. Siena is a city that is all about discovery, from its hidden medieval monuments on every corner to tucked-away restaurants that feel more local than cosmopolitan. However, with its excellent food, distinctive buildings, and plenty to see and do, there’s no mistaking that you are in a city. Walk through the famous Palazzo Pubblico and visit the Duomo of Siena to remind yourself of this city’s incredible history, before strolling through the local neighborhoods of the city to open up the heart and soul of this wonderful place.

Kemwel will Make your Tuscany Road Trip Smooth and Affordable!

Taking in Florence to Siena by car rental is the ultimate Tuscan getaway. Make sure you’re getting the best deal possible with a cheap car rental in Tuscany from Kemwel! Kemwel offers affordable car rentals in Italy and worldwide. While planning your next Tuscany road trip, remember that Kemwel offers some of the best travel deals on everything from cheap car rentals to cozy hotels and more. Simply browse our rates online or give our friendly travel experts a call, toll-free at 1-877-820-0668.


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