Let’s head to Tuscany

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The idea of a Tuscany road trip is existentially flawed, at least if you’re a wine drinker. I mean, how cruel is it to have an opportunity to taste some of the world’s finest wines alongside an obligation to get behind the wheel?

The good news is that I’ve crafted this post with safety—no drunk driving here, ma!—in mind. The better news? Even if you don’t drink alcohol, this road trip itinerary for Tuscany has something for everyone, not unlike my broader guide to spending 3 weeks in Italy.

Continue reading to learn why Italy’s fertile heartlands have become so world-famous, and how you can forge your own path along Tuscany’s extremely well-trodden roads.

The Logistics of Driving Through Tuscany

I was half-joking in the introduction—it’s relatively easy, in fact, to execute a Tuscany road trip without breaking the law. All wineries have spittoons, which allow you to imbibe without intoxication. The catch here, of course, is that you have to buy wine and take it back to your hotel. Personally, I don’t like drinking at “home,” so this is a difficult sell for me. (I’ll leave your group to fight amongst yourselves about who will be the designated driver!)

The most important thing to decide, before you travel, is where to pick your car up. Airports in Florence and Pisa (which has some overseas flights) tend to have the best selection of cars at the best prices. In terms of how to organize your trip, I’d recommend driving only in the rural parts of Tuscany, and maybe in Siena. Florence and Pisa are best explored on foot, and best traveled between via train.

Places to Visit in Tuscany

San Gimignano

A great reference point for your Tuscany road trip is the village of San Gimignano. A popular day-trip destination from Florence due to its easy bus connections, San Gimignano succeeds on two fronts. First, its walkable, medieval old town is just dripping with charm. Second, several wineries (including Palagetto, a personal favorite of mine) are within walking distance of it.


If you have just one day to ride the roads of Tuscany, Siena makes a great mid-point—which is to say, on an out-and-back journey from Florence and through San Gimignano and then back (from Siena) again. In addition to the many wineries that line the roads on the way to and from Siena, the city is charming and picturesque, albeit not enough that I usually recommend staying the night.


If you plan to extend your Tuscany road trip beyond Siena, meanwhile, Montepulciano makes for a good next step. Although slightly older and of a different architectural persuasion than San Gimignano, it boasts some of the same conveniences—namely, easy access from the old town center to many wineries, and endless views of beautiful wine country as well.


Is Pisa more than its most famous edifice? That’s difficult to say. On one hand, you’ll have plenty of time to decide—the Leaning Tower is about 20 minutes by foot north of Pisa Centrale station. On the other hand, while Pisa is a perfectly charming city, it has so much competition in Italy (and indeed, in Tuscany itself, as you’ll have seen over the last few paragraphs) that the tower will be the focal point of any time you spend here.


Even if you don’t end up hitting Tuscany’s dustier roads, you’re sure to spend a few days in Florence. One of Italy’s primary cradles of culture and history, Firenze (as it’s known in Italian) is home to many of the country’s most impressive museums, plazas, architecture and parks, all set amid the rolling hills that rise on either bank of the Arno River.

Other FAQ About Your Trip to Tuscany

What is there to do in Tuscany in 3 days?

If you have just three days in Tuscany, I’d recommend basing yourself in Florence. Spend one full day exploring that city, with an optional day trip to Pisa and its leaning tower sometime on day two. On day three travel into the Tuscan wine country, either via public transportation to San Gimignano, or by renting a car and exploring more freely.

What is there to do in Tuscany in 7 days?

Having a week in Tuscany opens up many more options. You can divide 3-4 days between Florence and Pisa, then pick up a car at one of their two airports. Hub yourself at the best Tuscan villa you can find, then spend days driving between wineries, towns and cities, including Montepulciano and Siena.

How can I spend 4 days in Tuscany?

If you have four days in Tuscany, overall, you can evenly divide it between Florence and the wine country: Two days, on foot, in Florence; and two days driving between villages and vineyards. If you have four days just in the rural part of Tuscany, the world is your oyster: You can either base yourself at a single villa and explore outward from there, or stay at two or more different Tuscan abodes and savor the variety.

The Bottom Line

Many travelers to Italy take a Tuscany road trip, but that doesn’t mean yours has to follow the same pattern. Whether in the rural reaches of the Tuscan wine country, in smaller towns and cities like San Gimignano and Siena, or in the large cities of Florence and Pisa, Tuscany offers a feeling you simply can’t find elsewhere in Italy. Rent a car for the entirely of your time here, or just for a day or two as you sleep in one of Tuscany’s famous villas. 

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