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7 Must-See Stops On Your Day Trip From Rome to Tuscany

With rolling vineyards and beautiful ancient villages, Tuscany is one of the most romantic regions of Italy. And although it’s over 100 miles away from Rome, there are many charming destinations that you can easily reach in just a few hours. While some cities on this list can be reached by train, the best way to visit Tuscany is by car. Not only will this allow you to reach many off-the-beaten-path villages, but you’ll also get to see the spectacular Tuscan countryside as its meant to be seen!

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What is the Best Day Trip from Rome to Tuscany?

If you have a car, there are numerous towns and villages you can visit in Tuscany. Montepulciano, Cortona, and Siena are just a few picturesque places rich in history, culture, and cuisine. 

Without renting a car, you’ll be limited to bigger cities like Florence or Siena, as the smaller towns aren’t easily connected with public transportation. However, trains are generally faster and easier to navigate, so it’s an affordable option if you want to take a day trip from Rome to Tuscany.

But depending on what you’re interested in seeing and doing, there are many other fascinating sights in Tuscan worth visiting. And because most places are just 2 to 3 hours away, they can easily be seen on a day trip.

Florence

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As the capital of Tuscany, Florence is a must-see for anyone visiting Tuscany. This walkable city is packed with artistic treasures – from the iconic Cattedrale di Santa Maria del Fiore to the famous Uffizi Gallery. But with cobbled alleys and elegant 15th and 16th-century buildings, even strolling around the UNESCO-designed city center feels like you’re in an open-air museum.

As you make your way toward the Arno River, you’ll find the Ponte Vecchio, one of the most symbolic landmarks in Florence! This medieval bridge is lined with goldsmiths and jewelers (which are fun to look at but quite expensive in price). Instead, head to one of the leather markets around the city center to grab an authentic and fashionable souvenir. Getting to Florence is most manageable by train, as it’s only 1.5 hours instead of 3 hours by car.

Montepulciano

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When it comes to romantic Italian cities, few can compete with the medieval village of Montepulciano. Situated in the Chiana Valley 2 hours from Rome, Montepulciano is best known as a wine-producing region (so plan to sample a few glasses at one of the many enotecas!). 

Just peer over the valley, and you’ll find miles of rolling vineyards stretching as far as the eye can see.

However, it also has grand public squares, historic churches, and charming restaurants and cafes. 

It’s a pedestrian-friendly city, with most of its main attractions located in the historic center (although you should bring your walking shoes because it’s hilly up here!). Highlights include the Palazzo Comunale, the Santa Maria Assunta Cathedral, and the Museo Civico di Montepulciano.

Cortona

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This beautiful hillside village overlooking the Chiana Valley is a scenic destination for your Tuscan day trip (2.5 hours away). Dating back more than 1,600 years, Cortona is known for its Etruscan and Roman past just as much as its medieval history. 

You can visit the Cortona Archeological Park to see ancient buildings, ceremonial tombs, and ruins of city walls. Many artifacts can also be found in the Etruscan Academy Museum of Cortona (MAEC), which is located in the heart of the city.

Cortona is also a great place to same regional Tuscan cuisine. There are a seemingly endless number of restaurants and trattorias in the city serving traditional dishes. 

Don’t forget to try bistecca alla fiorentina (steak made with Chiania cattle) or tagliatelle with ceps (pasta with porcini mushrooms).

Pienza

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Pienza is a small town in southern Tuscany reachable 2.5 hours by car most famous for being the birthplace of Aeneas Silvius Piccolomini, or as he’s more commonly known, Pope Pius II. Although when he was born in 1405, the town was actually called Corsignano. 

After Piccolomini became pope, he rebuilt the village and named it Pienza – the city of Pius. As such, Pius is considered to be the “touchstone of Renaissance urbanism” as it was transformed into an innovative Renaissance city. 

As you walk through the UNESCO World Heritage designated city, you’ll encounter numerous palazzos, including Palazzo Piccolomini, Palazzo Vescovile, and Palazzo Comunale. The Cattedrale dell’Assunta is also a spectacular site, with a decorated altar painted by five artists from the Sienese School. 

Greve in Chianti

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Venture into the heart of the Chianti Classico region with a stopover at Greve in Chianti. Although it’s relatively small in size compared to other places on this list, it’s a worthwhile day trip with some fascinating buildings, monuments, and museums. 

Most of the bustle is centered around Piazza Matteotti, making it easy to explore the quaint artisan shops and cafes. 

However, Greve in Chianti is particularly famous due to its prime location near the Tuscan wineries. In addition to the vineyards, Chianti is also known for its prized extra virgin Tuscan olive oil and harvested black and white truffles. 

Although it’s 3 hours away by car, visiting Greve in Chianti isn’t an easy destination to reach, but it’s a must-do for any food and wine lover.

Siena

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No trip to Tuscany would be complete without visiting the vibrant city of Siena (located 2.5 hours from Rome).

With mouthwatering cuisine, picturesque city streets, and world-renowned museums, Siena makes for an action-packed day trip (I recommend staying a long weekend if you have the time). 

Start your visit at Piazza del Campo, an unusual shell-shaped square that hosts the biannual Palio di Siena horse race. Then visit the fresco-covered Cathedral of Santa Maria Assunta, the Palazzo Pubblico and attached Torre del Mangia, and the fortified Porta Pispini gate. 

And because Siena gave rise to the iconic Sienese school painters, you’ll find a number of excellent art museums too (although many paintings can be found inside the churches). 

Pitigliano

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The view of Pitigliano from afar is almost as impressive as the town itself. Built on top of steep cliffs made from volcanic rock, the entire town looks as if it was carved out of stone. 

nce you enter the gates, you’ll find century-old houses, fountain-filled squares, and winding passages that lead to different shops, restaurants, and markets.

Due to its large Jewish immigrant population who settled here in the 15th century, the town (located 2 hours from Rome) is affectionately referred to as Little Jerusalem. 

In addition to visiting the restored synagogue, I also strongly suggest trying Sfratti, a local Jewish pastry made of honey, orange peel, nuts, and white wine. It makes a great souvenir and an even better mid-day snack.

Although it’s just a few hours from Rome, Tuscany feels like an entirely different world. The lush landscape of olive groves and grape vines in the countryside is breathtakingly beautiful, while the historical villages dotted between them offer visitors the chance to experience authentic Tuscan culture and cuisine.

But be careful – a day trip to Tuscany can quickly become a week or even month-long journey, as there is always something enticing here to discover.