Chauffeur Service Rome – THE BEST Tuscany Day Trips from Rome (2025)
If you’re looking for the best Tuscany day trips from Rome, look no further! This comprehensive guide to visiting Tuscany when you’re in Rome shares everything you need to know when planning your trip.
Tuscany is honestly an ideal destination for a day trip from Rome. If you’re into history and culture, you can visit the UNESCO sites in Tuscany to see remarkably well-preserved medieval, Renaissance, and Etruscan architecture and relics.
Tuscany is also a foodie’s paradise. There’s fresh produce from local farms, and the area is also famous for its pecorino cheese production. And of course, you can also go wine tasting in Tuscany, sampling wines like Vino di Nobile and Brunello di Montepulciano.
With historic hilltop towns, world-class vineyards, rolling farmland, grand Italian landmarks and some of the most famous works of art ever produced, a trip to Tuscany is always worth it.
If you want to visit Tuscany from Rome, book your tour with Rome Air-Port Shuttle!
Chauffeur Service Rome – Top 10 Tuscany Day Trips from Rome
San Gimignano
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- Why visit: Known for its medieval architecture and UNESCO World Heritage status.
- What to do: Stroll through the historic center, visit the Torre Grossa and taste Vernaccia di San Gimignano wine.
- How to get there: 3.5 hours by car on our private tour.
The historic center of San Gimignano boasts UNESCO World Heritage status and is prized for its medieval architecture. It is a hill town surrounded by walls that date back to the 13th century. In the center is the triangular Piazza della Cisterna, with its well-preserved medieval buildings.
There used to be 72 towers in San Gimignano, but now their number has been reduced to 14. The Torre Grossa is the tallest in the so-called City of Beautiful Towers. San Gimignano also has the beautiful frescoed Duomo di San Gimignano church, which offers stunning views of Tuscany.
Siena
- Why visit: Known for its medieval architecture, UNESCO designation and rich history.
- What to do: Visit Piazza del Campo, climb the Torre del Mangia and explore Siena Cathedral.
- How to get there: 2 hours 50 minutes on our private tour
Like San Gimignano, Siena is known for its medieval architecture and is also listed by UNESCO. In this case, the central square is shaped like a fan, with 17 historic districts extending outwards. Piazza del Campo is home to the 14th-century Torre del Mangia and the Gothic Palazzo Pubblico, or town hall.
Cortona
- Why visit: Known for the Museums of the Diocesan and Etruscan Academy and a Renaissance cathedral.
- What to do: Stroll through the historic center, discover the Etruscan Museum and its archaeological park, and explore the diocesan art museum.
- How to get there: 2 hours 40 minutes on our private tour.
- Insider tip: Many consider Cortona to be the most livable walled city in Tuscany.
Cortona is known as the filming location for Under the Tuscan Sun, the 2003 comedy-drama starring Diane Lane. The city’s attractions showcase its rich Etruscan past and also include Roman roads, a Renaissance cathedral, and works of art in the Diocesan Museum.
Florence
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- Why visit: The iconic Italian city is considered the world capital of Renaissance architecture and art.
- What to do: Visit the Duomo, see Michaelangelo’s David statue at the Galleria dell’Accademia and discover artistic masterpieces at the Uffizi Gallery.
- How to get there: 3 hours and 20 minutes on our private tour.
The beautiful and world-famous Florence is not only the capital of Tuscany. It is also one of the world’s most important destinations for lovers of art, architecture and the Renaissance era. Famous museums such as the Uffizi Gallery and the Galleria dell’Accademia are just the beginning. Florence’s historic center is also a UNESCO World Heritage Site.
Montalcino
- Why visit: Known for its medieval architecture and the production of Brunello di Montalcino wine.
- What to do: Enjoy the breathtaking views, sample Brunello di Montalcino and visit the fairytale medieval castle.
- How to get there: 3 hours by car
- Insider tip: Montalcino red wine is made from 100% Sangiovese grapes.
If you like red wine, visiting this Tuscan hill town to sample the locally produced Brunello di Montalcino is an absolute must. The views from the top of the steep streets are also something to be savored, and to top it off, the medieval castle looks like something out of a fairy tale.
Montepulciano
- Why visit: Known for the Torre di Pulcinella clock tower and the panoramic views from the tower of the Palazzo Comunale.
- What to do: Climb the tower of the Palazzo Comunale; sample Montepulciano red wine; and explore the rambling streets.
- How to get there: 2 hours and 30 minutes by car
- Insider tip: Montepulciano red wine is made from 70% Sangiovese grapes, as well as Canaiolo, Colorino and Mammolo.
Not to be confused with Montalcino, Tuscany’s other “Monty,” Montepulciano is also known for its red wine production. In addition to its hilltop position and medieval architecture, the setting, set amidst the vineyards, is spectacular, and you can enjoy the views from the tower of the Palazzo Comunale.
Orvieto
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- Why visit: Known for its National Archaeological Museum, underground caves and white wine production.
- What to do: Discover the Museo Archeologico Nazionale, see the colourful cathedral, wander through the underground caves and visit St Patrick’s Well.
- How to get there: 1 hour 50 minutes by car
- Insider tip: Don’t miss the huge network of underground caves that will take you back to Etruscan times.
Like Cortona, Orvieto is rich in Etruscan history and therefore in traces of that era. It is also an important centre for wine production, including both dry and semi-sweet varieties. Lace, pottery and wrought iron are also produced in the area. It is one of the quickest Tuscan towns to reach from Rome, which also adds to its appeal.
Pienza
- Why visit: Known for its cathedral, the Palazzo Piccolomini and as the capital of pecorino cheese.
- What to do: Visit the Diocesan Museum, see the Piccolomini Palace and its rooftop garden, and sample the local cheese.
- How to get there: 2 hours and 50 minutes by car
- Insider tip: The cheese festival is held annually on the first Sunday in September.
Pope Pius II was born in Pienza and commissioned a Renaissance architect to create the ideal 15th-century city. The Tuscan settlement remains a prime example of Renaissance architecture and has been a UNESCO World Heritage Site since 1996. If you’re feeling romantic, seek out streets like Via del Bacio – the street of the kiss – and Via dell’Amore, also known as the street of love.
Pisa
- Why visit: Known for its leaning tower, baptistery and cemetery, all in Piazza dei Miracoli.
- What to do: Photograph and climb the iconic Leaning Tower of Pisa, explore Piazza dei Miracoli and stroll along the riverbank.
- How to get there: 4 hours by car; 2 hours 20 minutes by train; or private tour
Pisa is a pleasant, compact university town with the Arno River running through the center. The famous Leaning Tower is the main attraction, but Piazza dei Miracoli is also a good place for a picnic or just to stroll, and the square is a UNESCO World Heritage Site.
Val d’Orcia
- Why visit: Known for the scenic landscapes that characterize the Tuscan countryside.
- What to do: Drive the winding Montichiello Road, visit vineyards and explore hilltop towns.
- How to get there: Pienza – 2 hours 50 minutes by car
- Insider tip: Val d’Orcia is best visited on a road trip with an organized tour
The landscapes of Val d’Orcia have inspired artists of all genres and are filled with lush green hills, cypress trees, wheat fields, old farmhouses, vineyards and charming country roads. Take a road trip through this part of Italy and you’ll see the postcard Tuscan countryside. You can also visit towns like Montalcino and Pienza while visiting this area.
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