It’s a once-in-a-lifetime must-see, and you once you’re here, you’ll never want to leave again: rich in history, culture and cuisine, Tuscany has so many diverse experiences to offer. You don’t want to miss out on any of them; so let us guide you through your Tuscany road trip. Land in Florence, rent a ride, check in hotels along the way and just enjoy la dolce vita.
Tuscany is crossed by roads (‘Via’) built during the Roman times and connecting the most important areas. This road trip will go through parts of Via Francigena, an ancient road and pilgrim route starting in Canterbury and ending in Rome. You’ll probably notice various signposts along the way.
We’ve also set up a playlist of Tuscany tunes to keep you and your passengers happy during the road trip!
The journey starts in Florence, center of the Italian Renaissance and home to some of the best cuisine in the country. Set at least two days aside here.
Florence is Tuscany’s beating heart: don’t miss the Cathedral Santa Maria del Fiore and its innovative dome designed by Brunelleschi to withstand lightning, earthquakes and the passage of time. Only a few steps away, you’ll find one of Italy’s most beautiful bell tower, Giotto’s Campanile. It belongs to the same complex of buildings, so you’ll get a package of marvelous sights all-in-one.
Just a five-minute walk and you’ve reached the famous Piazza della Signoria, the L-shaped square hosting Palazzo Vecchio, Florence’s city hall dating back to the 14th century, and is surrounded by a wealth of magnificent buildings, like the Loggia della Signoria, Tribunale della Mercanzia, and the Uffizi Gallery – the latter exhibiting masterpieces from the Italian Renaissance (Botticelli, Michelangelo, Caravaggio, just to name a few).
At this point, head towards Ponte Vecchio for a romantic walk, if you can find your way among the crowds of tourists.
Fiorentina steak? A Lampredotto sandwich? Or maybe in the mood for a Ribollita soup? Make sure to taste as much as you can, but take note: Enoteca Pinchiorri is the place to go if you want to play it safe! The chef, Annie Féolde, is the first woman to be awarded three Michelin stars in the Italian restaurant scene. Located in a 16th century palace, this restaurant houses an expansive wine cellar of over 70,000 bottles!
On a budget? There are plenty cheaper options that will still give you the opportunity to taste high-quality local food. After all, Lampredotto is typically a street food. Aurelio in Bernardo Tanucci Square is considered the ‘King of Lampredotto’. No matter where you choose to eat, always accompany the food with a glass of Chianti wine.
Recommended Florence hotel: La Scaletta Hotel Florence (rates start at €120 [$134] per night)
Certaldo (37 miles)
Drive through the colorful roads to Certaldo, located 37 miles south from Florence. Part of Elsa Valley, known for its production of crystal glassware, Certaldo has its roots in the Roman-Etruscan age. Certaldo is characterised by narrow streets, little squares and a typical medieval structure perfectly preserved. With an exception: Palazzo Pretorio was rebuilt in the 15th century and today houses contemporary art exhibitions.
Certaldo, contrary to most cities, doesn’t have a proper main square. Instead, the long wide street Via Boccaccio, that takes its name from the famous writer who lived here, was the place where most of the official ceremonies were held.
Certaldo’s official symbol is the onion. So, don’t be surprised if it’s present in all dishes – even desserts!
Recommended Certaldo hotel: Il Paluffo Bed and Breakfast (rates start at €157 [$175] per night)
San Gimignano (8 miles)
A short 30-minute car ride south of Certaldo and you’ll find yourself in the immense historical site of San Gimignano.
In the 14th century, every wealthy family in the area built a tower in order to show its economical power. There were 72 in total and they all had different functions depending on the floor: workshops at ground level, bedrooms on the first floor and the kitchens on the top floor. With time the towers were extended to accommodate larger inside spaces and wider openings and turned into palazzis, AKA splendid residences.
Though only 13 towers still stand, you can admire the unique architecture mixing different styles and influences from neighboring towns. Visit the Duomo (the Cathedral) and discover its beautiful frescoes, then go to Piazza delle Erbe, and don’t stop exploring around: you are in a UNESCO World Heritage Site after all!
In the city center, the restaurant Perucà prepares a dish you’ll surely want to try: ‘Fagottini del contadino’ – ravioli filled with pecorino cheese and pears served with saffron sauce, pine nuts and more pecorino cheese. Don’t forget to sample the local white wine, Vernaccia di San Gimignano.
Recommended San Gimignano hotel: Hotel L’Antico Pozzo (rates start at €92 [$102] per night)
Volterra (18.6 miles)
After a good night’s sleep, head off once again for the next stop on your Tuscany road trip. Drive 45 minutes south-east of San Gimignano and you’ll reach the town of Volterra.
Volterra belongs to the province of Pisa, and has been the setting of various cultural and historical developments since the Roman-Etruscan age. The city has an untouched medieval look and is enclosed in the ancient city walls, perhaps built around the 4th century. Since then not much has changed and it’s therefore an authentic experience of the past.
In Piazza San Giovanni you’ll find several buildings: the Cathedral, the Baptistery, the Opera house and the Santa Maria hospital. But you should save some time to see the Medicean Fortress and the great Roman Theater.
Follow your heart! There is much more than one traditional dish: Zuppa di Volterra, hare or boar pappardelle, a great variety of cheeses and seasonal truffles.
Recommended Volterra hotel: Hotel Residence Villa Rioddi Volterra (rates start at €99 [$198] per night)
Monteriggioni (24.8 miles)
Want to explore more from the Middle Ages? Head to the walled town of Monteriggioni, located 25 miles east of Volterra.
Monteriggioni is part of the area Val D’Orcia, dominated by the sight of the majestic Castle of Monteriggioni and the fortified wall with 14 towers used for defense. The wall harmoniously follows the curves of the hill as they rise and fall. Due to its intact condition and picturesque setting, Monteriggioni has been the set of different movies, such as The Gladiator and The English Patient.
L’Antico Travaglio, in the main square, prepares tasty pappardelle with chianina ragù (meat sauce prepared with minced meat from the Chianina cattle breed). Enjoy it along with a glass of red Cigolino del Castello di Monteriggioni.
Recommended Monteriggioni hotel: Antico Borgo Poggiarello (rates start at €115 [$128] per night)
Siena (15.5 miles)
One of the most visited destinations in Tuscany, Siena is home to the incredible Cathedral Santa Maria Assunta, decorated with white and greenish-black marble in alternating stripes, and displaying frescos by Renaissance artists Donatello, Michelangelo, Ghirlandaio and Pinturicchio. Visit the Baptistery, built as an extension to the Cathedral: here you will find hexagonal baptismal font, featuring sculptures by Donatello and Jacopo della Quercia.
The main square, Piazza del Campo, is where the infamous Palio di Siena takes place. Since 1644, a horse race is held biannually (on July 2nd and August 16th) to nominate the winner among 10 competitors – namely 10 out of the 17 city districts. Each rider is dressed in a colorful garb that represents the banners of his district. The entire city comes together for a day of celebration and cheering.
End the day with great views of the city from the Mangia Tower.
For a filling meal, go for the Fiorentina steak at Osteria Da Divo just a stone’s throw away from Piazza del Campo. For a lighter dish, choose an aperitivo at Toscana Golosa located in city center, but away from the crowds. Pair your meal with Bianco Vergine della Valdichiana.
Recommended Siena hotel: Palazzo di Valli (rates start at €84 [$93] per night)
Montalcino (26 miles)
Take the one-hour drive south from Siena to the medieval village of Montalcino. But make sure to book a hotel beforehand here, because you’ll simply have to taste the local wine Brunello di Montalcino.
The Brunello has garnered a lot of praise throughout its history that goes all the way back to the 14th century. Yet it wasn’t until the mid-19th century, when a local farmer isolated certain plantings of the Sangiovese vines in order to produce a wine that could be aged for a long period of time, that this wine reached its current quality peak. In 1888, the farmer’s son released the first batch of the ‘modern’ Brunello di Montalcino that at that point had been aging for 10 years. Less than a century later, the Brunello had built a reputation as one the best and rarest Italian wines around.
If you happen to be planning your Tuscany road trip in July, make sure to be in Montalcino during the annual Jazz & Wine Festival (usually held mid-July).
Mix the wonderful red wine with a hearty meal at Osteria di Porta al Cassero.
Recommended Montalcino hotel: Si Montalcino Hotel & Restaurant (rates start at €110 [$123] per night)
Abbazia di Sant’Antimo (6 miles)
Abbazia di Sant’Antimo, located a mere 15-minute drive from Montalcino, is the perfect spot for a tranquil day of sightseeing – sometimes interrupted by the Gregorian chant coming from the Benedictine monks during religious ceremonies.
Surrounded by vineyards, olive groves and hills, the Roman style abbey dates back to the 11th century. Built in precious travertine marble, the story goes that Charlemagne commissioned the construction in 781 to honor the appearance of an angel advising him on the cure to save his soldiers from a pestilence.
Recommended Abbazia di Sant’Antimo hotel: La Casa in Val d’Orcia (rates start at €89 [$99] per night)
Bagno Vignoni (14 miles)
The village of Bagno Vignoni, located on a hill overlooking the Val d’Orcia, attracts many visitors thanks to the abundant hot springs found in the area.
Bagno Vignoni sits in its own unique class when it comes to the hot springs: the main square, Piazza delle Sorgenti, is a natural pool originating in the 16th century. It contains warm, steamy water coming from an underground source of volcanic origins. In other words, there’s a volcanic spring in the center of the village. The water comes from Parco dei Mulini (Park of the Mills), where mills have been operating until the 1950s, even during dry seasons, thanks to the thermal water flow.
Remember to pack a swimsuit – once here, you’ll want to bathe in the balmy waters.
La Bottega di Cacio is a little eatery where you can enjoy tasty local cold cuts, such as Pecorino cheese, wild boar sausage, homemade jams, red wines from neighboring Montepulciano and Montalcino.
Recommended Bagno Vignoni hotel: Albergo Le Terme (rates start at €170 [$190] per night)
Pienza (10 miles)
Last stop of this Tuscany road trip is Pienza. An UNESCO World Heritage Site, this city’s history is entagled with Pope Pio II who was born here when this place was an anonymous village. When he became pope in 1458, he wanted to turn his birthplace into the ideal Renaissance town. The construction started in 1459 and went on for four years, by which time the village had turned into a harmonious 15th century town. Unfortunately, due to his untimely death, the urban reorganization stopped, and Pienza has basically not changed at all since then.
Visit Palazzo Piccolomini, built as a summer residence for the pope and considered an early example of Renaissance urban planning. The palace was chosen by movie director Franco Zeffirelli as a filming location for Romeo and Juliet.
Pienza’s Pecorino cheese has a great reputation among Italian cheese-lovers. They love Pecorino cheese so much here, that there’s an annual festival, Fiera del Cacio, dedicated to it in September.
Recommended Pienza hotel: Hotel Corsignano Pienza (rates start at €86 [$96] per night)