Visiting Tuscany means diving into one of the most beautiful regions of Italy, with hilltop villages, famous vineyards, and medieval towers. While its capital, Florence, a jewel of the Renaissance, is one of the must-see places in Tuscany, don’t overlook the other towns and the countryside, a true postcard landscape with its iconic cypress trees. It’s best to have a vehicle to explore the region. A slow-life road trip in Tuscany will allow you to experience the Italian Dolce Vita.
What to do in Tuscany ? Which places should you not miss ? Which villages and vineyards should you visit ? What itinerary should you follow for a road trip ? After three trips in spring and winter, I’m sharing in this blog article all my tips and recommendations to help you plan your trip to Tuscany.
Things to do in Tuscany on a road trip : the map
The map below will allow you to quickly spot the must-see places in Tuscany. In this guide I do not cover the province of Livorno Province (along the Mediterranean) or Elba Island, as these destinations are mainly focused on seaside tourism. My three trips to Tuscany all took place outside the summer season.
The best way to visit Tuscany is to take a road trip by car or van. Indeed, it will be difficult to reach the smaller villages without a means of transport. Trains connect the main cities (Florence, Pisa, Siena, and Lucca), but they do not reach the hilltop villages.
If you are not traveling with your own vehicle, you can rent one in one of the major cities (for example at the airport in Pisa or Florence). To find the best price, I recommend using this car rental comparison site.
Florence
I start this Tuscany guide with the most beautiful city : Florence (Firenze in Italian), the cradle of the Renaissance and of the Italian language. The capital of the region is an open-air museum and alone contains 25% of Italy’s artistic heritage. Among the iconic monuments, don’t miss the Duomo and the Baptistery with their pink, white, and green marble façade. The city has many museums, the most important being the Uffizi Gallery and the Galleria dell’Accademia. The first houses Renaissance masterpieces with several rooms dedicated to Sandro Botticelli. The second is mainly visited for its mythical sculpture, the David by Michelangelo.
To avoid spending your time in lines, you absolutely need to book your museum tickets in advance, especially for the most famous ones. Look at this Florence Pass.
How long : at leat 2 days
Accommodations in Florence
You can find more accommodations and tips in my guide where to stay in Florence. |
Siena
The great rival of Florence, Siena has entirely Gothic architecture that contrasts with its neighbor. The historic center, listed as a UNESCO World Heritage Site, has escaped the ravages of time and still looks much the same as it did in the medieval period. Siena also has its own cathedral (Duomo), one of the must-see sites in Tuscany. Its interior is simply magnificent, I found it far more beautiful than Florence’s. Siena Cathedral is one of the largest Gothic churches in Italy. Siena has fewer museums and artworks than Florence, but you will discover paintings by artists of the Sienese school.
Aside from religious sites, don’t miss the Piazza del Campo, the city’s shell-shaped central square. Each year it hosts the Palio di Siena, a famous horse race at the foot of the Palazzo Pubblico and the Torre del Mangia.
How long : 1 day
Accommodations in Siena
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Pisa
Among the things to do in Tuscany, you can’t miss Pisa and its famous leaning tower. It is one of the most visited tourist sites in Italy. However, the city does not have the charm of Florence, Siena, or Lucca. For this reason, many visitors simply make a day trip from a nearby city.
The three main monuments, the Leaning Tower of Pisa, the Pisa Cathedral, and the Pisa Baptistery, are all located in the Piazza dei Miracoli. A few hours are enough to see them. If you have time and want to discover the city away from the tourists, I suggest strolling through the historic center and along the banks of the Arno River. It is lined with many palaces featuring colorful façades. You might even spend a night there (as we did), which allows you to enjoy the monuments in the evening once most tourists have left.
How long : half a day to 1 day
Accommodations in Pisa
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Lucca
In the shadow of its ultra-touristy neighboring cities, Lucca is, in my opinion, the most underrated city in Tuscany. Yet this charming medieval town, surrounded by walls built in the 16th century, absolutely deserves a stop on your Tuscany road trip. The main attractions are religious buildings (cathedrals and churches), medieval towers, a square shaped like an amphitheater built on Roman ruins, and a palace with an Italian garden.
Lucca is easy to visit from Pisa (30 minutes) or Florence (1 hour). You can consider making a day trip if you do not want to spend a night there. If you’re tired of crowds, head to Lucca where tourists are far fewer.
It is also possible to visit Lucca and Pisa from Florence with this day trip. It includes bus transportation, guided tours with tickets, and a tasting of Buccellato (a traditional cake from Lucca).
How long : 1 day
Accommodations in Lucca
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Visiting Tuscany by hot air balloon
Would you like to visit Tuscany in a unique way ? Experience something truly extraordinary? Then I highly recommend this hot air balloon flight over Tuscany. The one-hour flight passes over the valleys and hills of San Casciano in Val di Pesa in Tuscany. It’s an opportunity to enjoy superb views of castles perched on hilltops and vineyards. A glass of champagne is offered upon landing. The meeting point is directly in San Casciano Val di Pesa.
Chianti Vineyards
It is in this hilly region covered with vineyards that the famous Chianti is produced, a red wine protected by the DOP label. This whole part of Tuscany between Florence and Siena invites you to embrace the slow life. You will find many agriturismo along the small country roads where you can stop. These countryside inns offer accommodation and meals, and the food is absolutely delicious. In addition to farms, vineyards, and wine tastings, the Chianti region is also home to Renaissance villas and medieval castles, which further reinforce its postcard-perfect image.
If you simply drive through the roads without stopping at inns and vineyards, you can visit Chianti in half a day during a stop between Florence and Siena. However, it would be a shame to pass so quickly through this region, which is one of the most beautiful in Tuscany.
How long : 1 day
Where to stay in Chianti ?You will find many agriturismo in the Chianti region. Many of these slow-life oriented accommodations offer stays starting from a minimum of three nights. I recommend trying this experience at least once during your Tuscany road trip. Here are some excellent places to spend a few days in Chianti.
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Visiting the vineyards without a car
For those traveling by train or bus, it is possible to visit Tuscany and the Chianti vineyards without a car from the major cities. I particularly recommend the following activities.
- From Florence : Chianti Wineries Tour with Wine Tasting
- From Siena : Chianti Wine Tour with Lunch
- From Pisa or Lucca : Half-Day Tuscany Chianti Wine Tasting
Visiting the vineyards by car
Even when traveling with your own vehicle, it is best to avoid arriving at a winery without notice. That is why I recommend booking your visit in advance. Here are a few winery visit ideas (you must go directly to the location) :
- Near Radda in Chianti you can book this tasting where you will sample five different products (red wine, white wine, sparkling wine, cured meats, and cheese served with bread and olive oil).
- 18 km from Florence you can book this visit to the Chianti Colli Fiorentini winery where you will taste three different types of wine and bread with extra virgin olive oil.
- In Barberino Tavarnelle, if you would like to combine wine discovery with a true Tuscan dinner, I recommend this tasting of four wines accompanied by local dishes.
San Gimignano
This is the most famous medieval village in Tuscany, symbolized by its tall towers and double ring of walls. Originally there were 72 towers, as each family wanted to build one taller than their neighbors to demonstrate their wealth and power. Today only 14 remain, and it is possible to climb some of the towers to enjoy a panorama over the village of San Gimignano and the surrounding countryside.
Among the sites to see in the medieval streets, don’t miss the cathedral (Collegiata) on Piazza del Duomo, an 11th-century building covered with frescoes. On the same square, a 12th-century palace houses the Museo Civico, which contains numerous paintings. If you plan to visit several museums and monuments, I suggest buying the San Gimignano Pass All Inclusive (€13), which provides access to all the must-see sites.
I have had the opportunity to visit San Gimignano twice. The first time was in May, in the rain and with streets full of tourists. The second time was in January with beautiful sunshine but a completely deserted village. It is better to avoid winter because many sites and shops are closed.
Those who do not have much time to visit Tuscany can choose this excursion from Florence that allows you to visit Pisa, Siena, and San Gimignano in one day (lunch included).
How long : half a day
Where to stay in San Gimignano ?If you want to do a Tuscany road trip outside the major cities, staying in San Gimignano can be a good idea. You will enjoy the village in the morning and evening once it has been emptied of day-trip tourists. Many restaurants are located in the village. From San Gimignano it is easy to visit Siena or Volterra.
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Volterra
The village of Volterra is located 30 km west of San Gimignano. It is easy to visit both villages in one day from Siena. If you arrived in Siena by train and do not want to rent a car, this day trip will allow you to discover both villages.
With its walls and medieval buildings, Volterra seems frozen in time. Less crowded with tourists than San Gimignano, the village founded by the Etruscans is home to a 12th-century Romanesque cathedral and several museums. If you only visit one museum, I recommend the Museo Etrusco Guarnacci (€8), which houses one of the finest collections of Etruscan artifacts in Italy. All the archaeological objects come from excavations carried out in the region.
Volterra and San Gimignano are similar in terms of medieval architecture. If you only have a few days for your Tuscany road trip, I recommend visiting just one of the two villages (my preference goes to San Gimignano).
How long : half a day
Montalcino
Wine lovers know the region because this is where Brunello di Montalcino, a world-renowned red wine, is produced. The village is therefore mainly visited by wine enthusiasts who come to taste different vintages in wine bars (packages with 2/3/5 Brunello). The main monument in Montalcino is its 14th-century fortress, where you can climb the ramparts. Aside from that, the village is relatively small and can be crossed quickly.
Montalcino is not one of the must-see sites in Tuscany. If you are driving through the Val d’Orcia on the small roads coming from Siena, I recommend heading directly to Pienza without making the detour to Montalcino.
Wine lovers will enjoy visiting a private cellar in Montalcino with tasting and appetizers (five different wines including Brunello di Montalcino).
How long : 1 to 2 hours
Abbazia di Sant’Antimo
This Cistercian abbey built during the Romanesque period enjoys a prime location nestled in a hill planted with olive trees and cypress trees. It is located 10 km south of Montalcino. According to historical accounts, the abbey was founded by Charlemagne in the 9th century. The interior is quite simple and austere.
The former treasury room now houses the Farmacia Monastica, which sells food products made according to traditional monastic herbalist recipes (honey, fruit jams, sweets, and herbal teas). The pharmacy also offers a selection of body care products made from natural essences and medicinal herbs. In addition, you can taste the Sant’Antimo beer produced according to an exclusive recipe from the abbey.
The Abbazia di Sant’Antimo is open every day from 10:00 a.m. to 6:30 p.m. Visit free of charge or with a guide (€4). Paid parking on site, but in January we were alone and did not have to pay.
How long : 1 hour
Val d’Orcia
It is in this valley crossed by the Orcia River that you will discover some of Tuscany’s postcard landscapes. I am of course referring to the roads lined with cypress trees that most often lead to agriturismo. The Val d’Orcia includes the villages of Montalcino, Pienza, and Montepulciano. But to discover its superb panoramas you will need to wander along the small country roads. It is not easy to give precise directions for the viewpoints; I simply recommend leaving the main roads during your Tuscany road trip (especially the Strada Regionale 2). However, we found that it was not easy to stop to take photos. The roads are often narrow and there is no place to park.
I will still point out the most Instagrammable location in the Val d’Orcia, the one everyone wants to photograph. It is the winding road leading to Agriturismo Baccoleno. However, the site has become very popular, so please respect the private property. The use of drones is prohibited (a sign reminds visitors everywhere). The viewpoint is located at this spot on the road between the villages of Asciano and Val d’Asso (route from Siena to Pienza). It is possible to park along the road a few meters after the entrance that leads to the agriturismo gate. You then have to walk through the field to reach the viewpoint.
How long : half a day
Where to stay in Val d’Orcia ?
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Pienza
We remain in the Val d’Orcia to discover Pienza, a medieval village where many buildings were rebuilt in a Renaissance style. In 1460 the future pope Pope Pius II began transforming his birthplace. He wanted to make Pienza a model Renaissance town. Unfortunately his death in 1464 halted the work, and the palace and cathedral were never completed. The historic center has been listed as a UNESCO World Heritage Site.
Piazza Pio II is the center of the village and concentrates all the main monuments. It is surrounded by the Palazzo Piccolomini (entrance €7), which was the pope’s residence, the duomo, and the Palazzo Vescovile, which houses a museum. Pienza is very small ; if you do not plan to visit the palace or the museum, you can walk around it in less than an hour. In high season you can have lunch there (during our January trip all the restaurants were closed).
How long : half a day
Montepulciano
On the border between the Val d’Orcia and the Val di Chiana, the village of Montepulciano is one of the must-see sites in Tuscany. As in Pienza, the architecture is marked by the Renaissance style. The historic center is surrounded by 16th-century walls. Montepulciano stretches along a main street lined with several palaces. On Piazza Grande stands the Palazzo Comunale with its tower (14th century) and the cathedral (16th century). Don’t hesitate to leave the main street to discover other palaces.
As you can see in the photos, Montepulciano was completely deserted during our stay. Winter is the time when shop owners take their holidays (January 10 to 23 in 2022) and everything was closed. Fortunately, we still had sunshine ! Thanks to its position on a rocky ridge, Montepulciano offers a superb panorama over the Val d’Orcia and Val di Chiana.
It is in Montepulciano that Vino Nobile, one of the famous Tuscan wines, is produced. Don’t miss a wine tasting and cellar tour. Montepulciano, Pienza, and the vineyards of the Val d’Orcia can be visited from Siena with this excursion.
How long : half a day
Terme di Saturnia
This stop at the Terme di Saturnia in southern Tuscany is perfect for taking a relaxing break between village visits. The region is home to natural hot springs as well as a thermal spa complex.
The most famous site is the Cascate del Mulino (also called Cascate del Gorello), a turquoise waterfall that flows into natural pools. The sulfurous water that emerges at 37 °C has healing properties. This site is very popular on social media and therefore very busy. But the good news is that it is completely free. To get there, enter these coordinates and take the small dead-end road that branches off the SP10. Several free parking areas are available.
There are no facilities on site, no showers or toilets. For your belongings, you have to leave them beside the waterfall. There is however a bar next to the parking area. Be aware that Cascate del Mulino can be crowded. I recommend going early in the morning or in the evening, as the site is open 24/7.
1 km north of the waterfalls is the thermal complex with its 5-star hotel Terme di Saturnia Natural Spa & Golf Resort. You do not have to stay overnight to enjoy the five pools at 37.5 °C. The entrance fee is €19 (€24 on weekends) for the day.
How long : half a day to several days
Pitigliano
This is the last village to visit during a Tuscany road trip before continuing toward Rome. Pitigliano appears to cling to the cliff, with the facades of its houses integrated into the tuff rock. Before entering the village, you should stop on the road coming from the southwest at the small church Madonna delle Grazie. It is at this bend in the road that you will enjoy the most beautiful viewpoint over Pitigliano. It is particularly beautiful at the end of the day when the sun illuminates the facades of the village houses.
A large Jewish community that had fled Rome settled in Pitigliano in the 16th century, which earned it the nickname “Little Jerusalem.” If this interests you, you can visit the museum that traces the history of this almost extinct Jewish community. It includes, among other things, a tiny synagogue dating from 1598.
Pitigliano does not have any particular monuments to see aside from three museums. The idea is rather to wander through the medieval streets and soak up the atmosphere. On our side, we visited the village quite quickly. After several days in Tuscany, it begins to feel like all the villages look alike.
How long : half a day
Best itinerary for a Tuscany road trip
Things to do in Tuscany in 4-5 days
This is the minimum number of days you should plan to visit Tuscany, unless you are simply crossing the region quickly during a larger road trip in southern Italy. With only 4 or 5 days, I recommend focusing on either the north or the south of the region. Florence or Siena are excellent starting points.
4–5 day itinerary in northern Tuscany : plan at least 2 days to visit Florence. The next day, drive to discover the Chianti vineyards for a full day in postcard landscapes. On the fourth day you can head to the beautiful medieval city of Lucca (train connection possible). Another option is to go to Pisa if you prefer to see the famous Leaning Tower. In 5 days you can see both cities.
4–5 day itinerary in central and southern Tuscany : this itinerary starts from Siena. After spending a day discovering the medieval city, devote a day to San Gimignano and Volterra. On your third day, explore the villages of the Val d’Orcia (Montalcino, Pienza, and Montepulciano). Spend a night in an agriturismo in the countryside before heading to Pitigliano and enjoying a relaxing moment at Terme di Saturnia.
Things to do in Tuscany in 1 week (7-8 days)
With one week of vacation, it is entirely possible to visit all the sites I presented in this Tuscany guide. If you arrive by plane, first head to the city of Pisa (many low-cost flights) before renting a car for the rest of the week. However, note that the beginning of the route (Pisa, Lucca, Florence, and Siena) can easily be done by train. In that case, I suggest renting a car only for the second part of the trip.
- Day 1 : after reaching Pisa by plane or train, spend the rest of the day visiting its must-see monuments.
- Day 2 : head to Lucca to visit this charming medieval city.
- Day 3 and 4 : two days are needed to visit Florence and its many museums.
- Day 5 : the Chianti vineyards and the villages of San Gimignano and Volterra will fill your day.
- Day 6 : devote the day to visiting Siena’s monuments, including its superb cathedral.
- Day 7 : set off to discover the Val d’Orcia and the villages of Montalcino, Pienza, and Montepulciano.
- Day 8 : if you still have some time before returning, relax at the Terme di Saturnia and then visit Pitigliano.
Tips and travel guide for visiting Tuscany
How to Get to Tuscany ?
Pisa is one of the best gateways for visiting Tuscany. Its airport, which welcomes many low-cost flights, makes it possible to travel at affordable prices. We personally came by car because Pisa is only a 4-hour drive from Nice where we live. The city is also well served by train.
Another option is to arrive via Florence Airport. The advantage is that you can easily visit Pisa and Lucca on day trips by train and therefore stay in the same accommodation in Florence for several days. In any case, I recommend comparing prices on Skyscanner to see which route is the most interesting depending on the itinerary you have planned.
Car rental
To leave the major cities and discover the Tuscan countryside, a rental car will be essential. Getting lost on the small country roads, enjoying the last rays of sunshine to take photos, and spending the night in one of the many agriturismo are activities that are only possible if you have a vehicle. Tuscany is also best discovered on a road trip, and it would be a shame to limit yourself to the cities, especially if you start getting museum fatigue.
Before renting your vehicle, I recommend comparing prices on this site. Rates can be up to 25% cheaper than booking directly through the major rental companies, allowing you to save money on your stay in Tuscany.
Be careful of speed cameras, as there are many on the roads of Tuscany. Even though I always try to pay attention, I still managed to get flashed (just like during our trip to the Cinque Terre). Only 3 km/h above the limit cost me €47.40, which I had to pay by bank transfer. Since it was our own vehicle, the fine arrived three months later by registered mail.
ZTL (Limited Traffic Zone)
Before traveling to Italy, it is important to understand the principle of the ZTL (zona a traffico limitato in Italian). The city centers of Pisa, Siena, Lucca, Florence, and some villages are closed to vehicles that do not have authorization. As a tourist, the only way to enter the ZTL by car is if you have accommodation inside the zone. In that case, the hotel will fill out a form with your details and your vehicle registration to send to the town hall.
ZTL areas are always indicated by signs (in Italian), and the cameras present should alert you. To avoid a fine of around €100, park in the parking lots located just before the zone.
Best time to visit Tuscany
The high season for visiting Tuscany runs from May to October. It is the best period in terms of weather, but also the time when tourist numbers are highest and accommodation prices are at their peak.
For our part, we visited Tuscany in winter. The weather was superb (sunny all the time), it was not too cold during the day, and above all there were almost no tourists. In the major cities (Siena, Florence, or Pisa), tourist sites were all open, as well as restaurants and shops (and January is also the sales season). Traveling in the off-season allowed us to benefit from attractive accommodation prices.
However, choosing winter for a stay in Tuscany is not necessarily a good idea if you plan to leave the major cities. In the small villages almost everything was closed in January (this is when shop owners take their holidays). So unless you enjoy deserted villages, it is better to come between May and October.
As for the countryside in Chianti or the Val d’Orcia, winter landscapes are not as green as in spring and summer, and there are no grapes on the vines.
Ready to go visit Tuscany ? If you have questions about organizing your road trip or stay, feel free to ask them in the blog comments.