14 Best Places to Visit in Tuscany and Itinerary

Best things to do in Tuscany and our recommended itinerary

To visit Tuscany is to dive into one of the most beautiful regions of Italy, between hilltop villages, famous vineyards and medieval towers. If its capital Florence, jewel of the Renaissance, is one of the essential sites to see in Tuscany, do not neglect the other cities and the countryside, a real postcard image with its famous cypresses. Better to have a vehicle to discover the region. A road trip in Tuscany in slow life mode will allow you to apprehend the Italian Dolce Vita .

What to do in Tuscany? What are the sites not to be missed? Which villages and vineyards to visit? Which itinerary for a road trip? Following my three trips in spring and winter, I give you in this blog article all my advice and tips for a successful stay in Tuscany.

Visit Tuscany on a road trip

The map below will allow you to identify at a glance the must-see sites in Tuscany. I do not address in this guide the province of Livorno (along the Mediterranean) and the island of Elba because they are mainly seaside destinations. My three trips to Tuscany took place outside of the summer.

The ideal way to visit Tuscany is to take a road trip by car or van. Indeed, it will be complicated to get to the smallest villages without a means of transport. The train makes it possible to connect the big cities (Florence, Pisa, Siena and Lucca), but not to reach the perched villages.

If you are not traveling with your vehicle, you can rent one in one of the big cities (at Pisa or Florence airport for example).


I start this guide to Tuscany with the most beautiful city, Florence ( Firenze in Italian), cradle of the Renaissance and the Italian language. The capital of the region is an open-air museum, it alone brings together 25% of the works of Italian artistic heritage. Among the emblematic monuments, do not miss the Duomo and the Baptistery with its pink, white and green marble facade. The city has many museums, the most important of which are the Uffizi Gallery and Galleria dell’Accademia. The first houses Renaissance masterpieces with a set of rooms dedicated to Botticelli. The second is especially visited for its mythical sculpture, Michelangelo’s David.

To avoid spending your time in queues, it is absolutely necessary to book your tickets for the museums you have planned to visit, especially the most famous ones. You will find all the useful information and my advice in my guide to visiting Florence.

How long: 2 days minimum

Accommodation in Florence

  • €75: Lavagnini My Place B&B is one of the best budget accommodations to stay in Florence. It is located in the north just 15 min walk from the historic center and outside the ZTL, convenient if you come by car.
  • €78: B&B The Heart Of Florence, this bed and breakfast type accommodation offers pretty rooms with wooden furniture and ceilings painted with frescoes. Close to all shops and sites to visit.
  • 152 €: V-Rooms All’Angolo Del Duomo, this guest room is located in the heart of the city, 600 meters from the Strozzi Palace in Florence. Parking and breakfast extra.


Great rival of Florence, Siena has an entirely Gothic architecture which contrasts with its neighbor. The historic center, listed as a UNESCO World Heritage Site, has escaped the ravages of time and remains in the same aspect as in medieval times. Siena also has its cathedral (Duomo), it is one of the essential sites to visit in Tuscany. Its interior is simply magnificent, I found it much more beautiful than that of Florence. Siena Cathedral is one of the largest Gothic churches in Italy. Siena has fewer museums and works of art than Florence, but you will discover paintings by artists from the Sienese school.

Apart from the religious sites, don’t miss the piazza del Campo, the city’s central square in the shape of a shell. Every year it hosts the Palio, a famous horse race at the foot of the Palazzo Pubblico and the Torre del Mangia.

How long: 1 day

Accommodations in Siena

  • €87: B&B La Coperta Ricamata, this bed and breakfast is located north of the historic center of Siena, 15 minutes on foot from the station. Rooms with a view of the garden and a hearty breakfast included in the price.
  • €96: B&B Il Corso, this bed and breakfast very well located in the shopping street via Banchi di Sopra is perfect for discovering Siena and its historic center. Also a suite with terrace. Breakfast included.
  • €167: Hotel Santa Caterina, this establishment located in an 18th century villa is located 15 minutes on foot from the historic centre. It has private parking which is convenient if you come by car. Breakfast included.
piazza del campo - Tuscany itinerary - Tuscany things to do


Among the things to do in Tuscany you cannot miss Pisa and its famous leaning tower. It is one of the most visited tourist sites in Italy. But the city does not have the charm of Florence, Siena or Lucca. It is for this reason that many visitors are content with a day trip from a nearby town.

The 3 main monuments which are the Tower of Pisa, the Duomo and the Baptistery are grouped together in Piazza dei Miracoli. A few hours are enough to go around. If you have the time and the desire to discover the city away from the tourists, I invite you to take a walk in the historic city and on the banks of the Arno river. The latter is lined with many palaces with colorful facades. You can possibly spend a night there (as we did), which allows you to enjoy the monuments at the end of the day when most tourists have left.

How long: 1/2 day to 1 day

Accommodations in Pisa

  • €50: Pisacentro Guest House is one of the cheapest places to stay in Pisa. This guesthouse near the station and the airport offers rooms with or without private bathroom. It is ideal for small budgets.
  • €66: Casa San Tommaso, very well located 300 meters from the Tower of Pisa, this guest room set in an 18th century house is very good value for money with breakfast included.
  • €98: La Torre Garbata, located 200 meters from Piazza dei Miracoli, this bed and breakfast offers rooms with a view of the ramparts of Pisa and the baptistery. Some have a nice terrace. Private parking at an additional cost.


In the shadow of the neighboring ultra-tourist towns, Lucca ( Lucca in Italian) is for me the most underrated town in Tuscany. However, this charming medieval city surrounded by ramparts built in the 16th century is well worth a stop during your road trip in Tuscany. The sites to see are mainly religious buildings (cathedrals and churches), medieval towers, an amphitheater-shaped square built on Roman ruins and a palace with an Italian garden.

Lucca can easily be visited from Pisa (30 min) or Florence (1 hour). You can plan to go back during the day if you do not want to spend the night there. If you are tired of the crowds, take a trip to Lucca where the tourists are much less numerous.

How long: 1 day

Accommodation in Lucca

  • €74: Il Vicolo, this bed and breakfast located on the porta Santa Maria side in the north of the old town of Lucca offers double rooms and a kitchen to be shared with the other residents.
  • €97: Residenza Centro Storico, very well located in the heart of the old town and close to Piazza San Michele, this bed and breakfast offers renovated rooms with typical Tuscan antique furniture.
  • €106: Villa San Donato B&B, this accommodation located just outside the city walls is ideal if you come to visit Lucca by car as it has free private parking. Breakfast is included in the price.
Lucca - Tuscany itinerary - Tuscany things to do

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 slow life. You will find many agriturismos along the small roads to make a stop These country inns offer room and board and the food is divine. Alongside farms, vineyards and wine tastings, Chianti is also home to Renaissance villas and castles from the Middle Ages, which further reinforce its postcard image.

If you just travel the roads without stopping at the inns and vineyards, you can visit Chianti in half a day during a stopover between Florence and Siena. But it would be a shame to pass so quickly in this region which is one of the most beautiful in Tuscany.

If you like this type of landscape in the heart of the vineyards, I also advise you to visit the Langhe in Piedmont which are classified as World Heritage by Unesco.

How long: 1 day minimum

Accommodation in Chianti

You will find many agriturismos in Chianti. Many of these structures that advocate slow life offer accommodation from a minimum of 3 nights. I advise you to experience it at least once during your road trip in Tuscany. Here are some excellent addresses to spend a few days in Chianti.

  • 79 €: Agriturismo Crocino in Chianti, this establishment is perfect for travelers on a budget who wish to enjoy a stay on the farm. It is located in Gaiole in Chianti and has a swimming pool. Breakfast is not included.
  • 129 €: Collelungo, this accommodation offers well-equipped apartments for 2 to 4 people with or without a terrace. Located 4 km from Castellina in Chianti, it has an outdoor swimming pool. Breakfast is not included.
  • 204 € : Agriturismo Borgo Il Bonagino, this accommodation located in Radda in Chianti has an outdoor swimming pool. Suite for two or furnished apartment for 3 to 6 people.
Vineyards in Chianti - Tuscany itinerary - Tuscany things to do
Vineyards in Chianti

Saint Gimignano

It is the best-known medieval village in Tuscany, symbolized by its large towers and its double walled enclosure. Originally there were 72 towers, each family wishing to build one higher than the neighbor to assert its wealth and power. Today there are only 14 left and it is possible to climb some towers to enjoy a view of the village of San Gimignano and the surrounding countryside.

Among the sights to see in the medieval lanes, don’t miss the Cathedral ( Collegiata ) in Piazza del Duomo , an 11th  century building covered in frescoes. On the same square, a 12th century palace houses the Museo Civico which includes many paintings. If you plan to visit several museums and buildings, I suggest you take the San Gimignano Pass All Inclusive (13 €) which gives access to all the must-see sites.

I had the opportunity to visit San Gimignano twice. The first in May in the rain and with streets full of tourists. The second was in January with a beautiful sun but a completely deserted village. It is better to avoid winter because many sites and businesses are closed.

How long: 1/2 day

Accommodation in San Gimignano

If you want to take a road trip in Tuscany outside the big cities, staying in San Gimignano can be a good idea. You will enjoy the morning and evening of a village emptied of its tourists who have come on excursions. Many restaurants are present in the village. From San Gimignano it is easy to visit Siena or Volterra.

  • €73: Palazzo Mari, this bed and breakfast located 300 m from the cathedral offers rooms located in a palace. A shared kitchen is available with enough to make breakfast.
  • €84: Modern Apartment, in the old town but far enough away to be quiet, this modern apartment of 70 m² for 2 to 4 people is very comfortable. The host speaks French which is quite practical.
  • €116: Hotel Villa Belvedere, this hotel located just outside the medieval city offers rooms for 2 to 4 people. The big plus is its free private parking (hard to find in the village) and its outdoor swimming pool.
 - Tuscany itinerary - Tuscany things to do


The village of Volterra is 30 km west of San Gimignano. It is easy to visit the two villages in one day from Siena. If you arrived in Siena by train and don’t want to hire a car, this day trip will allow you to discover both villages.

With its medieval walls and buildings, Volterra seems frozen in time. Less overrun with tourists than San Gimignano, the village which was founded by the Etruscans houses a 12th century Roman cathedral and several museums. If you only have to see one museum, I recommend the Museo Etrusco Guarnacci (€8) which brings together one of the finest collections of Etruscan objects 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 have few days to complete your road trip in Tuscany, I advise you to visit only one of the two villages (my preference is San Gimignano).

How long: 1/2 day

Volterra - Tuscany itinerary - Tuscany things to do


Wine lovers know the region, because it is here that the brunello di Montalcino, a red wine with a worldwide reputation, is produced. The village is therefore mainly visited by oenophiles who come to taste different wines in the wine bars (package with 2/3/5 brunello). The major building of Montalcino is its 14th century fortress where you can climb the ramparts. Apart from that the village is relatively small and we cross it quickly.

Montalcino is not one of the must-see places to visit in Tuscany. If you cross the Val d’Orcia by the small roads coming from Siena, I advise you to reach Pienza directly without making the detour to Montalcino.

How long: 1 to 2 hours

Montalcino - Tuscany itinerary - Tuscany things to do

Abbey of Sant’Antimo

This Cistercian abbey built in the Romanesque period enjoys a prime location in the hollow of a hill planted with olive trees and cypresses. It is 10 km south of Montalcino. According to historical accounts, the abbey was founded by Charlemagne in the 9th century. The interior is quite sober and stripped down.

The old treasure room houses the Farmacia Monastica which sells food products made according to the recipes of the ancestral monastic tradition of herbalism (honey, fruit jams, sweets and herbal teas). The pharmacy also offers a selection of body care products based on natural essences and medicinal herbs. In addition, you can taste the Sant’Antimo beer produced according to an exclusive recipe of the Abbey.

The Abbey of Sant’Antimo is open every day from 10 am to 6.30 pm. Free visit or with a guide (€4). Paid parking on site but in January we were alone and did not pay.

How long: 1 hour

Abbey of Sant'Antimo - Tuscany itinerary - Tuscany things to do

Val d’Orcia

It is in this valley crossed by the Orcia river that you will discover some of the postcard landscapes of Tuscany. Of course, I mean the cypress-lined roads that mostly lead to agriturismos. The Val d’Orcia includes the villages of Montalcino, Pienza and Montepulciano. But to discover its superb panoramas you will have to get lost on the small country roads. It is not easy to give precise indications on the spots to see, I simply advise you to get off the main roads during your road trip in Tuscany (especially the SR2). On the other hand, we found that it was not easy to stop to take pictures. The roads are often narrow and there is no parking space.

I will still tell you the most Instagrammable site in Val d’Orcia, the one that everyone wants to take a picture of. This is the small winding road that leads to Agriturismo Baccoleno. But be careful, the site has become very popular, so I’m counting on you not to encroach on private property. The use of drones is prohibited (a sign reminds you everywhere). The viewpoint is at this location 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 gate of the agriturismo. You then have to walk in the field to reach the viewpoint.

How long: 1/2 day

Accommodation in Val d’Orcia

  • €94: La Pievina, this accommodation in the countryside offers large double rooms with excellent value for money for the Val d’Orcia region. Breakfast is also included in the price.
  • €113: Agriturismo Cerreto, located near Pienza, this 15th century farmhouse offers rooms and apartments equipped with a kitchenette for 2 to 6 people. Outdoor pool.
  • 137 €: Agriturismo Baccoleno, the most Instagrammable agriturismo in Val d’Orcia offers 75 m² apartments for 4 people with kitchenette. 4 night minimum stay. Indoor heated swimming pool open all year round.
  • €151: Abbadia Sicille, this accommodation is magnificent, it almost feels like sleeping in a castle, it’s a sure hit! Outdoor swimming pool and breakfast at an additional cost.
Val d'Orcia: the Baccoleno farmhouse - Tuscany itinerary - Tuscany things to do
The Instagram spots of the Val d’Orcia: the Baccoleno farmhouse


We stay in the Val d’Orcia to discover Pienza, a medieval village whose many buildings have been rebuilt in a Renaissance style. It was in 1460 that the future Pope Pius II embarked on the transformation of his native village. He wanted to make Pienza a model city of the Renaissance. Unfortunately his death in 1464 interrupted the work, the palace and the cathedral were never built. The historic center has been listed as a UNESCO World Heritage Site.

Place Pio II is the center of the village and concentrates all the buildings to see. 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 really very small, if you don’t plan to visit the palace or the museum you will do the tour in less than an hour. In season you can have lunch on site (during our trip in January all the restaurants were closed).

How long: 1/2 day

Pienza in Tuscany< - Tuscany itinerary - Tuscany things to do


At the limit between Val d’Orcia and Val di Chiana, the village of Montepulciano is one of the must-see sites to visit in Tuscany. As in Pienza, the architecture is marked by the Renaissance style. The historic center is surrounded by 16th century ramparts . Montepulciano stretches along a main artery that houses several palaces. On the Piazza Grande stands the Palazzo Comunale with its tower (14th century ) and the cathedral (16th century ). Do not hesitate to leave the main street to discover other palaces.

As you can see from the photos, Montepulciano was completely deserted when we were there. Winter is the time when traders take their holidays (January 10 to 23 in 2022) and everything was closed. Luckily we still had the sun! Thanks to its position on a rocky ridge, Montepulciano offers a superb panorama of the Val d’Orcia and the Val di Chiana. It is in Montepulciano that the vino nobile, one of the famous Tuscan wines, is produced.

How long: 1/2 day

Montepulciano - Tuscany itinerary - Tuscany things to do
View of Val di Chiana

Terme di Saturnia

This stopover at the Saturnia thermal baths in southern Tuscany is perfect for taking a relaxing break between village visits. The area is home to natural hot springs as well as a spa establishment.

The best known site is cascate del Mulino (or cascate del Gorello), a waterfall with turquoise water that pours into natural pools. The sulphurous water that gushes out at 37°C has healing properties. This site is very popular on social networks and therefore very popular. But good news, it’s completely free. To get there enter these coordinates, you have to take the small dead end road that starts from the SP10. Several free car parks are available.

On the spot there is nothing arranged, neither showers nor toilets. And for his business you have to leave them at the edge of the waterfall. There is still a bar next to the car park. Please note that the crowds can be very high at the cascate del Mulino. I advise you to go there in the early morning or in the evening because the site is open 24 hours a day, 7 days a week.

1 km north of the waterfalls is the thermal complex with its 5 star hotel Terme di Saturnia Natural Spa. You don’t have to sleep there to enjoy the 5 swimming pools at 37.5°C. The entrance fee is €19 (€24 at weekends) for the day.

How long: 1/2 day to several days

 - Tuscany itinerary - Tuscany things to do


It is the last village to visit on a road trip in Tuscany before continuing to Rome. Pitigliano seems clinging to the cliff, the facades of the houses are integrated into the tuff rock. Before entering the village, you have to stop on the road coming from the south-west at the little Madonna delle Grazie church . It is in this bend that you will enjoy the most beautiful view of Pitigliano. It is particularly pretty at the end of the day when the sun illuminates the facades of the houses of the village.

A large Jewish community that had fled Rome settled in the 16th century in Pitigliano, which earned it the nickname of Little Jerusalem. If you are interested, you can visit the museum retracing the history of this almost extinct Jewish community. It includes, among other things, a tiny synagogue from 1598.

Pitigliano has no particular monuments to see apart from three museums. The idea is rather to stroll through the medieval streets to soak up the atmosphere. On our side we visited the village quickly. Because it must be said that at the end of these few days in Tuscany it seems that all the villages are alike.

How long: 1/2 day

Pitigliano - Tuscany itinerary - Tuscany things to do

What itinerary for a road trip in Tuscany?

Visit Tuscany in 4-5 days

This is the minimum number of days you need to plan to visit Tuscany, unless you are crossing the region at full speed during a larger road trip in southern Italy. With only 4 or 5 days I advise you to devote yourself to the north or south of the region. Florence or Siena are excellent starting points.

  • 4 or 5 day itinerary in northern Tuscany: plan at least 2 days to visit Florence. Leave the next day to discover the Chianti vineyards by car for a day in postcard landscapes. For the 4th day you can reach the beautiful medieval town of Lucca (possible journey by train). The other option is to go to Pisa if you prefer to see the famous leaning tower. In 5 days you can see both cities.
  • Itinerary of 4 or 5 days in the center and south of Tuscany: this itinerary departs from Siena. After spending a day discovering the medieval town, dedicate a day to San Gimignano and Volterra. For your third day, explore the villages of Val d’Orcia (Montalcino, Pienza and Montepulciano). Spend a night in an agriturismo in the middle of the countryside before returning to the village of Pitigliano and a moment of relaxation at the Terme di Saturnia.

Visit Tuscany in 1 week (7 to 8 days)

With a week’s vacation, it is quite possible to do all the sites that I have presented in this guide to Tuscany. If you come by plane, first join the city of Pisa (many low-cost flights) before renting a car for the rest of the week. Be aware that the beginning of the route (Pisa, Lucca, Florence and Siena) can easily be done by train. In this case I suggest that you only rent a rental car for the second part of the trip.

  • Day 1: After reaching the city of Pisa by plane or train, spend the rest of the day visiting its must-see monuments.
  • Day 2: Set sail for Lucca to visit this charming medieval town.
  • Day 3 and 4: two days are necessary to visit Florence and its many museums.
  • Day 5: The Chianti vineyards and the villages of San Gimignano and Volterra will occupy your day.
  • Day 6: spend the day visiting the monuments of Siena including its superb cathedral.
  • Day 7: discover the Val d’Orcia and the villages of MontalcinoPienza and Montepulciano.
  • Day 8: if you have a little time left before returning, relax at the Terme di Saturnia and then visit Pitigliano.

Practical information for visiting Tuscany

How to get to Tuscany

Pisa is one of the best gateways to come and visit Tuscany. Its airport, which hosts many low-cost flights, allows you to travel at low prices. On our side we came with our car because Pisa is only 4 hours away from Nice where we live. The city is also well served by train.

The other solution is to go through Florence airport. The advantage is that you can easily visit Pisa and Lucca in the day by train and thus stay in the same accommodation in Florence for several days.

Car rental

To get out of the big cities and discover the Tuscan countryside, a rental car will be essential. Getting lost on the small country roads, taking advantage of the last rays of the sun to take photos and spending the night in one of the many agriturismos are activities only possible if you have a vehicle. Tuscany can also be discovered on a road trip and it will be a shame to confine yourself to the cities, especially if you have a museum overdose.

Beware of speed cameras, there are almost everywhere on the roads of Tuscany. Although I’m always careful I still managed to get flashed. Barely 3 km/h over the limit, it cost me €47.40 to pay by bank transfer. As it is our vehicle, the fine arrived 3 months later by registered mail in France.

ZTL (limited traffic zone)

Before going on a trip to Italy, you must understand the principle of the ZTL (z ona a traffico limitato in Italian). The city centers of Pisa, Siena, Lucca, Florence and certain villages are prohibited for vehicles without authorization. And as a tourist, the only possibility of crossing the ZTL by car is to have accommodation within the zone. In this case, your hotel will complete a form with your contact details and the registration of your vehicle to send it to the town hall.

The ZTLs are always indicated by signs (in Italian) and the cameras present should alert you. To avoid a fine of €100, park in the car parks located just before.

When to visit Tuscany

The high season for visiting Tuscany is from May to October. This is the best period for the weather, but also the time when the attendance is the most important and when the prices of accommodation are at their maximum.

On our side we visited Tuscany in winter. The weather was superb (bright sunshine all the time), it wasn’t too cold during the day and above all there were hardly any tourists (may also be due to Covid-19). In the big cities (Siena, Florence or Pisa) the tourist sites were all open, as well as the restaurants and shops (in addition it is the sales in January). Going out of season allowed us to benefit from attractive rates for accommodation.

On the other hand, choosing winter for a stay in Tuscany is not necessarily a good idea if you plan to leave the big cities. In the small villages almost everything was closed in January (this is the period when traders take their holidays). So unless you like deserted villages, it is better to come between May and October.

When in the countryside on the Chianti or Val d’Orcia side the landscapes are not as green as in spring and summer and there are no grapes in the vineyards.

Ready to go visit Tuscany? If you have any questions about the organization of your road trip or stay, do not hesitate to ask them in the comments of the blog.

Camille L.

Passionate about foreign languages, cooking and writing. I wish to share with you the places, the meetings and the gastronomic discoveries which gave relief to my travels.

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