Tuscany has always been one of my dream destinations because of the awesome scenic pictures I have seen. Finally, I made a trip to Tuscany myself and here are my suggestions of 7 beautiful towns plus stunning Sienna to include in your Tuscany road trip. One of the ways to do it is a road trip starting and ending in Florence but you can decide to do it in another way. The first region you enter going south from Florence is Chianti. You will be following one of the most scenic roads in the area: the Via Chiantigiana stretching from Florence all the way to Siena. You’ll just be making little derogations to visit some of the towns on this itinerary. Find picture perfect views of that landscape on your way. Then continue your journey through UNESCO listed Val d'Orcia up to Montepulciano. The numerous picturesque villages and towns along the way invite for spontaneous stopovers.
So let’s go and see all of it! Our first stop is Greve in Chianti.
Greve in Chianti
Greve is a small town with a quaint atmosphere with many shops and restaurants. Greve's history is connected to the beautiful Castle of Montefioralle located above the town. It served as the castle's marketplace in the 13th century. The strategic position at the crossroads of three important pilgrimage roads (the Chiantigiana road, the road to Valdarno and the road to Val di Pesa) favoured its economic growth. Piazza Matteotti (square) is the focal point of the town. The portico of the square serves as a frame for boutique shops, artisans’ workshops and restaurants. If you can choose the day of your visit I recommend Saturday because of the market taking place on Saturdays with plenty of stalls with fresh fruit and veggies, cheese, olives, household goods, flowers and a bit of fashion!
Panzano in Chianti
As you walk the silent streets of the charming Panzano, you are truly immersed in another time. Follow the paved road and you will find many little shops that exhibit artwork and local artisans. Visit the impressive church of Santa Maria Assunta, rebuilt in the 19th century on top of the medieval building with awesome stone stairway incorporating a tower for the long destroyed castle.
Castellina in Chianti
The spectacular drive out to this almost hidden Chianti landmark is a good reason to visit its cobbled stone streets. Castellina offers a long history, reaching back to the Bronze age and till today, and as producer of wine and olive oil too. The main fortification is called the Rocca and its huge 14th-century tower has a magnificent view over the town and the surrounding countryside. Along the ancient walls, there lays an impressive underground tunnel called Via Della Volte, which is lined with shops, artisans and restaurants. The tunnel goes around the city, making for a cool and refreshing escape from the summer sun. This unique formation is divided by the main street, Via Ferruccio, housing boutique shops, workshops, cafes and Palazzo Banciardi and Palazzo Squarcialupi. The Church of San Salvatore deserves a visit. It was rebuilt after WWII, displaying a valuable fresco by Lorenzo Bicci depicting the Virgin Mary with Child.
Monteriggioni is one of the most impressive walled medieval towns in Tuscany. It’s a typical fortified village that started its life as a castle at the beginning of the 13th century. Today its mighty towers can still be seen for miles. The towers once impressed Dante Alighieri so much that in his Divine Comedy he compared them to “horrific giants”. Today Monteriggioni has preserved its medieval character. Its cobbled streets haven’t seen much change over the passing centuries, and its city walls are still intact. You can take a short walk along the city walls thanks to the recently added walkway.
Sienna is located in between Monteriggioni and Montalcino and is too awesome so it deserves a special post, check it out here. In any case, make sure you take enough time to enjoy all of its beauty.
The 14th-century Montalcino is located on the colourful hills of the Val d’Orcia. Montalcino offers a panoramic view of the beautiful Asso, Orcia and Ombrone valleys. The town is known because of its production of one of Italy’s finest red wines Brunello di Montalcino. Brunello di Montalcino, alongside Chianti, is one of the most prestigious of all Italian wines. The wine is made exclusively from Sangiovese grapes grown in Montalcino. Brunello translates roughly as 'little dark one'. In addition to exquisite wines, the countryside around Montalcino produces honey, extra-virgin olive oil, meats and cheeses, all of which can be enjoyed in one of the atmospheric restaurants and wine bars in the area. Montalcino is dominated by an imposing fortress and blessed with an impressive history. The Fortress was first built in the middle of the 14th century in the shape of a pentagon. Get into the Fortress and walk its ramparts. There’s a splendid view from the top and an enoteca for wine-tasting opportunities. The atmospheric streets of the town centre are perfect for a stroll with little food shopping and wine tasting. Check also the late 13th century town hall with a slender structure flanked by a tall bell tower. The Church of Madonna del Soccorso is worth visiting. It was built in the early 14th century, with expansion finished in the early 17th century. Inside, you can see awesome Baroque altars.
Pienza is a well-known town of the Val d’Orcia and is famous for being the hometown of Pope Pius II, born in 1405. Pius II, with help of architect Bernardo Rossellino, transformed his home town into an architectural jewel. In just four years the harmonious 15th century appearance of Pienza was developed. It is considered to be the incarnation of the Renaissance utopia of an ideal city. Indeed, after those four years, Pienza has largely remained unchanged. Pienza is one of the few remaining Renaissance towns in Italy. It has obtained recognition as a UNESCO World Heritage Site in 1996. The town is small and it is easy to walk around without much effort. Pienza offers views of incomparable beauty, to be captured in great photographs! Start your visit of Pienza from the famous Piazza Pio II, where Palazzo Piccolomini is located. You will appreciate its facade with a huge entrance and the inner courtyard with a truly magnificent view overlooking much of the valley. The stunning Cathedral of Santa Maria Assunta impresses with a travertine facade and an apparent decorative simplicity. The church boasts works selected personally by Pius II and commissioned to the best Siena artists. After admiring it, walk the fabulous streets of Pienza and take your time for a coffee or meal.
Standing high atop a hill in southern Tuscany, Montepulciano is a medieval town of rare beauty, highly recommended for a visit in Tuscany. The town is located at an altitude of 600 meters, perched on top of a limestone ridge. You can find elegant Renaissance palaces, ancient churches and awesome squares in this charming town. Enjoy vast panoramas all over the wonderful Val d'Orcia and Val di Chiana valleys surrounding Montepulciano. A walk through Montepulciano is the best way to view the town and enjoy stunning views of the surrounding countryside covered by vineyards producing the famous Nobile vine! Montepulciano has received great attention following the filming of the vampire saga Twilight sequel New Moon here. Piazza Grande is the heart of Montepulciano and the setting for its main events, including the barrel-racing Bravio delle Botti contest held annually in August. The Duomo, or Cathedral of Santa Maria Assunta located on the Piazza Grande, was built in the 17th century and has beautiful interiors, decorated with many artworks. The sanctuary of the Madonna di San Biagio is in a walking distance from the town. It is well worth visiting. The sanctuary was built in a Tuscan style in the 16th century. It has a circular shape with a large dome over a terrace. The façade is made of white travertine and features two large bell towers.When visiting this awesome part of Tuscany, take the opportunity to use the healing power of thermal waters of Tuscany with a much deserved break at San Giovanni Terme Rapolano.
San Giovanni Terme Rapolano
Rediscover the pleasures for your senses indulging in relaxing five thermal pools set in the stunning countryside. The precious spring waters bubbling up from the ground at San Giovanni have notable therapeutic properties. I recommend staying overnight in their hotel to take the opportunity to fully enjoy all of the thermal pools and grounds because some of them are only available for hotel guests.Had a great time? Just a few final remarks before moving on.
Where to stay in Tuscany?
When you travel by car and want to do wine tasting as well, it’s a matter of strategy to choose your accommodation wisely. I can’t say that I was very lucky in this sense.
I stayed at Villa Casalecchi near Castellina in Chianti, which was awesome and surrounded by vineyards but did not offer wine tasting for individual travellers.I think it’s worth considering a stay at Montalcino because there are many places in town offering wine tasting, so maybe it’s an option to consider. I also stayed at Hotel Corsignano Pienza during my trip.
It was a great hotel with really awesome views to Val d’Orcia but also not much luck for wine tasting in Pienza, so better to inquire in advance about the wine tasting opportunities not to be disappointed later.
Distances and travel times between towns of Tuscany by car
Florence to Greve in Chianti 33 kilometres, 1 hour
Greve in Chianti to Panzano in Chianti 8 kilometres, 10 minutes
Panzano in Chianti to Castellina in Chianti 20 kilometres 30 minutes
Castellina in Chianti to Monteriggioni 37 kilometres 50 minutes
Monteriggioni to Siena 20 kilometres 20 minutes
Siena to Montalcino 40 kilometres 50 minutes
Montalcino to Pienza 23 kilometres 30 minutes
Pienza to Montepulciano 15 kilometres 20 minutes
Montepulciano to Sangiovanni Terme Rapolano 40 kilometres 40 minutes
Sangiovanni Terme Rapolano to Florence 100 kilometres 1, 5 hours
Like it? Pin it!
Bonus tip: If you have more time include city number 9 in your itinerary: Arezzo.
You might find helpful a guide for planning your trip to Italy.
What did you think? Have you been to Tuscany? Or perhaps you’re thinking of visiting there in the near future? Either way, I’d love to hear from you so please add your comments below.
Author: Anita Sāne
About the author
Anita is a part-time traveler, passionate photographer and a mature career woman from Latvia, traveling mostly solo for more than 10 years. She is a skilled travel planner planning and executing her travels by herself. Anita wants to show you how to travel the world and open your mind to new experiences. Follow her also on Instagram, Pinterest, Twitter and Bloglovin.