8 Tuscany towns to include in your road trip itinerary

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 south of 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. Enjoy picture-perfect views 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.

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10tuscany road views thesanetravel.com 145078413tuscany road views thesanetravel.com 1450999So let’s go and see all of it! Ready? Pick up your rental car from one of the best car rental companies and start your journey! 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 the market takes place on Saturdays with plenty of stalls with fresh fruit and veggies, cheese, olives, household goods, flowers and a bit of fashion!

110greve in chianti tuscany thesanetravel.com 1440904111greve in chianti tuscany thesanetravel.com 1440913112greve in chianti tuscany thesanetravel.com 1440905114greve in chianti tuscany thesanetravel.com 1440924115greve in chianti tuscany thesanetravel.com 1440919116greve in chianti tuscany thesanetravel.com 1440934Panzano 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 an awesome stone stairway incorporating a tower for the long destroyed castle.

130panzano in chianti tuscany thesanetravel.com 1450016131panzano in chianti tuscany thesanetravel.com 1440942132panzano in chianti tuscany thesanetravel.com 1440955133panzano in chianti tuscany thesanetravel.com 1440951134panzano in chianti tuscany thesanetravel.com 1440960135panzano in chianti tuscany thesanetravel.com 1440963136panzano in chianti tuscany thesanetravel.com 1440962137panzano in chianti tuscany thesanetravel.com 1440982Castellina 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 the 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.

141castellina in chianti tuscany thesanetravel.com 1450021142castellina in chianti tuscany thesanetravel.com 1450027143castellina in chianti tuscany thesanetravel.com 1450025145castellina in chianti tuscany thesanetravel.com 1450040146castellina in chianti tuscany thesanetravel.com 1450043147 castellina in chianti tuscany thesanetravel.com 1450055Monteriggioni

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.

40 monteriggioni tuscany thesanetravel.com 145023541monteriggioni tuscany thesanetravel.com 145017844 monteriggioni tuscany thesanetravel.com 145020444monteriggioni tuscany thesanetravel.com 145018645monteriggioni tuscany thesanetravel.com 145018945monteriggioni tuscany thesanetravel.com 145020146monteriggioni tuscany thesanetravel.com 145019347monteriggioni tuscany thesanetravel.com 1450195Sienna

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.

21siena tuscany thesanetravel.com 1450301Montalcino

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.

19montalcino tuscany thesanetravel.com 145096520montalcino tuscany thesanetravel.com 145090121montalcino tuscany thesanetravel.com 145090322montalcino tuscany thesanetravel.com 145092523montalcino tuscany thesanetravel.com 145091426montalcino tuscany thesanetravel.com 145094030montalcino tuscany thesanetravel.com 145095932montalcino tuscany thesanetravel.com 145097233montalcino tuscany thesanetravel.com 1450974Pienza

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 hometown 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.

70pienza tuscany thesanetravel.com 146003771 pienza tuscany thesanetravel.com 146010672 pienza tuscany thesanetravel.com 146010273pienza tuscany thesanetravel.com 146004671pienza tuscany thesanetravel.com 146004075 pienza tuscany thesanetravel.com 146009377pienza tuscany thesanetravel.com 146010878 pienza valley view tuscany thesanetravel.com 1460112Montepulciano

Standing high atop a hill in southern Tuscany, Montepulciano is a medieval town of rare beauty, highly recommended for a visit to 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. 160montepulciano tuscany thesanetravel.com 1460145161montepulciano tuscany thesanetravel.com 1460153162montepulciano tuscany thesanetravel.com 1460264163montepulciano tuscany thesanetravel.com 1460184164montepulciano tuscany thesanetravel.com 1460194165montepulciano tuscany thesanetravel.com 1460179166montepulciano tuscany thesanetravel.com 1460214The sanctuary of the Madonna di San Biagio is within 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.168montepulciano tuscany thesanetravel.com 1460250169montepulciano tuscany thesanetravel.com 1460221When visiting this awesome part of Tuscany, take the opportunity to use the healing power of the thermal waters of Tuscany with a much deserved break at San Giovanni Terme Rapolano.

San Giovanni Terme Rapolano

Rediscover the pleasures for your senses by 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.171sangiovani remerapolano tuscany thesanetravel.com 154158172sangiovani remerapolano tuscany thesanetravel.com 145757173sangiovani remerapolano tuscany thesanetravel.com 145937174sangiovani remerapolano tuscany thesanetravel.com 153435Had a great time? Need more inspiration? Read one of many books set in Italy and Tuscany! Just a few final remarks before moving on.

Where to stay in Tuscany?

When you travel by car and want to do a 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. You should also carefully think about your Italy packing list before you go.

Villa Casalecchi

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.150villa casalecchi tuscany thesanetravel.com 1450061152 villa casalecchi tuscany thesanetravel.com 1450066153 villa casalecchi tuscany thesanetravel.com 1450071154villa casalecchi tuscany thesanetravel.com 1450084I 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.

Hotel Corsignano

100hotel corsignano pienza thesanetravel.com 1460010101hotel corsignano pienza thesanetravel.com 1460017102hotel corsignano pienza thesanetravel.com 1460026It was a great hotel with really awesome views of 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!Dreaming to see the best towns in Tuscany, Italy?  Read my suggestions of 8 towns to include in your Tuscany road trip. The first region of Tuscany you enter going south from Florence is Chianti.  You will be following one of the most scenic roads in the area. Find picture perfect views of that landscape on your way. Continue your journey through UNESCO listed Val d'Orcia up to Montepulciano. #besttownsofTuscany #TuscanyItaly #visitTuscany #tuscanydestinations #travelphotography #travelblog

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.

  • Published by Anita on April 12, 2019
  • Author: Anita Sane

    Anita 03 18

    About the author
    Anita is a part-time traveller, passionate photographer and a retired career woman from Latvia, 
    travelling mostly solo for more than 15 years. She is a skilled travel planner who plans and executes her travels by herself. Anita wants to show you how to travel the world and open your mind to new experiences. Follow her on FacebookInstagramPinterestTwitter and Bloglovin.


    Thanks Anita for putting together such a wonderful collection of towns to visit. We will be sure to follow in your footsteps, especially to the hot springs.
    I confess to not being interested in visiting towns, but I am beguiled by the scenery in between. This looks good!
    So many pretty towns to explore! I've only been to the bigger more well-known places in Tuscany and would love to visit more.
    Would love to spend some time exploring Tuscany. It is beautiful! I briefly passed through it many years ago and would love to return.
    Oh my goodness this looks beautiful! Very well presented. I need to get myself to Italy as soon as possible! I love your blog btw! All the best x
    I love Tuscany. Such a pretty part of the world. Thanks for sharing those gorgeous photos and suggestions.
    I love this road trip itinerary. Tuscany is actually something that I have been thinkin about for a very long time. Only do it with a bike. I'm definitely saving this post for later, I love these Italien towns, it always looks so gorgeous!

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