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If you are planning a trip to Italy, visiting the rolling hills and the charming towns of Tuscan countryside is a must. While major cities like Rome or Venice are incredible, the real heart of Italy is in its smaller towns. After spending over a week in Tuscany and visiting almost every small town in Tuscany, I can tell you that these places are where the magic is.
I have explored everything from the narrow streets of tiny towns like Pienza, Volterra to wine tasting in Montalcino, Greve and the famous historic centers of Florence, Pisa and Siena. I spent my days driving through olive groves, stopping for wine tasting in medieval castles and staying in a beautiful agriturismo.
Whether you are looking for the best wine towns in Tuscany or a quiet medieval town that feels untouched by time, I have put together the ultimate list. These are the most beautiful towns that are worth a spot in your Italy itinerary.
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Grab my FREE ItinerariesThe Magic of the Tuscan Towns And Villages
There is a reason why the Tuscan countryside is one of the most popular destinations in Europe. It is not just about the spectacular views of rolling green hills and cypress trees; it is about the feeling of stepping back into the Middle Ages.
The magic of Tuscany lies in its ability to slow you down. One moment you are driving along a road lined with olive groves and the next you are walking through the stone gates of a tiny town that is a thousand years old.
These medieval villages and hill towns are where you can sit in a quiet main square with a glass of red wine, listen to the church bells and enjoy the best things in life i.e good food and beautiful views.
Best Towns Of Tuscany
Tuscany is one of the best destinations to visit in Europe and Italy. There are so many places to see and small towns to explore but I’ve listed the best towns of Tuscany you can’t miss.
| Category | Towns |
| Best Hill Towns | San Gimignano, Montepulciano, Montalcino, Cortona, Volterra |
| Best Small Towns | Pienza, San Quirico d’Orcia, Bolgheri, Monteriggioni |
| Best Cities | Florence, Siena, Lucca, Pisa, Livorno |
| Best Historic Villages | Pienza, Montalcino, Montepulciano, Bolgheri, Cortona |
Pienza
For me, Pienza is all about the senses and one of the best small towns to visit in Val d’Orcia. As soon as you step into the historic center, you are hit with the sharp, salty smell of pecorino cheese wafting from the storefronts.
It is a great place to grab a table for lunch and just indulge in a cheese tasting. I loved wandering through the medieval cobbled stone alleys. They have such a romantic vibe, especially the ones with names like “Street of Love.”
The real highlight and a must do is walking along the town walls. The sweeping views of the val d’orcia and cypress trees are breathtaking. It is easily one of the nicest towns in tuscany to just slow down and breathe.
San Quirico d’Orcia
San Quirico felt like a breath of fresh air because it is so quiet and very close to Pienza. While most people rush past it, I found it to be a great place to escape the crowds.
My favorite memory here was finding the Horti Leonini gardens. I spent a long time walking through those manicured 13th century hedges; it felt like having a private garden all to myself.
It is a medieval town that feels authentic and lived-in. If you are on a road trip in Tuscany, do not skip this tiny town.
Montalcino
You cannot visit Tuscany and not stop here – it is the wine capital of Tuscany. As a sommelier, visiting the home of Brunello di Montalcino was a huge bucket list moment for me. The town is rugged and sits high on a hill, dominated by a massive 14th century fortezza.
I highly recommend heading straight to the Fortezza for the sweeping views of the valley. Standing on those ramparts, looking out over the province of siena, you truly realize why this is one of the most beautiful towns in Italy.
It is the perfect place to grab a glass of red wine at the wine bar inside the fort and just take it all in.
Montepulciano
This is easily one of my favorite Tuscan towns. There is something so satisfying about the steep climb up the main street toward the piazza grande. It is the perfect place to stroll, pop into enotecas for a quick wine tasting and then find a spot for a long lunch.
The Vino Nobile di Montepulciano is exceptional, and I spent a lot of time chatting with locals in the wine shops. Even with the Twilight movie fame, the town feels grounded in its medieval architecture.
Watching the sun set over the surrounding countryside from one of the viewpoints was a highlight of my trip. Montepulciano is one of the best places to stay in Val d’orcia.
Cortona
Cortona feels like a movie set but in the best way possible. Perched high on a hill, the spectacular views from the town are endless. I loved getting lost in the medieval streets that lead away from the Piazza della Repubblica.
It is a great place to browse for treasures in the antique shops. Even though it is famous from Under the Tuscan Sun movie, it still feels like a beautiful small town where you can find a quiet corner.
You must visit the Piazza Signorelli and the MAEC (Etruscan Academy Museum) to see some of the rich history of the area. I spent my time wandering the narrow streets and finding hidden medieval buildings that most tourists walk right past.
It is the perfect place to stop for a day trip from Siena and soak in the Tuscan sun.
Arezzo
Arezzo surprised me with how grand it feels. The Piazza Grande is one of the most unique squares I have seen with its sloping pavement and beautiful medieval buildings.
It is a best city for those who want a mix of history and a local, non-touristy vibe. You must visit the historic center and the Basilica of San Francesco to see the famous frescoes.
It feels like a real, working city with deep roots in the Middle Ages. I loved exploring the antique shops that line the main street. If you are looking for a best city that is off the beaten track, Arezzo is one of the best towns in Tuscany to add to your next trip.
Volterra
If you want a town that feels ancient and a bit mysterious, Volterra is the place. It sits on a rocky outcrop and has a much moodier vibe than the sun-drenched towns of the Val d’Orcia. I was fascinated by the Etruscan times history here – you can actually see the old city walls from that era.
The historic center is home to a stunning Roman Theatre and the Palazzo dei Priori on the main square. Walking through the narrow streets lined with alabaster shops felt like stepping back into a different version of the Tuscan countryside.
Lucca
Lucca is one of the nicest towns in Tuscany because it is so easy to love. My favorite experience here was renting a bike and riding along the top of the medieval walls that completely encircle the historic center. Lucca is the best city if you want a break from the steep hills.
You cannot miss the Piazza dell’Anfiteatro, which was built on the site of an old Roman arena. It is the perfect place to sit with a drink and people-watch.
I also recommend climbing the Guinigi Tower for the best view of the red-tiled roofs. The Gothic architecture of the Lucca Cathedral is another must-see highlight during your visit.
San Gimignano
If you want to experience what a medieval hilltop town looked like in its prime, you have to visit San Gimignano. I arrived during the golden hour, and seeing the silhouette of the 14 remaining towers against the Tuscan sun was a highlight of my road trip.
It is famously called the “Manhattan of the Middle Ages”, and walking through the city walls feels like stepping back into the 13th century. San Gimignano is one of the most popular day trips from Florence.
I loved wandering the narrow streets and popping into the boutique shops to taste truffles. Visit the Piazza della Cisterna, which is the most beautiful main square in the village.
If you would like to go wine tasting somewhere close to Siena, San Gimignano is the perfect spot. As a sommelier, I highly recommend stopping for a glass of Vernaccia di San Gimignano, the local white wine, at one of the enotecas (wine bars).
Greve in Chianti
Greve is the gateway to the Chianti wine region, and it has a relaxed, market-town vibe. I spent a lovely morning in the Piazza Matteotti, which is a unique triangular main square surrounded by arched porticos.
It is a great place to find good food and local crafts before heading to the best wineries of Chianti in Tuscany.
The highlight for any wine lover is the Antica Macelleria Falorni, a famous butcher shop and wine cellar where you can taste incredible meats and red wine. I also recommend exploring the surrounding countryside filled with vineyards and olive groves.
If you are looking for a best wine town that feels authentic and less “touristy” than the hilltop villages, Greve is the perfect place.
Radda in Chianti
Radda is another Medieval town that sits right in the heart of the Chianti wine region. I loved the stone buildings and the way the town walls still encircle the historic center. It feels very rugged and ancient compared to the softer landscapes of the Val d’Orcia.
Make sure to visit the Propositura di San Niccolò to see the medieval buildings and then find a local tavern for a wine tasting. The views of the Tuscan countryside from the edge of the town are simply spectacular.
Monteriggioni
Monteriggioni is a tiny town, but it is one of the most iconic sights in Central Italy. You can see the perfectly circular medieval walls and towers from the highway long before you arrive. It is a great stop between Siena and San Gimignano.
There is only one main square, the Piazza Roma and a few narrow streets, but the history here is incredible. I recommend paying the small fee to walk along the top of the city walls for a best views of the town and the surrounding countryside.
Siena
Siena is my personal favorite city in Tuscany. Standing in the Piazza del Campo, the shell-shaped main square, for the first time is a “wow” moment. This is where the famous horse race (Palio) takes place and the history is palpable in every brick.
I actually prefer the Siena Cathedral (Duomo di Siena) over the one in Florence because of its intricate Gothic architecture and incredible floor mosaics.
Climbing the Torre del Mangia is a must for the best views of the city. Siena is the ideal base if you want to explore the Chianti wine region and the towns and villages of Val d’Orcia.
Bolgheri
Bolgheri is a dream for any wine lover. The drive into town is one of the most iconic experiences in Italy, thanks to the Viale dei Cipressi, a straight road lined with over 2,000 cypress trees.
Bolgheri is fascinating because it is the birthplace of the “Super Tuscans”. Wineries here broke away from traditional rules to create unique blends and world famous wines.
The town itself is small with a charming medieval castle at the entrance. Although it is small, Bolgheri is much more upscale and polished than the rustic villages of the Val d’Orcia.
You must walk the narrow streets and stop for a wine tasting of a bold red wine. It is a great town to enjoy a long lunch paired with some of the best wines in Tuscany before heading toward the Tyrrhenian Sea.
Livorno
Livorno is a hidden gem that is often overlooked by travelers rushing to the hill towns but this port city has a unique character.
It is a best city for seafood lovers and those who want to see a different side of Central Italy. My favorite area is “Venezia Nuova”, a district filled with canals and medieval buildings that remind me of Venice.
The Terrazza Mascagni, a massive checkerboard waterfront terrace, is a highlight for spectacular views of the sea. I enjoyed wandering through the Mercato Centrale, one of the largest food markets in Europe.
Livorno is amazing to see local life and taste the famous Cacciucco (fish stew). If you want a break from the standard Tuscan countryside vibe, Livorno is worth visiting.
Pisa
Most people only go to Pisa to visit the most popular attraction – the Leaning Tower of Pisa, but there is more to this than just a photo op. Of course, you have to visit the Piazza dei Miracoli to see the Leaning Tower, the Baptistery, and the Pisa Cathedral. The Gothic architecture and the white marble against the green grass is truly a sight to behold.
Beyond the tower, I enjoyed walking along the Arno River and exploring the historic center. The Piazza dei Cavalieri is another must-see main square with an incredible rich history. It is an easy day trip by public transportation from Florence.
While it can be super crowded in high season, the architectural scale of the monuments makes it a great place for any history buff.
Florence
Florence is the soul of the Renaissance and one of the best cities in Italy that everyone needs to visit at least once. I have spent a lot of time here and the energy is unmatched. You would need atleast 3 days in Florence and cannot miss the most famous Duomo (Cathedral of Santa Maria del Fiore) or the Palazzo Vecchio in the Piazza della Signoria.
As someone who visited Florence multiple times, I recommend crossing the Ponte Vecchio and heading to the Oltrarno side for a more local feel. If you are into shopping, I recommend gold shopping and engraved leather goods in Florence. I still use my gold pendant and earrings I bought from Florence to this day.
Whether you are here for the Renaissance art at the Uffizi or just to stroll the medieval streets, Florence is an incredible city to start or end your Italy trip itinerary.
FAQs About Visiting The Best Towns Of Tuscany
How many days do you need to visit the best towns in Tuscany?
To truly appreciate the Tuscan countryside and explore the best towns in Tuscany without feeling rushed, I recommend at least five to seven days.
An Italian trip itinerary with a full week in Tuscany gives you enough time to use a central base like Siena and take a day trip to various hill towns and wine regions.
If you only have a few days in the Tuscan countryside, focus on just two or three smaller towns like San Gimignano, Montepulciano and the towns of Val d’Orcia so you can soak in the medieval architecture and enjoy the good food.
Do you need a car to explore the Tuscan countryside?
While public transportation connects major cities like Florence, Pisa and Siena, renting a car is the best way to truly explore the Tuscan countryside.
Having your own vehicle allows you to get off the beaten path and visit smaller towns like Pienza and Montalcino which are harder to reach by train or bus.
A road trip gives you the freedom to pull over for a spontaneous wine tasting or to capture the best view of the cypress trees lining the hills.
If you can’t rent a car, you can choose to take a guided tour from Florence or Siena. These are some fo the best guided tours from Florence and Siena.
Best Guided Wine Tours From Florence And Siena
What is the best town to base yourself in for a Tuscany road trip?
For the best Tuscany road trip experience, Siena is the perfect city to base yourself. It is centrally located, making it easy to reach the Chianti wine region to the north and the Val d’Orcia to the south.
Staying in Siena allows you to experience the rich history and Gothic architecture of Siena in the evenings, while taking day trips to the beautiful villages and historic churches of the surrounding region.
When is the best time to visit the small towns in Tuscany?
The ideal time to visit is during the shoulder seasons of May to June and September to October.
During the shoulder months, the weather is beautiful, the vineyards and olive groves are vibrant and the historic center of each town is less congested than in the high season of July and August.
We visited in the third week of May and had the best time. We saw so many wild poppies. And you will have a much more relaxed experience enjoying a red wine in the main square without battling huge crowds.
Which Tuscan towns are the absolute best for wine tasting?
Tuscany is a haven for wine connoisseurs. As a sommelier and wine lover, I always recommend wine enthusiasts to visit Montalcino, Montepulciano and Greve in Chianti.
Montalcino is home to the famous Brunello di Montalcino – the wine of Tuscany. Montalcino has some of the best wineries in Tuscany and is only an hour away from Siena.
Montepulciano has incredible underground wine cellars where you can taste the famous Vino Nobile di Montepulciano.
If you prefer a white wine, head to San Gimignano for a glass of Vernaccia di San Gimignano while enjoying the spectacular views.
For classic Tuscan wines, visit Greve in Chianti. If you are exploring Pisa, check out the wineries of Bolgheri.
What are the best cities in Tuscany?
The best cities in Tuscany are hands down Florence, Siena and Lucca.
Florence is the art capital and known for its Renaissance art and historical significance, while Siena is smaller and intimate with medieval architecture.
Lucca is a fantastic, flat-walled city that is perfect for families.
I visited Florence, Siena and Lucca and loved all of them. But personally, I have a special soft spot for Siena as it is close to the wine country and several smaller medieval villages of Tuscany.
What are the prettiest towns in Tuscany?
Uff, where do I start? There is beauty in every corner of Tuscany and it is really hard to select a few towns as all of them are equally beautiful.
Some of the most beautiful towns that must be part of your Tuscany itinerary are Pienza, Montepulciano, Volterra and San Gimignano.
Pienza is a UNESCO World Heritage Site with incredibly romantic narrow streets overlooking the Val d’Orcia.
San Gimignano is striking with its towering medieval buildings that create a unique skyline, while Montepulciano offers steep medieval streets lined with enotecas and trattorias.
What are some recommended places to visit in Tuscany besides Florence?
If you want to explore beyond Florence, I highly recommend visiting Siena (my favorite city in Central Tuscany) and San Gimignano on the way.
Volterra is a great town to visit and known for its Etruscan times history. Arezzo is another fantastic town that boasts a beautiful sloping main square and fewer crowds.
For a small town experience, heading down to the Val d’Orcia and see Pienza, Montepulciano and San Quirico d’Orcia is an absolute must.
What are some less crowded and quieter vacation spots in Tuscany, Italy?
For a quieter vacation off the beaten track, look toward smaller towns like San Quirico d’Orcia, Monteriggioni or even the coastal wine town of Bolgheri.
San Quirico is so peaceful and surrounded by many agriturismos. Monteriggioni is a small town that many people miss and is perfect for a quieter vacation.
Final Thoughts
I have been to Italy several times and many regions and cities like Rome, Venice, Amalfi Coast, Lake Como, Portofino and many more. And after spending over a week exploring the Tuscan countryside, I can confidently say that this region will steal your heart and small towns are where the charm lies.
Whether you are driving past perfectly lined cypress trees or sipping red wine in a quiet medieval town, the experience is simply unmatched.
If I had to narrow down my absolute favorites, the best wine towns of Montalcino and Montepulciano are right at the top of my list. As a sommelier, the wine tasting experiences there are incredible and the medieval architecture is stunning.
The beautiful small towns of the Val d’Orcia like Pienza and San Quirico d’Orcia and the towns around Siena like San Gimignano and Volterra are also perfect to enjoy the spectacular views.
If you are planning your next trip and need a bigger base, Siena is amazing. It gives you that grand historic center feel while keeping you close enough for a quick day trip to the smaller villages. For the most stunning renaissance art, visit Florence.
Whatever you choose, rent a car, book a beautiful agriturismo and take your time exploring the best towns in Tuscany. It is a trip you will never forget!
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