Are you dreaming of the rolling hills of Tuscany? If this iconic Italian region is calling your name, we need to chat. I’ve recently returned from leading a small group, multiday tour in the region and have fallen head over heels in love again! There are so many beautiful Tuscany towns to visit, that you really can’t go wrong. That said, each one offers different views and attractions so it pays to do a little research whilst planning your travels. Keep reading to find out about my favorite Tuscany medieval towns to visit in 2024 and beyond!
Why visit Tuscany Medieval Towns in 2024?
Tuscany is a region that has something to offer everyone. Whether you are a history buff, a foodie, or a nature lover, Tuscany has it all. The medieval towns in Tuscany are some of the most well-preserved in the world, and they offer visitors a chance to step back in time and experience the rich history and culture of the region.
If you have been dreaming of your own version of Under the Tuscan Sun for years, there’s no better time to visit especially after the last few years of pandemic life. Book the plane ticket!
Want to visit medieval towns in Tuscany with me? Join our Untold Italy week long adventure to the region in Spring or Fall. We’ll show you the highlights of Tuscany getting you off the beaten track and experiencing the region like a local. On this 8 day tour we’ll visit beautiful hilltop towns, and meet wonderful locals for a truly once-in-a-lifetime experience. Of course, we’ll also wine and dine our way around this gorgeous region while enjoying unforgettable experiences together. Find out more now.
The Top 8 Tuscany Medieval Towns to Visit
1. Montefioralle
There are about 40 residents left in this picturebook perfect Tuscan town, so there’s obviously not a ton to do. But that’s not why you’re here! It’s quite possibly one of the most picturesque hamlets I’ve ever seen – think cobblestones, wisteria, flower pots, cute Italian cats, and sweeping views over the rolling hills. You don’t need long here – between 30 minutes to an hour.
2. Monteriggioni
This is probably the most medieval Tuscan town you could ever visit! It’s literally a fortified hamlet with the medieval walls and towers still intact. On our Untold Italy tour this year, we organised a very special surprise for our guests with locals dressed up in medieval costumes and it was the icing on the cake to our visit here. There are some cute shops in town like a jeweller and a few clothing stores too, as well as a few bars for refreshments.
3. Pienza
Pienza is a small town located in the Val d’Orcia, which is in the Southern part of Tuscany. It’s one of my favorite places because it’s famous for pecorino cheese! It is so picturesque thanks to Pope Pius II, who had the entire town rebuilt to embody an ‘ideal town’! Expect street names like ‘love street’ and more, plus of course oustanding views of the surrounding countryside. Don’t miss pecorino tasting and look out for the famous aglione garlic here – it’s native to this area. One of the must-visit attractions in Pienza is the Palazzo Piccolomini, which was built in the 15th century.
4. Lucca
Every visit to this cute Tuscan town, I stop and think ‘I could live here’. There’s something that just feels so village-like and liveable here and I love that everyone bikes around town. Encircled by medieval walls, the ‘thing’ to do in Lucca is bike-ride around them which is what we did during one of my visits with the Tuscan Tourist Board in 2022. If you like antiques, Lucca is the place to be too – it takes place every third weekend of the month!
5. San Gimignano
Perhaps the most famous medieval Tuscan town of them all, San Gimignano is often described as a ‘medieval Manhattan’ thanks to its still-standing towers. The tour buses have long discovered this quaint village, but that doesn’t make me love it any less. Be sure to climb the remaining tower for a wonderful view, and otherwise just enjoy wandering the streets and soaking in its small town vibes. The best time to visit is before the tour buses arrive at 10am.
6. Siena
I absolutely adore Siena and its medieval traditions that are carried on to this day. Most notably, the Palio horse race which takes place twice a year in the summertime! One of my favorite things to do in Siena is arrange a walking tour with a guide to learn more about its rich history (they were constantly at war with Siena) and also for the chance to visit a contrada (neighborhood). Siena definitely deserves a few days of discovery time.
7. Florence
It hardly needs an introduction, but this guide would be remiss not to include beautiful Florence. Art lovers will have an absolute ball here at the Uffizi and Accademia Galleries, whilst perfume enthusiasts will adore a trip to the Farmaceutica di Santa Maria Novella perfume shop.
Foodies this is your place too and you can’t not try the infamous Lampredotto street food (the fourth stomach of a cow in a panino!) There is really so much to do in Florence but do understand that it’s extremely busy with tourists most times of the year now.
8. San Miniato
I first visited this gorgeous, somewhat off-the-beaten path town in 2019. I was a guest on Emiko Davies’ white truffle retreat and had the pleasure of visiting town during their white truffle festival (aka heaven). This town has undoubtedly remained one of my favorites thanks to all its delicious food, so it’s well worth the trip for dedicated foodies.
It’s located on a hilltop in central Tuscany and known for its beautiful churches and palaces. One of the must-visit attractions in San Miniato is the 11th-century Rocca di Federico II, which offers stunning views of the surrounding countryside. Try to time your visit during the truffle festival, which takes place in November.
Other Must-Visit Tuscany Medieval Towns
In addition to my favorite 8 Tuscany medieval towns, there are many other towns in the region that are worth a visit. Some of these include:
– Montalcino
Montalcino is a town located in the province of Siena in Tuscany. It is known for its beautiful views and its famous Brunello di Montalcino wine. One of the must-visit attractions in Montalcino is the 14th-century fortress, which now houses the Museo Civico e Diocesano d’Arte Sacra. The town is also home to the annual “Festa del Brunello,” a wine festival that takes place in February.
– Arezzo
Arezzo Tuscany Italy is a town that is rich in history and culture. It is located in eastern Tuscany and is known for its beautiful churches and museums.
One of the must-visit attractions in Arezzo is the Basilica di San Francesco, which houses the famous fresco cycle “The Legend of the True Cross” by Piero della Francesca.
Arezzo is also home to the annual Giostra del Saracino, a medieval jousting tournament that takes place in June and September.
– Certaldo
Certaldo is a small town located in the province of Florence in Tuscany. It is known for its beautiful medieval architecture and is often referred to as the “city of Boccaccio,” as the writer lived here in the 14th century. One of the must-visit attractions in Certaldo is the Palazzo Pretorio, which houses the Museo Civico and contains works by local artists.
– Pisa
Famous for the Leaning Tower, Pisa is definitely worth popping in for a quick visit. It’s a university town so has a really fun, friendly atmosphere. It’s a very pretty city but probably not one of my favorites as it’s just so busy with visitors at the Leaning Tower. International travelers take note that the main airport in Tuscany is actually in Pisa and not Florence! Make the most of Pisa with this guided tour (including pickup from Florence) with Walks of Italy.
– Volterra
Another gorgeous Tuscan hilltop town, Volterra was more recently made famous thanks to Twilight. It’s famous for its alabaster artisans, so be sure to visit some workshops when you’re in town if you have an interest in crafts. It’s really fascinating watching how they work the alabaster which looks similar to marble!
– Castellina in Chianti
Castellina has a big medieval fortress right in the middle of the small town that’s really impressive to wander through! There are a few nice restaurants and shops to explore too.
Each of these towns has its own unique charm and history, and they are all worth exploring.
The Best Towns in Tuscany to Stay
When visiting Tuscany, it is important to choose the right accommodation for your needs. There are many options available, from budget-friendly hotels to luxurious villas. Some of the best towns in Tuscany to stay in include:
- Florence: Day trips into Chianti are easy from here
- Siena: Day trips into the Val d’Orcia are easy from here
- San Gimignano: Enjoy the town when all the tour buses leave in the evenings and early mornings. You can do daytrips around the countryside from here
- Lucca: A wonderful home base to feel like a local in Tuscany
- Montalcino: Wine lovers interested in exploring the Val d’Orcia should consider staying here
Each of these towns has its own unique charm and is a great base for exploring the surrounding area.
The Best 5-Star Tuscany Hotels for a Luxurious Stay
If you are looking for a luxurious stay in Tuscany, there are many 5-star hotels to choose from. Some of the best include:
- Castello di Casole: Situated in Casole d’Elsa, this is a stunning luxury hotel with a pool, spa and restaurants on-site. The grounds are absolutely stunning and this is a very special place to stay.
- Il Castelfalfi: A stunning borgo in the Tuscan countryside, there is a spa and restaurant on site here too.
- Borgo Santo Pietro: Another wonderfully gorgeous luxury hotel in the countryside with 5 hectares of private gardens, and a swimming pool. It’s about a 40 minute drive to Siena.
- Rosewood Castiglion del Bosco: This is my favorite for the location as it’s in the Val d’Orcia and very close to the town of Montalcino making it convenient for exploring the area. There is a swimming pool, Turkish bath, sauna, and wine tastings on site too.
Tuscany Hilltop Towns
One of the best ways to experience the beauty of Tuscany is by visiting its hilltop towns. These towns offer stunning views of the surrounding countryside and are a great place to relax and take in the scenery. Some of the best Tuscany hilltop towns to visit include:
- Montepulciano
- Cortona
- Montalcino
- San Gimignano
- Volterra
Exploring Tuscany Medieval Towns
When exploring Tuscany medieval towns, there are many things to do and see. Some of the top attractions include:
- Visiting the local museums and churches
- Go wine tasting in Chianti with a small group tour so you don’t need to worry about drinking and driving
- Trying the local cuisine, including Pecorino cheese, Chianti Classico wine/Brunello di Montalcino, Pici pasta with sugo or wild board
- Attending local festivals and events, such as the Palio di Siena or the jousting in Arezzo
- Exploring the surrounding countryside, including vineyards and olive groves
- Taking a hot air balloon ride for a bird’s eye view of the region
Not comfortable renting a car or perhaps you don’t have a lot of time to spare? Join a day tour from Florence to explore Tuscany’s top medieval towns with Walks of Italy, one of my favorite small tour companies. I love the sound of this one that picks you up from Florence and takes you to Chianti, Siena and San Gimignano.
How to Get to Tuscany and Around Tuscany Medieval Towns
Tuscany is easily accessible from all main cities in Italy. The region has several airports, including Florence Airport and Pisa Airport, however Pisa is the main international airport. There are also several train stations throughout the region, so you can easily travel from Milan or Rome to Florence on train and pickup a car from there. Once you arrive in Tuscany, the best way to explore the medieval towns is by car. Public transport is unreliable or non-existant in some places. This will give you the flexibility to visit the towns at your own pace and take in the beautiful scenery.
Want to visit medieval towns in Tuscany with me? Join our Untold Italy week long adventure to the region in Spring or Fall. We’ll show you the highlights of Tuscany getting you off the beaten track and experiencing the region like a local. On this 8 day tour we’ll visit beautiful hilltop towns, and meet wonderful locals for a truly once-in-a-lifetime experience. Of course, we’ll also wine and dine our way around this gorgeous region while enjoying unforgettable experiences together. Find out more now.
Visit medieval towns in Tuscany in 2024
Tuscany is a region that is rich in history, culture, and natural beauty. Its medieval towns offer visitors a chance to step back in time and experience the region’s rich history and culture. Whether you are a history buff, a foodie, or a nature lover, Tuscany has something to offer everyone. So, why not plan a visit to Tuscany medieval towns in 2023 and experience the region’s beauty for yourself? Looking for more information about Tuscany? Have a read of my guide to the Chianti region.