Tuscany has a way of pulling me back. Having visited twice, I’ve learned that the best Tuscan towns aren’t just the famous ones—you have to slow down and look beyond the postcards.
In the province of Siena, time moves differently. Mornings begin with a quiet espresso in a medieval piazza, afternoons are for meandering through vineyards, and evenings bring conversations over a simple but perfect meal.
Whether you love history, food, or just the beauty of an unhurried day, these towns offer a glimpse into Tuscany’s soul.
If you’re planning a trip and wondering where to go, here’s my list of towns in the province of Siena, and a tiny portion of Arezzo in Tuscany that are truly worth a visit.
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Best Tuscan Towns to Visit
Tuscany, in central Italy, is made up of ten provinces, including Siena. Known for its rolling vineyards, historic towns, and curvy roads, it’s considered the birthplace of the Italian Renaissance. The region’s diverse landscapes, from coastal beaches to olive-covered hills, make it one of Italy’s most picturesque and culturally rich destinations.
From A to Z here are the towns in Tuscany worthy of a visit.
1. Arezzo is a treasure hunter’s delight
Arezzo is an ancient Etruscan city that is older than Alexandria in Egypt making it one of the top towns to visit in Tuscany.
Mostly developed in the 9th century, wandering the historic centre and admiring the medieval details, the balconies, lanterns, courtyards and all of its lovely alleyways, is my favourite thing to do here.
Arezzo is so charming it served as the backdrop to one of my favourite movies Life is Beautiful. When I found that out, I knew I needed to visit here!
My recommended tips for visiting Arezzo:
- Shop! This town is known for its monthly antique market, on the first weekend of every month
- Explore the old historic centre, with notable landmarks of San Francesco Basilica (seen in the movie The English Patient), and the stained glass windows of the Cathedral of San Donato
- Try my favourites, restaurants Caffe Vasari or Chiave D’Oro, and discover more recommended places to stay and eat here
- Market day is on Saturday
2. Cortona is made for strolling
Cortona looks and feels a bit different than the other towns in Tuscany.
This hilltop is an elegant stone-clad town from the 13th century with a larger and busier piazza and an endless amount of winding streets chock-full of dreamy places to stay.
If you are a fan of Under the Tuscan Sun, first, the book then the movie you’ll know the town of Cortona was where it all started. That was my reason for going here and so glad I did, without a doubt, this is one of the best towns to visit in Tuscany.
My recommended tips for visiting Cortona:
- Admire the Etruscan wall, the noteworthy Church of San Francesco and the Museo dell’Accademia Etrusca
- Shop for local artisanal products like ceramics, leather goods, and wine
- I ate at La Buccaccia, Osteria del Teatro and Enoteca Molesini
- Market day is Saturday
3. Lucignano is known as the Pearl of the Val di Chiana
Lucignano is an under-the-radar hilltop town overlooking the beautiful Val di Chiana.
As one of the best-kept secrets of towns to visit in Tuscany, Lucignano receives very few tourists.
It’s one of those must-see Tuscany towns to visit if you love nothing more than an authentic experience. That’s why I went here.
My recommended tips for visiting Lucignano:
- Grab an ice cream at Gelateria Snoopy and wander the town
- Admire the scenic views of the beautiful countryside
- I ate at Zenzero, and think you should too
- Market day is Thursday
4. Montalcino is famous for its wine
Montalcino is one of those beautiful villages near Siena that is worth visiting. With its hilltop views and a medieval town centre full of well-preserved buildings dating back to the 13th century.
This Tuscan village is famous for its delicious Brunello di Montalcino wine produced using grapes from the surrounding vineyards.
My recommended tips for visiting Montalcino:
- Do a wine-tasting in the fortress of Montalcino where you can sample most of the nearby producers at once, it’s an unbelievable experience you won’t want to miss
- Explore the historic centre including the church of Sant’Agostino
- Market day is Friday
5. Montefollonico is off the beaten path
This under-the-radar village is passed by most tourists en route to Pienza. But don’t.
If you want to see what a peaceful village life might be like, take a detour and go here. The pretty narrow streets in Montefollonico are impressive.
Red and yellow brick, shuttered windows and flower-filled iron balconies, this is a tranquil way of life.
My recommended tips for visiting Montefollonico:
- Get lost in the tiny streets
- Explore the fortified defence wall from the 6th century, the Romanesque church of San Leonardo, and the church of San Bartolomeo from the 12th century
- I ate at La Botte Piena and it was delicious of course
- Market day is Tuesday afternoons
6. Montepulciano is for wine lovers
Montepulciano is one of Tuscany’s prettiest towns and with its wine culture, it easily tops my list of worthy places. It’s also one of the best Tuscany towns to stay in.
The walls surrounding this medieval town date back to the 14th century, and the views are sublime.
Wine enthusiasts will love sampling the latest vintage of Brunello wines in the cozy wine-tasting cellars.
My recommended tips for visiting Montepulciano:
- Admire the main square made of Travertine and the Duomo
- Sip on some wine in a cozy wine-tasting cellar like La Gatta Vecchia (my fave)
- I ate at Osteria l’Aquachetta and La Grotta and they were the highlights of my trip
- Market day is Thursday
7. Monteriggioni is known as the stone crown
This hilltop village can be seen from afar. The stone wall that encircles the town resembles a stone crown. It’s one of those small towns near Siena Italy that can easily be added to your itinerary.
Monteriggioni is considered one of the oldest towns in Italy. Records show that it has been inhabited since the 8th century. History buffs, this is one of the best towns in Tuscany to add to your list.
My recommended tips for visiting Monteriggioni:
- Tour the Monteriggioni castle, founded in 1220
- Admire the views from the 14 towers found within the fortified wall
8. Monticchiello is known for its theatre
Monticcheillo is a hidden gem in Tuscany.
This small authentic village dates back to Etruscan and Roman times as a former crossroads connecting other nearby cities. You can still see the medieval wall and fortress protecting the city from afar.
My recommended tips for visiting Monticchiello:
- Attend the annual Teatro Povero di Monticchiello, a unique outdoor theatre festival in August
- Explore the castle and walls of Monticchiello and admire the scenic views
- Relax at the nearby thermal baths of Bagno Vignoni
- The restaurant that caught my was La Porta, but I didn’t eat there
9. Pienza is famous for its pecorino cheese
The hilltop town of Pienza is a well-preserved UNESCO-designated Renaissance town that has been virtually untouched since the 15th century.
As one of the most beautiful towns in Tuscany, the biggest draw is the scenic views of the Val d’Orcia countryside and the Pecorino di Pienza cheese.
My recommended tips for visiting Pienza:
- Stroll the incredibly romantic streets with names Via dell’Amore (or Love Street) and Via del Bacio (or Kiss Street)
- Visit the main square with the important landmarks of the three Palazzo and the Cathedral
- I ate at the delicious La Bandita Town House Caffe
- Market day is Friday
10. Radda is famous for its Chianti wines
Radda is a charming medieval town in the heart of Chianti, surrounded by rolling vineyards and stone-paved streets that feel untouched by time.
It’s worth visiting for its renowned wine culture, scenic countryside views, and the opportunity to experience an authentic, slower-paced Tuscan village.
My recommended tips for visiting Radda:
- Wander through the medieval streets, visit the 15th-century Palazzo del Podestà, and soak in the panoramic views of the Chianti countryside
- Stop by a nearby vineyard like Castello di Radda or Volpaia for a tasting of Chianti Classico and a glimpse into traditional winemaking
- Market day is on the fourth Monday of every month in the early afternoon into the evening
11. San Gimignano is known for its towers
San Gimignano is one of the most beautiful towns in Tuscany, and the most recognizable.
This UNESCO-designated hilltop town is famous for its towers that can be seen off in the distance. Dubbed the ‘Medieval Manhattan’ 13 of the 65 towers survive today making it one of the best towns near Siena Italy.
My recommended tips for visiting San Gimignano:
- Visit the 15th-century Cathedral, considered one of the best in Tuscany
- Climb the Torre Grosse, the tallest tower in San Gimignano, built in 1311
- Wander the Palazzo Comunale, home to a museum and art gallery
- Market day is Thursday and Saturday
12. San Quirico D’Orcia is famous for not being famous
One of the best towns to visit is one that no one knows about.
San Quirico has one of the most beautiful countryside and the drive to visit this town is worth it. The historic centre is authentic and beautiful and you won’t find a tourist in sight.
My recommended tips for visiting San Quirico:
- Get your cameras ready, as the scenic drive to the San Quirico area is sublime
- Beautiful garden in the centre of town
- Market day is the 1st and 4th Tuesday of every month
13. Siena is known for its impressive historic sites
Siena is a large medieval Tuscan city that can’t be missed. As far as cities in Tuscany to visit, this is by far one of the most popular.
The impressive historic city centre has many streets to simply get lost in. Admiring the well-preserved architecture makes you feel like you are stepping back in time, to 1300.
While the other best Tuscany towns that appear on this list can be experienced in an hour or two, Siena needs a full day to be explored, if not more.
My recommended tips for visiting Siena:
- Visit the Piazza del Campo, considered to be one of Europe’s greatest medieval squares
- Climb the Torre del Mangia, the oldest and tallest tower in Italy
- Admire Italy’s most important religious buildings, the Siena Cathedral
- Watch the Palio di Siena festival, the world-famous horse race played out in the piazza in July and August
- Market day is Wednesday
14. Torrita di Siena is for history lovers
Torrita di Siena, not to be confused with the much larger city of Siena, is a charming sleepy village to visit while in the Siena area.
The origins date back to the Etruscan and Roman periods, and the historic centre makes you feel like you’ve stepped back in time as you access it through four medieval gates.
My recommended tips for visiting Torrita di Siena:
- Visit the medieval Torrita Castle from the 13th-century castle which also offers panoramic views of the surrounding countryside
- The many churches, most notable being the Romanesque church of Sante Flora and Lucilla
- Market day is every Friday
Where I Stayed to Explore These Tuscan Towns
During my stay at Siena House, a beautifully restored villa, I found the perfect balance of authentic Tuscan charm and modern comfort.
Every window framed sweeping views of distant hilltop villages, making even the simplest moments feel special.
With just four spacious suites, the villa offers an intimate retreat, complete with private living areas, a mezzanine, an outdoor kitchen, and a pool for lazy afternoons under the Tuscan sun.
The hosts, Malvin and Amanda, go above and beyond to make every guest feel at home, from their warm hospitality to the unforgettable homemade breakfasts that start each day on the perfect note.
Final Thoughts
As far as destinations go, Tuscany is perfect!
If you’re planning your own Tuscan adventure, check out my other articles for detailed itineraries to guide your travels through this beautiful part of Italy.
- Spending two days in Tuscany
- What to do for three days in Tuscany
- A four-day Tuscan itinerary
- How to spend five days in Tuscany
- An ideal week in Tuscany
