If you’re searching for the best Tuscan towns, the real question isn’t which ones are beautiful — they all are. It’s which ones are worth your time.
Some are polished and crowded. Others are quieter, slower, and far more memorable.
After returning to Tuscany more than once, I’ve learned the towns you remember aren’t always the famous ones — they’re the ones that match how you want to travel.
This list brings together both: the iconic and the under-the-radar, so you can choose the towns that will actually shape your experience.
This post may contain affiliate links, meaning I get a commission if you decide to purchase something through the links, at no additional cost to you. Read my Affiliate Disclosure.
How to Choose the Right Tuscan Town (Based on Your Travel Style)
Choosing the best hilltop towns isn’t about finding the most beautiful — they all are. It’s about choosing the ones that match how you want to experience Tuscany.
Some towns are lively and well-known. Others are quieter, where very little seems to change from one hour to the next.
If you’re not sure where to start, this is how I would choose.
| Travel Style | Towns to Visit |
|---|---|
| First-time visit | San Gimignano, Siena — iconic, historic, and instantly recognizable |
| Quiet, slow travel | Lucignano, Monticchiello — smaller, peaceful, and far less visited |
| Wine lovers | Montalcino, Montepulciano — known for Brunello wines and vineyard settings |
| Under-the-radar | San Quirico d’Orcia, Montefollonico — scenic, overlooked, and uncrowded |
| A good base to explore | Montepulciano, Cortona, Arezzo — well-located with good amenities |
The Mistake Most People Make When Visiting Towns in Tuscany
Most people try to see too many.
They build an itinerary around a checklist — ticking off as many towns as possible in a day — and end up experiencing none of them properly.
The reality is, many of these towns look similar at first glance: stone streets, hilltop views, a central piazza.
What makes them memorable isn’t how many you see. It’s how long you stay.
It’s a quiet morning before the shops open.
The long lunch that stretches into the afternoon.
The moment the day slows down, and you stop moving with it.
If I could suggest one thing, it would be this: choose fewer towns, and give them more time. You don’t want to return home, and each of the towns you visited becomes a blur. The goal is to make them each stand out.
Best Tuscan Towns to Visit
From A to Z, here are the towns I think are worth building into your Tuscany itinerary.
1. Arezzo is a treasure hunter’s delight
Arezzo feels lived-in in a way some towns in Tuscany don’t — less polished, more local, where daily life quietly unfolds around you.
Unlike the more curated hill towns, Arezzo has a slightly rougher edge, with fewer crowds and a stronger sense of everyday life. It’s a place where you’re not just visiting Tuscany — you’re observing it.
Go here if you want a Tuscan town that feels real, not staged.
My personal recommendations:
- 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 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 feels elevated — both in its setting and its energy — with a sense of quiet elegance that lingers as you wander.
There’s a refinement here that sets it apart, from its wide piazzas to its curated shops and sweeping views over the valley below.
Go here if you want something romantic, polished, and easy to settle into.
My personal recommendations:
- Admire the views from the Etruscan wall
- Shop for local artisanal products like ceramics and leather goods
- 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 feels like a town you weren’t meant to find — quiet, circular, and almost too still for Tuscany.
Its rare concentric layout makes it feel enclosed and self-contained, and with so few visitors, the silence becomes part of the experience.
Go here if you want to feel like you have Tuscany to yourself.
My personal recommendations:
- Grab an ice cream at Gelateria Snoopy and wander the town
- Admire the scenic views of the beautiful countryside
- I ate at Zenzero, and I think you should too
- Market day is Thursday
4. Montalcino is famous for its wine
Montalcino feels intentional — a place shaped as much by its wine as by its history.
Everything here seems to revolve around Brunello, from the surrounding vineyards to the understated rhythm of the town itself.
Go here if your trip to Tuscany is centred around wine.
My personal recommendations:
- 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
Montefollonico feels like a pause — the kind of place you almost miss, and then wonder why you don’t hear more about it.
It’s small, quiet, and largely untouched, with just enough detail in its streets and views to hold your attention.
Go here if you want stillness and a slower pace.
My personal recommendations:
- 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 feels cinematic — grand, vertical, and made for lingering over a glass of wine as the light shifts across the hills.
Compared to nearby towns, it’s more dramatic and atmospheric, with deeper wine cellars and sweeping views that unfold as you climb.
Go here if you want wine, views, and a bit of atmosphere.
My personal recommendations:
- Admire the main square made of Travertine and the Duomo, and stroll the streets
- 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
Monteriggioni feels contained — a perfectly enclosed medieval world that reveals itself all at once.
Its compact size and intact walls make it one of the easiest towns to take in quickly, but the visual impact is immediate.
Go here if you want something small, historic, and visually striking.
My personal recommendations:
- 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
Monticchiello feels thoughtful — a place where culture and community quietly shape the experience.
It’s less about sights and more about atmosphere, with its theatre tradition adding a layer you won’t find in other towns.
Go here if you’re drawn to places with a deeper cultural identity.
My personal recommendations:
- 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 eye was La Porta, but I didn’t eat there
9. Pienza is famous for its pecorino cheese
Pienza feels designed — balanced, harmonious, and almost too perfect in its proportions.
As a Renaissance “ideal city,” everything here is intentional, from its layout to its views over the Val d’Orcia.
Go here if you want a postcard of Tuscany at its most refined.
My personal recommendations:
- 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 Palazzi and the Cathedral
- I ate at the delicious La Bandita Town House Caffe, don’t miss popping into cheese shops
- Market day is Friday
10. Radda is famous for its Chianti wines
Radda feels immersed in the Chianti landscape — surrounded by vineyards, with wine woven into everyday life.
It’s less about standout landmarks and more about where you are, right in the heart of Chianti.
Go here if you want to stay in wine country, not just visit it.
My personal recommendations:
- Wander through the medieval street, taking you to the 15th-century Palazzo del Podestà
- 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 feels iconic — dramatic, vertical, and instantly recognizable from a distance.
Yes, it draws crowds, but there’s a reason. The skyline alone makes it one of the most visually distinct towns in Tuscany, earning it a UNESCO-designated status.
Go here if it’s your first time and you want something unforgettable.
My personal recommendations:
- Visit the 15th-century Cathedral, considered one of the best in Tuscany
- Climb the tallest tower, Torre Grosse, and 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
San Quirico d’Orcia feels understated — quietly beautiful without needing attention.
It’s often overlooked, but the surrounding landscape is some of the most scenic in Tuscany, and the town itself remains refreshingly calm.
Go here if you want beauty without the crowds.
My personal recommendations:
- Get your cameras ready, as the scenic drive to the San Quirico area is sublime
- Market day is the 1st and 4th Tuesday of every month
13. Siena is known for its impressive historic sites
Siena feels immersive — a place where you don’t just visit, you step into it.
It’s larger, deeper, and more complex than the surrounding towns, with enough to fill an entire day without rushing.
Go here if you want a full Tuscan city experience with history at every turn.
My personal recommendations:
- Visit the Piazza del Campo and climb Torre del Mangia, the oldest and tallest tower in Italy
- Admire Italy’s most important religious buildings, the Siena Cathedral
- Market day is Wednesday
14. Torrita di Siena is for history lovers
Torrita di Siena feels quiet and unchanged — a town that exists slightly outside the usual flow of visitors.
It’s not trying to stand out, which is exactly why it does.
Go here if you’re curious about places most people pass by.
My personal recommendations:
- Visit the medieval Torrita Castle from the 13th-century castle, which 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
My Final Take on My Favourite Towns in Tuscany
Tuscany isn’t about how many towns you see. It’s about how each one makes you feel.
Some will stay with you for their views. Others for a single quiet moment — a morning espresso, an empty street, the way the light settles at the end of the day.
If you’re planning your route, choose fewer places than you think you need. Give them time. Let the experience unfold slowly.
And if you’re wondering where to base yourself to explore these towns with ease, I’m always happy to share where I stayed — it made all the difference in how this trip came together. Contact me at renee@dreamplanexperience.com, and I might be able to get you a preferred rate.
