Tuscany has a way of stealing your heart. Whether it’s the rolling vineyards, hilltop towns, or the fact that every meal feels like an event. If you’re planning a trip and wondering where to start, here’s my take on the Tuscan towns that left the biggest impression.
Most people know Tuscany for its beautiful landscapes, wineries, and well-known historical towns, but did you know there are 279 towns, each with their own distinctive personality? While I have visited quite a few, I’d love to try to visit them all, but that would mean I’d probably need to spend almost a year in Tuscany. While I’m TOTALLY on board for that, I don’t think my husband, or our bank account would be down for that. However, about 10 years ago, after a couple glasses of wine, my husband agreed that after we retire, we could live in Italy for a year. Needless to say, I’ve never let him forget it, so not all is lost. Perhaps I will be able to visit every Tuscan town one day!
Here’s a look at my five favorite towns (I didn’t include Florence this time — it deserves its own spotlight, which you can find in my Florence travel guide here.)
#1 CORTONA
Cortona is a beautiful hill town with a charming and lively atmosphere. Cortona gained a lot of popularity after the book “Under the Tuscan Sun” was published. Then, after they made it into a movie, I, like millions of other women, became enamored with the dreamy romance of Cortona.
The atmosphere in Cortona is warm and welcoming. Its old town is filled with little shops and eateries, many with outdoor seating. One evening, as we were having dinner, an orchestra gathered on the steps of Town Hall in the main square and began playing. It was so surreal and magical that it felt like perhaps we were going to witness an engagement or the filming of a movie scene. It made what was already an amazing summer evening, a night to remember.
Great Restaurants to Try
If you have the opportunity to enjoy an evening in Cortona, book dinner at Ristorante La Loggetta or La Bucaccia, both excellent.
Where to Stay
As for accommodations, Cortona is a great place to base yourself if you plan to explore Tuscany. There are many options ranging from studio apartments to castle-like villas that sleep 20 people. If you’re traveling with a group, then I’d highly recommend Villa Caprile, a beautiful villa in the hills of Cortona. You can read my review about our wonderful week at this villa here.
For a lovely hotel stay, check out Monastero di Cortona Hotel & Spa. It’s a former monastery turned boutique hotel, with amazing views, a relaxing spa, and an easy walk to the main square. It’s one of those spots that feels peaceful but still close to everything.
If you’re just planning to visit on a day trip, Cortona’s old town is not too big and can be visited in several hours.
What to Do
Be sure to see the Duomo, the museum, and the Church of San Francesco. If you love to shop, there are lots of little boutiques where you can pick up local treasures, along with food shops selling fresh bread, olives, and wine.
If you have time, walk up (or drive) to the Fortezza del Girifalco for panoramic views of the Val di Chiana valley — it’s a bit of a climb, but totally worth it.
Stop by the Etruscan Academy Museum if you’re into history — Cortona has deep Etruscan roots, and the collection is surprisingly good for such a small town.
If you’re visiting in summer, check the calendar for local events like Cortona on the Move, a popular international photography festival that brings exhibits all over town.
And of course, don’t skip the simple stuff — grab a gelato and wander Cortona’s cobblestone streets at golden hour. It’s when the town feels its most magical.
Cortona has that perfect mix of small-town charm and lively energy — it’s easy to see why so many people fall in love with it.
#2 SIENA
Siena — my favorite Tuscan town (Cortona is a very close second) — is brimming with charm. As you enter the historic center, a UNESCO World Heritage site, it feels as though you’re walking straight into the Middle Ages.
A Great Hotel in the City Center
My husband and I spent four nights in Siena and used it as a base to explore Tuscany. We stayed at The Grand Continental, a luxury 5-star hotel that is not only beautiful but ideally located in the heart of the historic center. It was an excellent stay — and honestly, the location can’t be beat.
Siena’s Famous Palio
Unbeknownst to us, our stay was during the festivals of the 17 Contrade (neighborhoods). During this event, the streets come alive with decorations, flags, and music. Each district is dressed to the nines in their Contrada’s colors and costumes, marching through the streets while drummers drum and flag bearers lead the way.
These celebrations are the lead-up to Siena’s most famous event — the Palio, a centuries-old horse race that takes place right in Piazza del Campo, the city’s main square. It happens twice a year (in July and August) and draws huge crowds. If you’re hoping to see it, be sure to book accommodations and tickets many months in advance.
A Few Things To Do
Siena’s historic center is full of boutiques, galleries, and great restaurants — it’s a fun place to shop or simply wander (and yes, I did plenty of both).
If you’re feeling energized, climb the 300 steps to the top of the Torre del Mangia, and enjoy views of the landscapes around Siena. Also, be sure to visit Siena’s underground aqueducts, as well as the Santa Maria della Scala museum.
Should you have time, consider taking a cooking class in Siena. My husband still talks about the Pici carbonara he had in Siena as one of the best pasta dishes he’s ever had (Pici is a thick pasta noodle and is typically served with a boar or pork ragù).
If possible, spend at least one night in Siena’s old town center — it’s magical once the day-trippers leave. But if that’s not an option, plan to spend at least 5 or 6 hours exploring. There is a direct train that goes from Florence to Siena, making day trips easy if you’ve based yourself in Florence. The ride takes about 1.5 hours and costs $10-15.
#3 SAN GIMIGNANO
If there ever was a medieval storybook town, San Gimignano is it. As you approach the hilltop town, it’s impossible not to notice the 14 towers standing prominently in the distance (at one time there were 72). Have your camera ready — you’ll want photos from almost every angle.
San Gimignano is small but brimming with character, with terracotta rooftops, quaint buildings, and curvy cobbled streets. The town can get busy during the day, but don’t let that stop you — it’s worth it.
There are plenty of little shops, including several selling the region’s famous wild boar products.
Where to Lay Your Head
Brian and I spent two nights here, and while it was busy and energetic during the day, it is sleepy and quiet at night. We stayed at Il Nido di Anna, a small B&B that is simple yet makes for a lovely stay in this little village. Plus, the owner Renata was wonderful, the location made it easy to wander the town in mornings and evenings, and our room had AC (which is a non-negotiable of my hubby).
If you’re planning how much time you’ll need for a day trip, San G can be seen in 2 or 3 hours. If you’d really like to get a feel for the town, consider spending a night here.
One of the Best Restaurants Ever
I cannot wrap up without mentioning Cum Quibus restaurant. The service is excellent, atmosphere is intimate, and the wild boar paradelle ragu with truffles is out of this world! Brian and I both agree that our meal here is in our top three EVER!!! We were blown away by this restaurant, so much so, that we cancelled our dinner reservation for the following night so that we could come back to Cum Quibus again.
Getting There
San Gimignano isn’t directly on a train line — it’s one of those classic Tuscan hill towns that you can only reach by bus or car. Here’s how it typically works if you’re using public transportation:
- Take the train to Poggibonsi-San Gimignano station, which is on the main Florence–Siena line.
- From there, it’s about a 25–30 minute bus ride (local buses run fairly regularly during the day).
If you’re driving, it’s much easier. You’ll find parking lots just outside the historic walls, and from there you can walk up into town.
#4 PIENZA
Even smaller than San Gimignano, Pienza is home to around 2,100 residents. But what it lacks in size, it more than makes up for in charm. Seriously, it’s literally adorable.
A UNESCO World Heritage Site, Pienza sits between Montepulciano and Montalcino, making it easy to combine these three towns in a single day trip. The town is famous for its stunning landscapes, Renaissance architecture, and pecorino cheese — so if you love cheese like me, you’re in for a treat.
What to Do
Start with Corso il Rossellino, the main street running through town, and make your way to Piazza Pio II, the central square named after Pope Pius II, who was born here. Around the square, you’ll find the Duomo, Palazzo Piccolomini, Palazzo Borgia, and Palazzo Comunale — each worth a peek.
Branch off into the side streets to discover charming buildings, small artisan shops, and scenic corners. Don’t worry about getting lost — Pienza is tiny, so it’s nearly impossible.
I’d describe Pienza as adorable, lovely, and romantic. Others seem to agree, as the town boasts charmingly named streets like Via del Bacio (Kiss Street) and Via dell’Amore (Love Street), reflecting its romantic atmosphere.
Food & Drink
Pienza is a paradise for cheese lovers. Be sure to stop at La Buca delle Fate or Antica Macelleria Falorni to try pecorino in all its glory. You can also find small cafés and enotecas for a glass of local wine and a light snack while enjoying the views.
Where to Stay
If you’d like to stay overnight, there are a handful of charming boutique hotels and guesthouses. A few favorites:
- Hotel Corsignano – Right in the heart of town, great views of the Val d’Orcia, and walking distance to everything.
- Relais Il Chiostro di Pienza – A beautifully restored former convent with peaceful gardens and classic Tuscan vibes.
Staying overnight gives you the bonus of seeing the town quiet down after the day-trippers leave — the golden hour light on the Renaissance buildings is magical.
Getting There
- By car: This is the easiest way. Pienza is about a 40-minute drive from Montepulciano and 1.5 hours from Florence. Parking is available just outside the historic center.
- By bus: There are buses from nearby Montepulciano and Chianciano Terme, but schedules can be limited, so plan ahead if you’re not driving.
#5 MONTEPULCIANO
Montepulciano has much of the Renaissance architecture typical of Tuscany, but this walled hill town has a more regal and grand charm than others. It is located in the beautiful Val d’Orcia region and offers breathtaking views of the surrounding vineyards and landscapes.
If you love wine, Montepulciano is a must. It’s world-famous for its Vino Nobile di Montepulciano, a medium-bodied red made from at least 70% Sangiovese grapes — basically liquid happiness for wine lovers.
What to Do
Wine Tours: There are many wineries in this area, so if you’d like to sample a few, I recommend doing a wine tour. We did our tour with Franco Faddo, a great guide that has a passion for these regional wines. He is a wealth of information and has relationships with nearly all of the boutique wineries in the area.
Self-guided tasting: If a guided tour isn’t your thing, check out Contucci Cantine in the historic center. This Contucci family has over 1,000 years of history of wine production. In addition to tasting the wines, you can order some nibbles, and take a self-guided tour of the underground cellar.
Annual event: Montepulciano comes alive in late August for the Bravio delle Botti, a barrel-rolling competition through the steep cobblestone streets. Each Contrada competes, and the week is filled with parades, dancing, flag-throwing, and general festive energy.
Shopping and wandering: Explore specialty shops and galleries for Tuscan souvenirs — from hand-painted landscapes to Italian-made jackets, handbags, and ceramics.
Lunch & people watching: Grab a seat at one of the trattorias in Piazza Grande. The vibe is lively and perfect for people-watching.
Bell Tower views: After lunch, climb the Bell Tower for sweeping views — or take the elevator if you’ve indulged a bit too much! Either way, the views are incredible.
Where to Stay
- Albergo Il Marzocco – A boutique hotel right in the heart of town, walking distance to shops, restaurants, and Piazza Grande. Charming rooms with terraces overlooking the valley.
- La Locanda di San Francesco – A lovely, intimate hotel with traditional Tuscan décor, perfect for a romantic overnight stay.
Getting There
- By car: The easiest way. Montepulciano is about 1.5 hours from Florence and 45 minutes from Pienza. Parking is available near the historic center.
- By bus/train: Take a train to Chiusi-Chianciano Terme, then a bus (30 minutes) to Montepulciano. Public transport works but is less flexible than driving.
Whether it’s tasting wines, exploring cobbled streets, shopping for local treasures, or soaking in the landscapes, Montepulciano is a Renaissance gem not to be missed.
Should I stay in Florence and Day Trip to Tuscan Towns?
If you have less than four days, I recommend basing yourself in Florence and taking day trips. If you have more time, consider staying a few days in Florence and few days in another location, such as Cortona or Siena.
You can read my one-week Tuscan Itinerary here and my Florence travel guide here.
Tuscany’s Festivals, Events & Holidays
If you’ve ever shown up in Italy only to find every shop and restaurant closed for a holiday, you know how frustrating it can be. Here is a short list of Tuscany’s biggest annual festivals and national holidays so you can plan your trip with confidence—whether you want to join the local celebrations or avoid the crowds altogether. It’s all about timing your visit right and knowing what to expect when you get there.
When to Visit Tuscany
Tuscany is beautiful year-round, but the experience really depends on the season. If you’re deciding when to go, here’s what to expect throughout the year:
Spring (April–June)
This is one of the best times to visit. Wildflowers are blooming, vineyards are green again, and the weather’s mild — usually in the 60s and 70s°F. It’s perfect for sightseeing, wine tasting, and road trips before the summer crowds arrive.
Summer (July–August)
Tuscany gets hot — sometimes hitting the 90s°F — and very busy, especially in major towns and along the coast. Still, it’s when most festivals happen, so if you love energy and long, lively evenings outdoors, this might be your time. Just book early and expect higher prices.
Fall (September–October)
Another ideal season. The weather cools off, vineyards turn golden, and it’s harvest time — meaning wine festivals, truffle fairs, and plenty of local food events. It’s busy but not overwhelming, and the countryside looks incredible.
Winter (November–March)
Quieter and more affordable. You’ll find fewer tourists and cozy stays in smaller towns. Some attractions in the countryside may close, but cities like Siena, Pisa, and Lucca stay active. It’s also truffle and olive oil season, so it can be a delicious time to visit if you don’t mind cooler weather.
In Short:
If you want great weather without the crowds, plan for May–June or September–October. Those months hit the sweet spot between comfort, scenery, and local events.
Final Thoughts
I’ve only covered five towns here, but there are so many more worth exploring in Tuscany. I’ll keep adding to this guide over time, but towns like Volterra, Pisa, Lucca, Arezzo, and Greve (to name just a few) are all wonderful too. If you have extra time to explore, take it slow and enjoy discovering some of Tuscany’s other hidden gems.
Copyright 2025 Laugh Lines and Travel Sign
Contact: laughlinesandtravelsigns@yahoo.com
Some of the links in this post are affiliate links, which means I may earn a small commission if you make a purchase — at no extra cost to you. Thanks for supporting the blog!
Related Blog Posts…..
- Contact: laughlinesandtravelsigns@yahoo.com
- Disclosure & Privacy Policy
- Copyright 2025 Laugh Lines and Travel Signs