The Tuscany region in Italy is a beautiful area, vast with rolling hills, sunflower fields, vineyards, and hilltop towns. No matter where you find yourself in this area, it is going to be amazing. On our first Tuscany adventure we decided to set base in Florence (which is in Tuscany) and explore the countryside from there. This list is our personal favorites of the towns of Tuscany we explored within close distance to Florence.
If it’s your first time exploring Tuscany – this list of Tuscan towns will give you a great starting point and will take you through several of the main areas and wine regions of Tuscany. We saw all of these towns (excluding Pisa) in one day! Although doable, we recommend spreading the towns out over two days so you can fully enjoy and not be rushed!
Our Favorite Towns of Tuscany!
San Gimignano
San Gimignano, a name I have spent countless hours trying to pronounce, is a Medieval Manhattan with over 14 towers covering the towns three hill tops. The city has many local markets throughout its stone-paved and ivy covered streets. Be sure to eat dinner at one of the many restaurants promoting dinner in a garden terrace overlooking the sunset across the rolling Tuscan hills.
Siena
Being one of Tuscany’s largest (and busiest) cities, there are many public transportation options to get to Siena. The town has much to offer behind it’s impressive walls – with many shops, museums, restaurants, and activities to keep a full schedule while visiting. Also, the city is in a central location to make day trips north to Chianti and south to Val d’Orcia. If you are traveling in busy season – this town can be one of the most crowded in the area!
Chianti Region
The Chianti region is the area south of Florence and north of Siena. Chianti is one of Italy’s most recognized and favorite red wine producers. However, because the region is vast and lacks public transportation, it is not over-run with tourists! So, it is a perfect destination to relax and experience Italian culture. We suggest renting a car, because the train from Florence to Siena misses many of the must-sees of Chianti.
Castellina in Chianti
Castellina is one Chianti’s smallest towns and also one of the few not encased behind a fortress wall. Its castle, Rocca di Castellina, is worth the walk through the strange museum to get to the top! The ancient architecture is lined with art and history, and the views from the tower are worth the drive to the small town. The municipality of Castellina is entirely within the Chianti Classico wine zone.
Radda in Chianti
Radda is the smallest town we visited while in Tuscany, but it offered some the most incredible views – our entire reason for stopping (and of course the wine). The foothills of Radda are rich with the famous grapes of the region and offer a picturesque view over the valley.
Val d’Orcia Region
Val d’Orcia is a small region just south of Sienna, it has slightly different scenery than Chianti but equally beautiful. While this region also has incredible wine, you will find more crops here than grapes. All I could think about while strolling through the endless fields was the ending scene of the Gladiator as Russel Crowe returns to his home; that is the perfect depiction of Val d’Orcia.
Montalcino – one of our favorites of the favorites!
Montalcino is a medieval town overlooking the Val d’Orcia Natural Park behind its fortress walls. Within the foothills of the town you can find endless sunflower fields that make for incredible photo-ops. It is somewhat of a maze getting to the town center, so be sure to stay on the main road (which is the only paved road up the hill). We ventured off the beaten path and found ourselves on a gravel road, crawling up a narrow cliff with no guard rails – views were incredible, though!
We arrived early morning and strolled through the slow-paced stone streets enjoying the never-ending Tuscan views from atop the hill. While it is not a prominent tourist destination, the streets are lined with arts and crafts, cafes, restaurants and wine bars. We had one of our favorite and least expensive meals in Tuscany at Les Barriques. Montalcino is world renowned for it’s wine, Brunello to be precise, so if you have time take a tour of the vineyards! This place is worth the visit to see true Tuscany without all the crowds!
Pisa
Just east of Florence, on the route to Cinque Terre and Portofino, make a quick stop at the Leaning Tower of Pisa and the Cattedrale di Pisa. Just to note, the town itself is not the great. So, only planning on stopping to see this one sight and get your iconic photo holding up the tower!
Hope you enjoy your excursions through the Towns of Tuscany! Check back soon for a city guide to Florence AND insight into the five villages of Cinque Terre!
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~ Zain Hartman
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Could you recommend some places to stay?
Hi Ana – I apologize for the late response – this comment did not send us a notification! We can absolutely recommend some places to stay in Tuscany. If you would like to send us an email or submit a contact form with your trip info (towns/dates) we would love to provide recommendations!
Have a great time in Tuscany and Happy Travels!
Brooke