Searching for the most beautiful towns in Tuscany to add to your Tuscany travel itinerary? Keep reading!
Tuscany is one of Italy’s most beautiful and romantic regions known for its rolling hills, rows of Cypress trees and charming towns. No trip to Tuscany is complete without visiting some of the magical towns scattered around, and lucky they are pretty close together so visiting 4 or more is more than achievable in just a few days in the region!
Discover the awe-inducing beauty that is Tuscany by visiting one or more of the most beautiful towns in Tuscany.
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14 Most Beautiful Towns in Tuscany
Florence – the capital of the Tuscany region – is easily one of the most beautiful towns in Tuscany and possibly even the world! Its charm and magic radiate through the streets that are home to some of the world’s most magnificent pieces of architecture. Find here the famous Florence Cathedral – The Duomo, Basilica of San Lorenzo, Basilica of Santa Maria Novella and much more!
A visit to Florence is a must when touring Tuscany to see and experience one of the most popular and iconic cities in Italy. Be sure to budget around 2 days so you can see all of the beauty this city has to offer. Plus, if you only have time to do a quick Tuscany tour staying in Florence and doing day trips is a great option.
Siena is a purely WOW city. The medieval brick buildings, hilly streets, old town squares and historic charm all combine to make it one of the most beautiful cities in Tuscany. Siena is a place that will majorly surprise you and is a must-visit. The best thing about Siena is it’s a great place to set up a central base in Tuscany where you can easily rent a car and venture out into the rolling hills of Tuscany quickly and easily.
Pienza is a quaint and charming town in Southern Tuscany conveniently located in the breathtaking Val d’Orcia valley of Tuscany. Val d’Orcia is arguably the best place to visit in Tuscany for the iconic rolling hills and rows of cypress trees. While Pienza is a historic and super beautiful town with delicious Italian restaurants, local shops and amazing views.
Right near Pienza is also where you will find the famous filing spot for Gladiator!
San Gimignano is a small stone-walled city located in the hills of Tuscany. It is continually rated as one of the most beautiful towns in Tuscany that has a charm like no other. San Gimignano is famous for its medieval architecture complete with huge towners, cobblestone streets, and old town squares. A visit here will have you feeling like you’ve stepped back in time in the best way possible.
Lucca is one of the most well-preserved Renaissance towns in Tuscany known for its stone walls encircling the old historic town. This is one of the most beloved cities in Tuscany that is a must-add to your itinerary! It is can be explored in just half a day or you can stay here a few days and explore the rest of Tuscany on day trips from here.
Montepulciano is exactly what you think of when you imagine a postcard-perfect town within the rolling hills of Tuscany. This medieval hilltop gem is one of the most beautiful towns in Tuscany the offers the old streets, authentic restaurants, and breathtaking views over the vineyards of Tuscany.
Cortona is the main artistic and cultural center of Tuscany complete with a Renaissance-era cathedral, Roman roads and an Archaeological Park. It is one of the most beautiful towns in Tuscany that is great to visit for experiencing a blast from the past with amazing food and a buzzing atmosphere.
Pitigliano is one of the most mesmerizing and beautiful towns in Tuscany located within the hills of the region. The old stone architecture, fortified walls and cliff views all combine to make it feel like you’ve stepped back in time. This town also has a very strong Jewish Heritage and is called “Little Jerusalem” because in the 16th century many people from the Jewish community fled Rome to Pitigliano.
You may recognize the name Volterra if you are/were a Twilight fan and this Tuscany town is every bit as magical as the book itself. With its expansive valley views, old stone buildings, and cobblestone streets Volterra is a place of pure charm and beauty.
Monteriggioni is a completely walled town in Tuscany known for its intense wall fortifications and watchtowers. This town can be found in the very famous Chianti wine region of Tuscany, so if you want to enjoy some wine tasting without a far drive this is the ideal place for you! Head to Monteriggioni to discover the 13th-century Church of Santa Maria, the old town gates and deep history.
Arezzo is one of the most beautiful cities in Eastern Tuscany famous for its Arezzo Cathedral. This cathedral is home to stunning painted ceilings and a beautiful 15th-century fresco of Mary Magdalene. Arezzo can be reached in just one hour from Florence and is well worth the day trip to immerse yourself in the beauty and history of Tuscany.
Montalcino is a beautiful hilltop town located near Siena. With its sweeping views over the valleys below, it was once a very strategic spot on the road to Rome so it holds great significance in Tuscany. From Montalcino, you can enjoy the stunning views of Val d’Orcia and enjoy the beauty of the city alongside them.
San Quirico d’Orcia
San Quirico d’Orcia is a commune in Tuscany. It is a very small town in Tuscany – mostly just one road but is still well worth a visit. The beautiful town sits atop a hilltop and offers stunning views of the very famous Val d’Orcia region of Tuscany.
Pisa is one of the most famous and beautiful towns in Tuscany made famous for its leaning tower of Pisa. This charming Italian Tuscan Town is much more than the leaning tower of Pisa like its beautiful architecture, amazing food and more. Check off viewing the leaning tower of Pisa off your bucket list by heading here ASAP!
Where to Stay in Tuscany
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With so many beautiful towns in Tuscany, it can be hard to pick which ones to visit and which to skip!
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so many beautiful places to visit! i love the architecture and the history of it all- one for the list for sure!!
Oh, I would love to slow travel through Tuscany! Such a beautiful area with lovely towns to visit and explore.
Great roundup! I was surprised at how much I loved Volterra. It is such a unique place and relatively non-touristy. Siena was exactly how you described (wow!). I would love to see a horse race there one day.
My daughters going there in a month! I’ll send this to her. Thanks!
Such a comprehensive list! I’ve been to a few of these places but clearly there is so much more to see. Your post truly makes me want to plan an extended visit to this region of Italy.
Jenn | By Land and Sea says
The last few weeks I’ve been wanting to go to Italy so bad! Until the travel situation levels out a bit more, I’ll just enjoy this great roundup of amazing places!