The region of Tuscany might very well be one of the most famous in Italy. Known for its dreamy landscapes of rolling hills and lush vineyards, the Tuscan countryside is worth the hype.
However the region’s jewels, in my opinion, are not the bucolic views or vineyards, but the enchanting villages that dot its hills. Each of these towns offers a trip back in time, as their unique heritage has been kept alive in their buildings, cobbled alleys, and rich culture, and they deserve to be on your Tuscany itinerary.
I’m Italian and was born and raised just one hour away from Florence, in the city of Bologna, but even I as a local still get mesmerized by the landscapes and the oh-so-cute and charming villages in Tuscany.
From the hilltop fortresses of San Gimignano and Monteriggioni to the serene beauty of Pienza, the villages showcase the quintessential landscapes of the Italian countryside. They’re also a great place to immerse yourself in the most famous wine country, sampling wine varieties and visiting local cellars.
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How to Get Around Tuscany
▶️ The best way to get around Tuscany is by car. Having your own vehicle gives you the freedom to explore the countryside, taking in its scenic views and visiting the villages at your own pace.
Some of the towns and cities in the region have ZTL zones in their historic center, so you’d have to park your car outside. If you plan to visit quite a few villages, however, having a car is highly convenient.
➤ I usually use Discover Cars to compare car rental prices online and book in advance. ➥ COMPARE PRICES HERE
Discover Cars is an online booking service that offers a wide range of rental options from various agencies in Cancun. This makes it easier to find a rental car that suits your budget and needs. I particularly like their cancelation policy.
Typically, with Discover Cars, you can cancel your booking for free up to 48 hours before the pickup time. This is a much more generous cancelation policy than other platforms. It’s always important, however, to read the specific terms and conditions of your rental agreement. Policies can vary based on the rental company and the rate you choose.
▶️ Tuscany also has an efficient train network, mainly connecting major cities like Florence, Pisa, and Siena. However, you’ll need to take the local buses to get into rural areas and smaller towns.
▶️ If you prefer not to drive, for a hassle-free experience, you may consider joining a tour that includes a visit to your desired village. If you decide to stay in Florence and go on day trips from there, I’ve written an article about the best Tuscany tours from Florence that you should check out as well.
Most Charming Villages in Tuscany
Pienza
Pienza is a rather small town in southern Tuscany, immersed in the awe-striking region of Val d’Orcia in the Province of Siena.
It’s one of the most captivating towns in Tuscany, and known as the perfect Renaissance city for being a prime example of brilliant urban planning.
Its UNESCO-listed historic center houses Piazza Pius II, an architectonic masterpiece designed by Pope Pius II in the 15th century.
Pienza’s location in the heart of the valley, surrounded by lush rolling hills, also does wonders for its irresistible charm!
As you stroll along the winding streets, you’ll find beautiful stone houses adorned with colorful flowers, spectacular facades, and outdoor cafés. The Pienza Cathedral, Palazzo Piccolomini, and the city walls are unmissable stops in the old town.
You should also try Pecorino Cheese, Pienza’s most famous product, and indulge in a delightful meal of Pici pasta paired with Tuscan wine.
For a delectable experience of Tuscan cuisine, dine at Sette di Vino. The Osteria La Porta, L’Osteria Baccus, and Trattoria La Chiocciola are spectacular alternatives!
How To Get There: Pienza is 72 miles (116 km) south of Florence, and the drive along the A1/E35 will take you slightly over 1.5 hours.
There’s no direct way to reach Pienza from Florence using public transportation. You can take a bus from Firenze Autostazione to Siena, and from there bus 144 toward Buonconvento. There, you’ll change to line 112, which takes you to Pienza in about 30 minutes.
▶️ A great alternative is joining the Pienza and Montepulciano Small-Group Tour From Siena. You’ll travel through the scenic landscapes of Tuscany to visit Pienza, followed by a scrumptious lunch at a local farm. Spend the afternoon in Montepulciano, a hilltown best known for its delicious wine. ➥ BOOK IT HERE
San Gimignano
San Gimignano is arguably the most popular village in Tuscany. Located close to Florence, this medieval hilltop offers the perfect outlook of the rolling landscape around it.
San Gimignano’s major highlight is its ancient towers, built by patrician families as a symbol of their wealth and power. There were 72 towers originally, and 14 of them still stand today, providing the unique skyline the town is so proud of.
This beautiful village in Tuscany has a vibrant historic center, listed as a UNESCO World Heritage Site. It features a triangular square, Piazza della Cisterna, and magnificent architecture surrounding it.
It also boasts a maze of narrow cobbled alleys lined by a plethora of artisan shops, trattorias, and cafés, as well as a few wine bars. The town is known for the Vernaccia di San Gimignano, a celebrated crist white, so a tasting session at a local cellar is pretty much a must.
For glorious views, go up Torre Grossa, one of the perfectly preserved medieval towers. Don’t forget to cap off the trip with gelato from the award-winning Gelateria Dondoli!
Blending historical splendor, culinary prowess, jaw-dropping vistas, and crips wines, San Gimignano is an unmissable stop in Tuscany.
How To Get There: San Gimignano is only 36 miles (58.3 km) from Florence, about an hour’s drive.
Traveling by train will take you approximately an extra hour, as the train will drop you off at Poggibonsi – San Gimignano. From there, you’ll need to take Autobus AT025 to the hilltop town. Tickets cost 12€ at the time of writing.
▶️ A good alternative is to join a Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery. You’ll have a guided tour around Siena, and free time in San Gimignano and Pisa, before indulging in wine tasting and local cuisine. ➥ BOOK IT HERE
Montepulciano
Montepulciano is one of the famous Tuscan towns perched on a hilltop, overlooking the vibrant countryside.
It’s also home to incredible Renaissance heritage, and it features grand architecture and medieval streets that are a dream to get lost in. As you stroll along its alleys, you’ll come across a wealth of artisan shops, impressive palazzi, and local eateries.
The town is backed by the bucolic landscapes that surround it, offering stunning postcard views on every turn.
Montepulciano is particularly known for its prestigious Vino Nobile, an exquisite red wine produced from the Sangiovese grapes that grow in this part of Tuscany. You can enjoy tastings in the local wineries and enotecas, and get a bottle or two to take home.
A few cellars worth checking out for wine tasting include Gattavecchi Winery, Contucci, and Cantina Ercolani.
Highlights that you shouldn’t miss include Piazza Grande, the Cathedral of Santa Maria Assunta and the Palazzo Comunale.
The city walls, the Church of San Biagio, and the Porta al Prato Gate are also worth a visit. For astounding panoramic views, head to Vaduta Panoramica! You’ll see how the authentic Tuscan scenery of rolling hills, olive groves, and vineyards unfolds before your eyes.
How To Get There: Montepulciano is 67 miles (108 km) south of Florence, and the drive takes 1.5 hours along the A1/E35.
It’s not very easy to reach the town using public transportation. If that’s your only option, though, the fastest way is to take bus ST6 to Bettolle, and from there take bus ST3 to Porta delle Farine stop in Montepulciano.
▶️ You can also book the Full Day Tour to Val d’Orcia and Gladiator’s Fields with Wines to discover the major highlights of the region. Visit Pienza, Montalcino and Montepulciano, and relish cheese and wine tastings at various wineries. An expert guide will be with you, but you’ll also benefit from free time in each location. ➥ BOOK IT HERE
Arezzo
The enchanting city of Arezzo brims with history and architectural treasures, most of which date back to the Middle Ages. Its vibrant culture, delicious local cuisine, and bustling markets make it a must-visit in the region of Tuscany.
Piazza Grande is the bustling heart of Arezzo, equipped with sloping pavement, outdoor cafés, and historic buildings. Here you’ll find the beautiful Romanesque Church Santa Maria della Pieve and Palazzo delle Logge.
The narrow alleys snake through Arezzo’s old town, lined by artisan workshops, stores, and beautiful facades. As you stroll around the old town, make sure to stop at Basilica of San Francesco to admire its Renaissance frescoes.
If you visit on the first Sunday of the month, you’ll be able to browse through the treasures of an antiques market as well. Don’t leave Arezzo without trying its typical sweet, Gatto Aretino!
How To Get There: Arezzo is 47 miles (36 km) southeast of Florence. The drive takes 1 hour and 20 minutes via A1/E35.
You can alternatively take a direct train from Florence Santa Maria Novella to Arezzo. The journey takes between 1 and 1.5 hours, and tickets cost 11€.
Monteriggioni
One of the most beautiful towns in Tuscany is Monteriggioni. Perched on a gentle slope, it’s completely enclosed by perfectly preserved fortress walls.
Dating back to the Middle Ages, they have fourteen watchtowers and offer glorious views of the Chianti countryside from the top. Stepping foot into Monteriggioni truly feels like going back in time!
The town also features narrow cobblestone streets and very historical buildings. The quaint alleys lead to the main square, Piazza Roma, where most of the town’s action takes place.
There you’ll find trattorias, shops, and cafés with outdoor seating areas, as well as the majestic Church of Santa Maria Assunta.
If you plan your visit for July, you might get to participate in Monteriggioni’s medieval festival ‘‘di Torri si Corona’’. It showcases bustling markets, music shows, and reenactments, effectively taking you back in time to the Middle Ages.
How To Get There: Monteriggioni is 38.5 miles (62 km) south of Florence, about an hour’s drive via Raccordo Autostradale Firenze – Siena.
There’s a direct bus – line 131 from Autolinee Toscane – that takes you from Firenze Autostazione to Colonna di Monteriggioni. The trip takes an hour and 15 minutes, but departures are not frequent.
An alternative is catching a bus to Colle di Val d’Elsa and from there taking line 130 to Monteriggioni, or joining a tour.
▶️ This San Gimignano, Siena, and Chianti Wine Tour from Florence is a full-day excursion that takes you to a prime location in Tuscany. You’ll visit Siena with a guide, drive through the scenic hills of Chianti, and spend time in San Gimignano and Monteriggioni. ➥ BOOK IT HERE
Bagno Vignoni
A lesser-known but equally charming town is Bagno Vignoni, nestled right in the heart of Val d’Orcia. This tiny town – it’s home to less than 40 people! – is renowned for its thermal baths.
The historic pools, fed by volcanic springs, were very popular during the Roman era due to their health properties. It’s believed that quite a few emperors, including the infamous Lorenzo de’ Medici, bathed in the town’s waters.
The central square, Piazza delle Sorgenti, features a massive thermal pool with steaming water at 120 F (49ºC). Bathing in it is no longer allowed, but the pool remains the most awe-striking landmark in town!
You’ll find cafés and restaurants all around it, so it’s a good spot to relax with a coffee and take in the scenery.
There’s more to Bagno Vignoni than springs, though! Its historic center brims with quaint shops, cozy trattorias, and a few spas where you can soak in the mineral-rich waters.
How to Get There: Bagno Vignoni is about 77 miles (125 km) south of Florence, a 2-hour drive.
While there’s a direct bus line from Firenze Autostazione – line B23 – it only operates a few times a week, so I’d highly recommend visiting with a car.
Cortona
Atop a hill in the Chiana Valley stands Cortona, one of the most historical villages in the Tuscan Countryside.
Its Etruscan heritage is very strong, and so is the influence of medieval and Renaissance culture, present in its architecture and art. The center of Cortona, as it happens with most Tuscan towns, is Piazza della Repubblica.
It’s a bustling square dominated by Palazzo Comunale and its clock tower, and it’s the perfect place in town for people-watching with a drink in hand.
There’s an abundance of artisan workshops, cafés, and traditional trattorias lining the cobbled streets, so make sure you go wandering around town. The Diocesan Museum and the Basilica di Santa Margherita are two iconic attractions to visit there.
The panoramic views over the valley, with its olive groves, lush vineyards, and rolling hills are also a must-see. There are plenty of vantage points throughout Cortona, so you won’t miss them!
How to Get There: Cortona is 72 miles (116 km) south of Florence, and the drive takes approximately 1.5 hours along the A1/E35.
You can take a train from Florence Santa Maria Novella, and get to Cortona in approximately 2 hours. Tickets cost anywhere between 14€ and 29€.
▶️ You can also visit the town with this Siena, Cortona, Montepulciano & Val D’Orcia From Florence. It’s a super comprehensive-full-day trip that allows you to visit multiple locations in Tuscany, including the enchanting Cortona. Aside from time in each destination, you’ll enjoy a wine and cheese tasting and lunch at an ancient cellar and farm. ➥ BOOK IT HERE
Volterra
Perched on a rocky hill is Volterra, one of the towns and villages in Tuscany that still retains its Etruscan heritage. Its winding streets take you past incredibly well-preserved structures, including an Etruscan Gate and Roman Theater.
The town’s architecture blends influences from various periods, and one of the greatest examples is Piazza dei Priori.
Dominated by the striking Palazzo dei Priori, Tuscany’s oldest town hall, the square is surrounded by medieval buildings. It’s an unbeatable spot to enjoy an aperitivo and some people-watching!
Volterra is especially known for its alabaster craftsmanship, which was already in full swing in the 3rd century BC, and was mainly used to carve funeral urns. Make sure to pop by a workshop to witness how the artisans work it, or shop handmade pieces at the local boutiques!
Another interesting landmark in Volterra is the Guarnacci Etruscan Museum, a real treat for history lovers as it boasts one of the largest collections of Etruscan antiques.
Volterra’s rich history and customs are enhanced by its culinary wonders. When in town, don’t miss the pappardelle pasta with wild boar sauce, and zuppa alla Volterrana at one of the many trattorias.
How to Get There: Volterra is around 49 miles (78.8 km) from Florence, and the drive takes 1 hour and 40 minutes via Strada Provinciale 4 Volterrana.
It’s also possible to travel by public transportation, although the journey will take double the time. You’ll have to take a train to Cecina, and from there catch bus Autobus FI255 to Volterra.
▶️ The Volterra and San Gimignano: a taste of medieval Tuscany! is a great alternative to visiting the city. It’s a full-day trip that takes you into the heart of Tuscany with private transfers and a customized itinerary. You’ll get to take your time discovering the historic centers of Volterra and San Gimignano and its main attractions. ➥ BOOK IT HERE
Other Enchanting Villages & Towns in Tuscany
If you have time to spare, these are other iconic villages to visit in Tuscany:
▶️ Montalcino, a town boasting a gorgeous historic center and the birthplace of the world-class Brunello di Montalcino wine.
▶️ The city of Siena, where the famous Palio di Siena takes place twice a year. No visit to Tuscany is complete without a trip to this historical, culturally rich city!
▶️ Pisa, home to the Leaning Tower of Pisa and other architectural wonders in Piazza dei Miracoli.
▶️ Greve in Chianti is one of the prettiest towns to visit in the Chianti countryside. It’s especially known as the area where the Chianti Classico wine is produced.
