Best Towns in Tuscany

Cattedrale Di Santa Maria Del Fiore​ - Florence, Italy

Situated in central Italy, Tuscany is a region famous for its beautiful endless green landscapes, artistic legacy and more. From undulating vineyards and medieval hilltop towns to lively markets and timeless art, Tuscany offers a unique blend of pure beauty and human creativity. In this article, we’ll explore some of the best towns in Tuscany, each with its own charm and distinct character. Whether you’re seeking the peacefulness of the countryside or the lively atmosphere of historic centers, these towns promise to fascinate and inspire.

Rent a car Tuscany

Rent a car Tuscany

The best way to experience Tuscany and the surrounding area is to rent a car! We recommend booking well in advance using price comparison sites like rental cars if traveling in the peak summer season.

Prettiest towns in Tuscany

San Gimignano

San Gimignano, Tuscany, Italy

San Gimignano is one of our favourite towns in Tuscany. It is a picturesque town set between the Sienese hills and the sunny Val d’Elsa hills. Enclosed by thirteenth-century walls, it retains its medieval charm and stands as a cherished gem in Tuscany. It is also called Medieval Manhattan due to its striking skyline of medieval towers.

We will never forget the gelato from Gelateria Dondoli which is known all over the world and visited by a large number of celebrities.

Find out the best things to do in San Gimignano.


Piazza Dei Priori - Volterra

Volterra is a hilltop town southwest of Florence. Imagine a charming hilltop town with ancient Etruscan ruins and a museum overflowing with artifacts. Plus, there’s a gorgeous cathedral with a jaw-dropping marble entrance, and a medieval palace with panoramic views from its bell tower.

Unlike many touristy towins in Tuscany, Volterra offers a delightful escape. It’s just as charming and medieval, but with a quieter, more authentic atmosphere.


Piazza Della Repubblica​ - Cortona, Tuscany

Cortona is a charming Etruscan village nestled in the Tuscan hills. This town in Tuscany, known for its breathtaking views, delicious food, and friendly locals, holds a special place in our heart. Cortona’s rich history is evident in its architecture and daily life, despite a growing expat community. The town’s authenticity, unchanged for generations, makes it a truly special place.


Church Of The Madonna Di San Biagio​, Montepulciano, Tuscany

Montepulciano’s reputation as a world-class wine region has turned it into a beloved Tuscan destination. A day trip lets you explore charming Montepulciano: stroll the main Corso to reach the grand Piazza Grande, and delve into the town’s history with a wine cellar tour. Montepulciano offers more than just world-class wines! Unlike other wine towns, it boasts stunning medieval architecture, a rich history, breathtaking views, and delicious food, making it a well-rounded destination for any traveler.


Lucca Cathedral, Tuscany

We can’t recommend Lucca enough! It’s a must-visit for any traveler, and we were completely charmed by our time there. Lucca offers a wealth of walls, squares, palaces, and artworks. Lucca’s history unfolds through its buildings. Towering over the town is the iconic Torre Guinigi, a 45-meter (125ft) Romanesque-Gothic marvel with a surprising rooftop garden. 

Unlike the bustling tourist hubs of Florence, Siena, and Pisa, this Tuscan treasure remains a peaceful haven, perfect for those seeking a more relaxed and authentic Italian experience.


Monteriggioni Gates

A jewel of Tuscany, Monteriggioni is a tiny, charming village encased within remarkably well-preserved 13th-century walls. Built by the Republic of Siena as a strategic defense against Florence, Monteriggioni offers a glimpse into Tuscany’s fortified past.


While Monteriggioni may be a micro-village with just 50 residents tucked within its walls, its charm is undeniable. A day trip in Monteriggioni is a must. Enjoy a walk along the ramparts, a peek around town, and a stop at the museum, can be done in under an hour, making it a perfect pitstop for history buffs.


The Siena Cathedral (Duomo Di Siena)​

This city stuns with its medieval architecture, boasts world-class Renaissance museums, and houses an iconic cathedral. It’s a place that leaves a lasting impression on all who visit. Enclosed within a stunning 1,000-year-old wall, this city is famous for two things: its bi-annual Palio horse race, a thrilling medieval tradition, and its abundance of awe-inspiring medieval architecture.

Explore the stunning Duomo complex, wander the charming city center, climb the Torre del Mangia for breathtaking views, delve into history at Palazzo Pubblico, and admire the beauty of Santa Maria della Scala. Check the best thing to do in Siena.


Pienza offers the best of both worlds: a stunning historical center brimming with charm, and a convenient location for exploring the captivating Val d’Orcia valley. Pienza’s charm is best savored slowly. While it’s a walkable town, don’t underestimate its appeal! Wandering its streets, soaking in the history, and indulging in the local delights can easily fill a delightful half-day. 

Pienza is also the crowned capital of Pecorino cheese. Thanks to the unique milk from a special breed of Sardinian sheep grazing in the Val d’Orcia, Pienza’s Pecorino boasts an unforgettable flavor and aroma. Don’t miss a taste while you’re there!


One of the most unique towns is Tuscany is Pitigliano which is carved into the volcanic rock. It is a breathtaking Tuscan town that demands to be explored. Perched majestically on a cliff, this postcard-perfect village is known as “Little Jerusalem” due to its vibrant Jewish community that dates back to the 15th century. We highly recommend dedicating a few hours to getting lost in its charming streets and soaking up its unique history.


Florence, the heart of Tuscany, is a treasure trove of art, architecture, and culture.  This city is where the Renaissance blossomed, leaving behind a legacy of awe-inspiring masterpieces. The iconic Duomo cathedral, with its soaring red dome, is a symbol of Florence’s artistic prominence.

Three days in Florence is the sweet spot, especially for first-timers. Rushing through the city in less time risks feeling overwhelmed and missing the true magic of its cultural treasure.


Montalcino is a picturesque town that offers delightful walks, stunning views, and a relaxed atmosphere, perfect for unwinding and soaking up the Tuscan charm.

It’s also a great place to go wine tasting. Brunello di Montalcino DOCG, Rosso di Montalcino DOC, Moscadello di Montalcino DOC, and Sant’Antimo DOC are exclusively made in Montalcino.


When you hear about Pisa, the Leaning Tower is the first thing that comes to your mind. However, Pisa offers so much more. Beyond the crowds snapping photos of the tilted wonder, lies the heart of Pisa. Explore the charming local areas, where hidden gems and authentic Italian life await. This city boasts over twenty historic churches, each whispering tales of faith and artistry. Grand medieval palaces and elegant bridges spanning the Arno River complete the picture, making Pisa a captivating destination for history buffs and explorers alike.

Greve in Chianti

Consider Greve in Chianti your gateway to Tuscany’s soul. This quaint town, often the first stop on the famed Chianti Road, isn’t just about world-class wines. Beyond the vineyards, Greve offers a captivating blend of art, history, and culinary delights. Explore charming streets, discover hidden treasures, and indulge in the flavors that define Tuscany. Greve is the perfect introduction to everything this region has to offer.

Radda in Chianti

Radda in Chianti, Tuscany

This picturesque village nestled in the heart of Chianti offers a world away from your daily routine. Imagine strolling through quaint cobbled streets, soaking up the breathtaking panoramas, and immersing yourself in the local culture. Radda’s calendar overflows with events, while the restaurants tantalize your taste buds with authentic Chianti cuisine prepared with fresh, local ingredients.


Arezzo offers a captivating blend of history and artistic treasures. While a half-day allows you to see the main sights, Arezzo rewards those who linger. Arezzo offers something for everyone. History buffs can delve deeper into the past at museums, while shoppers can browse the bustling antique market held monthly. So, whether you’re here for a quick visit or a more in-depth exploration, Arezzo promises an unforgettable experience.


Nestled in the Garfagnana region, a northwestern gem of Tuscany within Lucca’s province, Barga reigns supreme as the most captivating hilltop town – definetely a hidden gem in our list with the best towns in Tuscany. This area boasts a landscape unlike any other – a kaleidoscope of natural wonders offering hundreds of ways to explore the outdoors.

Barga boasts a unique culinary treasure: Farina di Neccio. This flour, crafted from locally-sourced chestnuts that carpet the Tuscan woodlands, forms the base of two must-try delicacies. For a savory treat, indulge in Neccio, a flatbread that perfectly complements local cheeses and meats. Craving something sweeter? Castagnaccio awaits! This cake combines the rich, nutty flavor of Farina di Neccio with the delightful crunch of walnuts and pine nuts.

Castiglione della Pescaia

This gem of the Maremma region stuns with its dramatic beauty. A majestic ancient fortress perched on a hilltop gazes out over the sparkling turquoise waters of the Tyrrhenian Sea. Imagine long stretches of pristine beaches and the refreshing embrace of pine groves – that’s the magic of Castiglione della Pescaia. This seaside town offers a perfect escape for those seeking to unwind amidst breathtaking scenery.


Nestled like a jewel amidst the verdant embrace of Val di Cornia, Suvereto enchants with its medieval charm. Encircled by ancient walls, the village unfolds a treasure trove of history. Wander through characteristic cobbled streets lined with timeworn stone houses and admire the architectural beauty of historic buildings and evocative churches.

Suvereto’s name whispers of the surrounding landscape – a tapestry of endless forests. Chestnut trees mingle with oaks, while the presence of cork trees hints at the region’s natural bounty.

Casole d’Elsa

Tuscany’s crown jewel, Casole d’Elsa, offers a peaceful escape compared to the throngs of tourists that crowd other Tuscan hotspots. This impeccably preserved hilltop village exudes civic pride, with its trademark town walls, breezy public spaces, and quality attractions. Nestled near Siena, Casole d’Elsa’s enchanting location adds to its charm. At 417 meters above sea level, the village boasts breathtaking panoramas of rolling green hills adorned with olive groves and vineyards. Beyond the village walls, a mesmerizing landscape unfolds, inviting exploration and promising a truly unforgettable Tuscan experience.


Nestled roughly 20 kilometers west of the famed Chianti hills, Certaldo beckons with a unique dual identity. Certaldo Alto, almost entirely untouched by time offers a captivating glimpse into the medieval era. We parked the car at the funicular base and opted for a charming ride up to the old town. From the top, a gentle climb led us to the museum. The real reward came next – a short walk to the left unveiled a breathtaking panorama! Rolling fields and forests stretched out before us, culminating in the distant silhouette of San Gimignano’s iconic towers.


Fosdinovo is a charming medieval town nestled in Tuscany, northern Italy. Located in the province of Massa and Carrara, near the Liguria border, Fosdinovo boasts a well-preserved historic center, an ancient castle, and stunning panoramic views of the surrounding countryside.

What truly sets Fosdinovo apart is its designation as a Bandiera Arancione (Orange Flag) town. This prestigious award, presented by the Touring Club Italia, recognizes towns that excel in tourism experiences. To receive this honor, towns must meet strict criteria including historical and artistic heritage, environmental sustainability, accessibility, and the overall quality of the tourist welcome. So, you can be sure that a visit to Fosdinovo will be a delightful and enriching experience.


Immerse yourself in Tuscany’s hidden gem, Montefioralle. This charming village, officially recognized as one of Italy’s most beautiful villages, transports you to another world despite being just outside Florence in the heart of Chianti wine country. With its stone buildings adorned with flowers and cobbled walkways whispering tales of times gone by, Montefioralle offers an authentic escape unlike the bustling crowds of Florence.

Bagno Vignoni

Nestled amidst the rolling hills of Tuscany’s Val d’Orcia, Bagno Vignoni enchants as a charming village perched atop a scenic hill. This popular tourist destination is famed for its naturally heated springs, a treasure that has drawn visitors for centuries. Imagine soaking in the warm waters, surrounded by breathtaking Tuscan scenery


Collodi, a medieval village bathed in history, will leave you spellbound. Cobblestone streets, worn smooth by centuries of footsteps, wind between houses that retain their charming medieval character. Traces of the past abound, from the remnants of imposing fortifications to the gateways that once guarded the town.

This village holds a special connection to Carlo Lorenzini, the author who penned the beloved children’s tale of Pinocchio.


Elba, an island paradise in the Tuscan Archipelago National Park, is a dream destination for a relaxing getaway. While renowned for its beaches and historical significance as Napoleon’s exile in 1814-1815, Elba’s magic goes beyond the surface.

Unlike a typical seaside resort, Elba offers an unparalleled island experience. Imagine the invigorating charm of the sea, fresh air filling your lungs and the sound of waves gently lapping at the shore. Elba’s soul is a captivating blend of Tuscan and island life, reflected in its welcoming inhabitants, its mouthwatering cuisine, its pleasant climate, and of course, its stunning beaches.


Livorno, a Tuscan port city steeped in maritime history, offers a vibrant tapestry of culture and cuisine. Livorno’s charm lies in “New Venice,” a canal quarter built in the 17th century. Imagine canals, a touch of Venice, and the octagonal, frescoed Church of Santa Caterina.

Best towns to stay in tuscany

Few of the many great towns to base yourself in Tuscany: 

Siena: Medieval charm, art & history in a walkable city. Explore central Tuscany & nearby Chianti/Val d’Orcia wine regions. Escape summer crowds with a countryside stay; charming winter wonderland.

Florence: Florence is the heart of Tuscany and a must-visit for any art lover. With its world-famous museums like the Uffizi Gallery and the Accademia Gallery, there’s enough Renaissance art to keep you busy for days. Florence is also a great base for exploring the surrounding countryside, with towns like Siena, Pisa, and Lucca all within easy reach.

Lucca: Lucca is a charming walled city with a relaxed vibe. Great for exploring northern Tuscany by bike.

Montepulciano: This beautiful hill town in southern Tuscany is famous for its Vino Nobile wine and proximity to Val d’Orcia’s rolling hills, vineyards, and medieval villages.

San Gimignano: San Gimignano is a good base for exploring central Tuscany, with towns like Siena and Florence within easy reach.


What Tuscan villages are accessible by train?

Florence can be your hub for exploring Tuscany by train! Several charming towns boast direct connections, making day trips a breeze. Pisa, Lucca, and Siena are all within easy reach, allowing you to experience their unique offerings in a single day or linger for a longer stay. For a more diverse itinerary, consider San Gimignano, famed for its medieval towers, or Livorno, a port city with a unique “New Venice” canal district.

How many days do you need in the Tuscan countryside?

Seven days in the Tuscan countryside promises the perfect blend of exploration and relaxation. It’s enough time to delve into the region’s soul, venturing beyond the surface.

What is the best way to explore Tuscany?

Tuscany’s treasures are best discovered by car or guided group. For independent spirits, a car unlocks endless freedom – meander through idyllic countryside roads, stumble upon hidden gems, and stop for breathtaking photo ops whenever the mood strikes. Guided group tours offer a curated experience, ensuring you see the must-see sights and benefit from expert insights. Whichever path you choose, Tuscany promises an unforgettable adventure.

What is the best month to visit Tuscany?

Spring (April-May) & Fall (September-October): These shoulder seasons boast pleasant weather, vibrant landscapes, and fewer crowds. Imagine comfortable temperatures ideal for exploration, blooming flowers in spring or fall foliage, and shorter wait times at popular attractions.

June: June offers a taste of summer with longer days and warm weather, perfect for enjoying outdoor activities. However, be prepared for larger crowds and potentially higher prices.

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