Most Beautiful Towns in Tuscany You Shouldn't Miss

Rolling hills, cypress-lined roads, golden vineyards, and medieval towns perched on hilltops—Tuscany feels like it stepped straight out of a painting. While Florence and Pisa often steal the spotlight, it’s the smaller towns that truly capture the region’s soul. These timeless gems offer history, beauty, and a peaceful rhythm of life that’s hard to forget.
Last updated: 1106.2025

Tuscany’s towns offer a glimpse into the heart of Italian culture. Each village tells its own story, from Renaissance art and Roman ruins to world-class wine and slow food traditions.

Whether you’re road-tripping through the countryside or planning a day trip from Florence, these picturesque towns offer an authentic experience far from the crowds.

Is Tuscany Worth Visiting?

Absolutely—Tuscany is not only worth visiting, it’s one of the most enchanting and diverse regions in all of Italy. Whether you’re dreaming of Renaissance art, charming countryside escapes, world-famous wines, or timeless hilltop towns, Tuscany truly delivers on every front. It’s a region where you can spend the morning exploring centuries-old cathedrals and museums in Florence, enjoy a leisurely lunch in a medieval piazza, and finish the day watching the sun set over vineyards with a glass of Chianti in hand.

Tuscany is also ideal for travelers seeking a slower, more immersive experience. From hands-on cooking classes and truffle hunts to peaceful bike rides through olive groves and soaking in hot springs under the stars, the region offers a deep connection to Italian culture and landscape. Whether it’s your first trip to Italy or your fifth, Tuscany has a way of stealing hearts—and bringing travelers back again and again. For those looking to experience this timeless charm in an authentic and meaningful way, the Tuscany Heritage Tour is the perfect gateway.

Where Is Tuscany Located in Italy?

Tuscany is a region in central Italy, stretching from the rugged Apennine Mountains in the northeast down to the Tyrrhenian Sea in the southwest. It borders several other regions, including Liguria and Emilia-Romagna to the north, Umbria and Marche to the east, and Lazio to the south. Its strategic location makes it easily accessible from major Tuscany cities like Rome, Venice, and Milan, either by high-speed train or by car, and it’s often included in broader Italian itineraries.

The capital of Tuscany is Florence (Firenze), an art and culture hub that’s considered the birthplace of the Renaissance. Other well-known cities in Tuscany include Pisa, Siena, Arezzo, and Lucca, along with dozens of picturesque towns like San Gimignano and Montepulciano scattered throughout the rolling countryside. With its varied geography—mountains, valleys, vineyards, and coastline—Tuscany offers an incredibly rich and balanced Italian experience all in one region.

What Are the Top Things to Do in Tuscany?

There’s no shortage of unforgettable things to do in Tuscany, no matter your interests. Start in Florence, where you can explore Renaissance masterpieces at the Uffizi Gallery, climb to the top of the Duomo, and stroll across the historic Ponte Vecchio. In Siena, discover Gothic architecture, wander through the fan-shaped Piazza del Campo, and learn about the famous Palio horse race that takes place each summer. Then head to Lucca, where you can walk or bike along the perfectly preserved Renaissance walls and enjoy a quieter, elegant charm.

Venture into the countryside for a wine tasting tour through the Chianti region, or explore the golden hills and cypress-lined roads of the Val d’Orcia, home to some of Tuscany’s most iconic views and postcard-perfect towns like Pienza and Montalcino.

For relaxation, soak in the natural thermal springs of Saturnia or Bagno Vignoni, or take a cooking class in a rustic farmhouse to learn the art of Tuscan cuisine.

Don’t miss sampling local specialties like handmade pici pasta, wild boar, pecorino cheese, and, of course, Tuscany’s world-renowned wines like Brunello di Montalcino and Vino Nobile di Montepulciano. Whether you spend your days wandering through vineyards, discovering medieval towers, or simply enjoying a slow lunch under the Tuscan sun, every corner of this region offers something magical.

Most Beautiful Towns in Tuscany You Shouldn’t Miss

San Gimignano

Often referred to as the “Medieval Manhattan” due to its skyline of stone towers, San Gimignano is one of Tuscany’s most iconic towns. Once a thriving stop along the Via Francigena pilgrimage route, it’s now a UNESCO World Heritage Site that feels frozen in the 13th century. The town’s well-preserved medieval architecture, narrow cobbled streets, and artisan shops create an atmosphere that’s both historic and romantic. Don’t miss climbing the Torre Grossa for a panoramic view of the surrounding countryside, tasting local Vernaccia di San Gimignano wine, and trying gelato at Gelateria Dondoli, frequently ranked among the best in the world.

Montepulciano

Easily connected by the Monterosso - Vernazza Cinque Terre trail (which takes about 1 hour and 15 minutes on foot) is alluring Vernazza. The little town is home to numerous historic sights, including the famous Doria Castle which dates back to the 11th century, its tower that's set on the edge of a cliff is a popular photo stop. Other landmarks to see in Vernazza are the Santa Margherita di Antiochia church as well as the Marconi Square. A stroll down to the harbor with lined finishing boats will also grant you with spectacular spots for taking pictures. To truly experience the beauty of the region, consider joining the Incredible Umbria & Tuscany tour — a perfect way to explore the heart of Italy.

Pienza

Designed by Pope Pius II in the 15th century as the “ideal Renaissance city,” Pienza is small in size but rich in history and harmony. Located in the heart of the Val d’Orcia, it offers not only spectacular views of the rolling Tuscan countryside but also a stunning example of early urban planning. The town is also famous for its pecorino cheese, which you can sample in almost every shop along its charming streets. Try to visit during the Fiera del Cacio cheese festival in September, when locals celebrate with tastings, music, and the quirky cheese-rolling contest in Piazza Pio II.

Cortona

With ancient Etruscan origins and a setting made famous by the book and film Under the Tuscan Sun, Cortona is a romantic hillside town full of personality. Its stone alleyways, historic churches, and artisan boutiques give it a warm and welcoming vibe. Art lovers will appreciate the Museo Diocesano, which houses works by Fra Angelico and Luca Signorelli, while hikers will enjoy the trail up to the Basilica di Santa Margherita and Fortezza Medicea for sweeping views. It’s the perfect mix of history, art, and everyday Tuscan life.

Volterra

Often overlooked in favor of nearby San Gimignano, Volterra offers an equally rich (and far less crowded) experience. This walled hill town has deep Etruscan roots, visible in its archaeological museum and ancient gate Porta all’Arco. Wander through the quiet streets to discover alabaster workshops, Roman ruins including a well-preserved theater, and a peaceful main square anchored by the Palazzo dei Priori, Tuscany’s oldest town hall. Volterra’s dramatic landscapes and weathered architecture give it a slightly mystical air—perfect for slow travel and quiet reflection.

Lucca

Unlike many Tuscan hill towns, Lucca is flat and incredibly walkable, making it a favorite for families and casual explorers. The town is best known for its intact Renaissance walls, which now serve as a tree-lined promenade encircling the historic center—perfect for a morning stroll or bike ride. Within the walls, you’ll find a maze of narrow lanes, elegant churches, and charming piazzas. Be sure to visit Piazza dell’Anfiteatro, an oval square built on the site of an ancient Roman amphitheater, and climb Torre Guinigi, famous for the oak trees growing from its rooftop garden.

Montalcino

This hilltop town in southern Tuscany is the home of Brunello di Montalcino, one of Italy’s most prestigious wines. Surrounded by vineyards and olive groves, Montalcino is a haven for wine enthusiasts. Tour historic wineries, enjoy tastings with a view, and dine on local specialties like pici pasta with wild boar ragù. The 14th-century fortress at the top of town offers some of the best views in the region, and nearby Abbazia di Sant’Antimo, a stunning Romanesque abbey, is a peaceful detour worth making.

Greve in Chianti

Nestled in the heart of the Chianti wine region, Greve is the quintessential wine village, with easy access to dozens of surrounding wineries. Its unique triangular piazza is lined with porticoes, wine shops, and inviting cafés, making it the perfect place to spend a lazy afternoon. Every Saturday, the piazza hosts a lively weekly market, and each September, the Chianti Classico Wine Festival brings producers from across the region to showcase their best vintages. Visit the Museo del Vino for a bit of history, then set out to nearby hamlets like Panzano and Radda in Chianti for even more scenic beauty.

Tuscany’s beauty goes far beyond its famous cities. Charming towns like San Gimignano, Montepulciano, Pienza, Cortona, and Montalcino invite you to slow down, take in the views, and savor life one glass of wine or bowl of pasta at a time. Whether you’re planning a few day trips or a longer adventure, each stop offers a deeper connection to the soul of Italy. For a seamless way to experience these highlights and more, the Bella Italia tour offers an unforgettable journey through the heart of the country’s most beloved regions.