Tuscany, a region renowned for its picturesque landscapes, rich history, and delectable cuisine, holds a special allure for travelers from around the globe. It’s a place where you can wander through medieval streets, savor world-class wines, and bask in the beauty of rolling hills and sunflower fields.
From the artistic treasures of Florence to the serene vineyards of Chianti, Tuscany offers a diverse array of experiences that cater to every kind of traveler. In this guide, we will uncover the best cities to visit in Tuscany, helping you plan a memorable journey through one of Italy’s most enchanting regions. For those passionate about wine, don’t miss our guide on the best tuscany itinerary to explore the region and its best wine tastings and wineries in Tuscany.
Top Cities and Towns to Visit in Tuscany
The irresistible charm of Tuscan villages are exactly what couples look for in a romantic getaway. But Tuscany is loved by anyone who spends time there, regardless of the kind of stay.
Florence: The Heart of Renaissance
Florence, the capital of Tuscany, is a treasure trove of art, history, and culture. As the birthplace of the Renaissance, you can explore iconic landmarks like the Uffizi Gallery, the Duomo, and Ponte Vecchio. Beyond its historical significance, Florence offers an impressive array of wine experiences. Visit local enotecas to sample Chianti and Super Tuscans. For a deeper dive, consider a guided wine tour that takes you to nearby vineyards in the Chianti region. You can spend your days wandering through art-filled streets and your evenings enjoying exquisite wine. Discover the best things to do in Florence and be sure to explore the best wine tours and tastings in Florence. Florence perfectly blends rich history with modern wine culture, making it an essential stop on your Tuscan adventure.
Pisa: Beyond the Leaning Tower
Pisa is globally renowned for its iconic Leaning Tower, but this charming town has much more to offer. Beside the customary photo with the tower, you can explore the historic Piazza dei Miracoli, which includes the Cathedral and Baptistery. Pisa’s vibrant university atmosphere also adds a youthful energy to the town. For wine enthusiasts, Pisa serves as a gateway to the nearby wine regions of San Miniato and Montescudaio. Enjoy guided tours that take you through these lesser-known but equally impressive vineyards. You’ll have the opportunity to taste a variety of local wines, making your visit to Pisa a multi-faceted experience. To make the most of your trip, explore our guide on florence to pisa day trip and be sure to check out the best wine tours and tastings in Pisa to complete your itinerary.
Siena: Medieval Charm and Wine
Siena, with its well-preserved medieval architecture, offers a unique atmosphere that takes you back in time. Famous for its historic city center, the stunning Piazza del Campo and it’s majestic cathedral, Siena it’s not just about history; it’s also an unmissable destination for wine lovers. The town is located near some of Tuscany’s top wine regions, including Chianti and Brunello di Montalcino. You can take a short drive to visit these renowned vineyards and enjoy wine tastings that highlight the region’s best offerings. From exploring the town’s ancient streets to indulging in local wines, Siena provides a balanced experience of culture and taste.
For more tips, check out our guide on the best things to do in Siena as well as the best Florence to Siena day trip and don’t forget to book the best wineries to visit in Siena to complete your visit.
Lucca: Hidden Gem for Wine Lovers
Lucca is often described as one of Tuscany’s hidden gems. Encircled by well-preserved Renaissance walls, this charming town offers a more relaxed pace compared to its bustling neighbors. Stroll through its narrow streets and discover picturesque squares, such as Piazza dell’Anfiteatro, and beautiful churches like San Michele in Foro. For wine lovers, Lucca is perfectly situated near the Lucca Hills, a region known for its excellent wines. You can embark on wine tours that take you through this scenic area, offering tastings of the region’s unique varieties. Lucca’s combination of historical charm and proximity to great wine regions makes it a delightful stop on your Tuscan journey. To make the most of your visit, explore the best things to do in Lucca. Additionally, ensure you experience the best wine tours and tastings in Lucca to enrich your trip.
Montepulciano: Wine Lover’s Paradise
Montepulciano is a must-visit for any wine aficionado. Known for its robust Vino Nobile, this hilltop town offers an immersive wine experience that is hard to beat. The town itself boasts an array of Renaissance buildings, charming squares, and panoramic views of the surrounding countryside. When it comes to wine, Montepulciano won’t disappoint. You can visit historic wineries that have been producing top-quality wines for centuries. Take guided tours to learn about the winemaking process, and of course, enjoy tastings of the celebrated Vino Nobile di Montepulciano. The town’s welcoming ambiance and rich wine culture make it a true paradise for wine lovers. For more activities, don’t miss the best Montepulciano wineries to make your visit unforgettable.
Montalcino: The Pinnacle of Wine Excellence
Montalcino is a dream destination for serious wine lovers. Nestled in the heart of Tuscany, this picturesque town is world-renowned for its Brunello di Montalcino, one of Italy’s most prestigious wines. The hilltop town offers stunning views of the surrounding vineyards and countryside, making it a perfect spot for wine tours and tastings. You can visit some of the region’s most famous wineries, where you’ll learn about the meticulous process that goes into producing Brunello. Montalcino itself is filled with historical sites, including the impressive Fortezza di Montalcino and charming medieval streets. The combination of exquisite wine and rich history makes Montalcino an unforgettable destination. For more activities, explore the best Montalcino wineries to make the most of your visit.
San Gimignano: Towers and Tastings
San Gimignano, often called the “Medieval Manhattan,” is famous for its stunning skyline of medieval towers. This UNESCO World Heritage site offers a unique glimpse into Tuscany’s feudal past. As you wander through its cobblestone streets and visit landmarks like the Collegiata di Santa Maria Assunta and Piazza della Cisterna, you’ll be transported back in time.
Beyond its historical allure, San Gimignano is also a haven for wine enthusiasts. The town is renowned for its Vernaccia di San Gimignano, a crisp white wine that has been produced in the area for centuries.
On Winalist, you will find the best San Gimignano wineries to visit and enjoy tastings that showcase this exceptional wine. Don’t miss our guide on the best things to do in San Gimignano.
Volterra: Tuscany’s Timeless Treasure
Volterra is a captivating town steeped in history, dating back to the Etruscan era. Perched on a hilltop, Volterra offers breathtaking views of the Tuscan landscape and is home to a wealth of historical sites, including the Roman Theatre and the Palazzo dei Priori. The town’s ancient charm is complemented by its vibrant cultural scene, with numerous artisan shops and local markets. For wine enthusiasts, Volterra is situated near some of Tuscany’s noteworthy wine regions, providing ample opportunities for wine tours and tastings. You can explore local vineyards that produce high-quality wines, making your visit a delightful experience of both history and flavor.
Greve in Chianti: The Gateway to Tuscan Wines
Greve in Chianti, often considered the gateway to the Chianti wine region, is a must-visit for any wine lover exploring Tuscany. This charming town is known for its picturesque main square, Piazza Matteotti, which is surrounded by quaint shops, cafes, and wine bars. Greve in Chianti serves as an excellent base for exploring the world-famous Chianti Classico wine region. Here, you can embark on wine tours that take you through luxuriant vineyards and historic estates, offering tastings of some of Italy’s finest wines. The town also hosts an annual wine festival, making it an ideal destination for oenophiles. With its combination of beautiful scenaries, rich history, and exceptional wine, Greve in Chianti offers a well-rounded Tuscan experience. For more activities, don’t miss the best Greve in Chianti wineries to enhance your visit.
Arezzo: Between history, culture and wine
Nestled in the eastern part of Tuscany, Arezzo offers a captivating blend of history, culture, and wine that delights every visitor. This lesser-known gem is steeped in antiquity, with roots tracing back to the Etruscan civilization. As you wander through its medieval streets, you’ll encounter stunning landmarks like the Basilica of San Francesco, renowned for its frescoes by Piero della Francesca, and the beautiful Piazza Grande, which hosts the famous Giostra del Saracino jousting tournament.
Beyond its historical treasures, Arezzo is a haven for wine enthusiasts. The surrounding hills are dotted with vineyards producing exceptional wines, including the robust reds of Chianti Colli Aretini and the elegant whites of Valdichiana.
Arezzo’s harmonious mix of cultural richness and wine heritage makes it a must-visit destination for any Tuscan adventure. Among its many delights, one standout experience is dining in the vineyards at Fattoria Di Romignano.
For more tips, don’t miss our guide to the best wineries in Arezzo and be sure to explore our recommendations for things to do in Arezzo.
Good to know before exploring Tuscan Villages
What is the most beautiful village in Tuscany?
On top of being a famous wine village, San Gimignano is also considered as one of Tuscany’s most beautiful and cute villages.
What is the most beautiful part of Tuscany?
The best known and loved area of Tuscany is the one surrounding Florence. However, anywhere you go in Tuscany, you will find the area absolutely stunning. Whether you prefer the coast, vineyards, Medieval villages or large cities, Tuscany has it all. Not mentioning terrific wine and wine activities.
What is considered the heart of Tuscany?
The city of Florence is considered the heart of Tuscany.
What is the best town to stay in Tuscany?
This depends on your personal preferences: do you like quiet cities, cultural cities, medieval villages… In any case, you will find what suits you best as Tuscany will spoil you for choice.
Which is better: Lucca or Siena?
Both of these beautiful cities in Tuscany are worth visiting. Lucca is smaller than Siena, rather quiet and easy to get around. It has one of Italy’s most famous and authentic piazza. Siena is more of a large city. It’s a great choice if you are planning a wine trip in Tuscany, because it is in the Chianti region and close to wine villages such as San Gimignano.