Tuscany, a region of rolling hills, historic cities, and renowned wine estates, offers a unique blend of medieval architecture, artistic heritage, and picturesque countryside.
From the iconic Leaning Tower of Pisa to the charming streets of Lucca, Tuscany is brimming with must-see attractions for first-time visitors. This guide created by the Italian local team at Winalist’s will help you make the most of your trip by highlighting the top 15 must-see sites, ensuring you experience the best of what Tuscany has to offer.
Don’t miss the best Tuscany wine tours for an unforgettable wine experience.
What are the Best Things to Do in Tuscany?
Wander at Florence’s Duomo and Climb the Campanile
Experience the breathtaking architecture of Florence by visiting the Duomo, also known as the Cathedral of Santa Maria del Fiore. Marvel at its stunning facade and intricate designs. Don’t miss climbing the Campanile, the bell tower adjacent to the cathedral. From the top, you’ll be rewarded with panoramic views of Florence’s rooftops and the rolling Tuscan hills.
The climb is steep, but the view is worth every step. Insider tip: Visit early in the morning or late in the afternoon to avoid the crowds. Remember to wear comfortable shoes for the climb. The Duomo complex also includes the Baptistery and the Museo dell’Opera del Duomo, both worth exploring to fully appreciate the site’s historical and artistic significance.
Discover our guide on the best things to do in Florence as well as some top rated Florence wine tours.
Explore the Uffizi Gallery
Discover an unparalleled collection of Renaissance art at the Uffizi Gallery, one of the world’s most famous museums. Located in Florence, the gallery houses masterpieces by artists such as Leonardo da Vinci, Michelangelo, and Botticelli. As you wander through its halls, you’ll encounter iconic works like Botticelli’s “The Birth of Venus” and da Vinci’s “Annunciation.” The gallery’s layout itself is a piece of history, with its long corridors and beautifully adorned ceilings. To make the most of your visit, consider booking tickets in advance to skip the long lines. An insider tip: Visit in the late afternoon when the crowd thins out, allowing for a more intimate experience with the art. The Uffizi also offers guided tours if you wish to dive deeper into the stories behind the artworks.
Visit the Leaning Tower of Pisa
No trip to Tuscany is complete without a visit to the Leaning Tower of Pisa. Located in the Piazza dei Miracoli, this iconic structure is famous for its unintended tilt. The tower, part of a stunning cathedral complex, offers more than just a quirky photo opportunity. You can climb its nearly 300 steps to enjoy a unique view of Pisa and its surroundings. The climb is narrow and spiraling, but it adds to the adventure. Be sure to explore the nearby Cathedral of Santa Maria Assunta and the Baptistery, both architectural marvels in their own right. Insider tip: Try to visit early in the morning or late in the afternoon to avoid peak tourist times. Also, booking your tickets in advance can save you a lot of waiting time. The entire Piazza dei Miracoli is a UNESCO World Heritage site and deserves a leisurely exploration.
Exploring Pisa is an exciting journey filled with unforgettable sights and experiences, learn more in our dedicated guide to the best things to do in Pisa as well as the best Pisa wineries to visit.
Walk to the Piazza del Campo in Siena
Visit the heart of Siena by walking to Piazza del Campo, one of Europe’s most famous medieval squares. Known for its unique shell shape, the piazza is the focal point of Siena’s social and political life. Twice a year, it hosts the thrilling Palio horse race, an event not to be missed if you’re visiting in July or August. As you stroll around the square, take time to admire the Palazzo Pubblico and its Torre del Mangia, which offer stunning views over the city if you’re up for a climb.
The piazza is also a great spot to relax at one of the many cafes, soaking in the vibrant atmosphere. An insider tip: Visit the Fonte Gaia, a beautiful fountain with intricate sculptures located in the square. The Piazza del Campo is a perfect blend of history, culture, and local life.
Discover our perfect Florence to Siena itinerary through the Tuscan vineyards and our guide to the Best things to do in Siena to explore the best Siena wine tours.
Discover San Gimignano’s Towers
Wander through the enchanting medieval town of San Gimignano, renowned for its well-preserved towers that dominate the skyline. Often referred to as the “Medieval Manhattan,” San Gimignano once had 72 tower houses, of which 14 still stand today. These towers were symbols of wealth and power during the Middle Ages. As you explore the town, be sure to visit the Torre Grossa, the tallest tower accessible to the public, offering panoramic views of the Tuscan countryside. The town itself is a UNESCO World Heritage site, filled with charming piazzas, historic buildings, and quaint shops. An insider tip: Try the local Vernaccia di San Gimignano wine at one of the town’s cozy wine bars. Don’t miss the Collegiate Church of San Gimignano, adorned with beautiful frescoes. Strolling through San Gimignano’s narrow streets will transport you back in time and provide a glimpse into medieval life.
On Winalist you will find the best San Gimignano wineries to complete your visit.
Enjoy a Wine Tasting in Chianti
Experience the essence of Tuscany by enjoying one or several Chianti wine tours . Known for its rolling hills and scenic vineyards, Chianti is synonymous with high-quality wines. Visit renowned wineries such as Antinori nel Chianti Classico and Castello di Ama for a guided tour and tasting session. These tours often include a walk through the vineyards, a visit to the wine cellars, and an introduction to the winemaking process.
You’ll have the opportunity to sample various Chianti wines, including the famous Chianti Classico, distinguished by its black rooster seal. An insider tip: Pair your wine tasting with local delicacies like pecorino cheese and prosciutto for a complete culinary experience. Many wineries also offer cooking classes and farm-to-table meals, allowing you to immerse yourself in the region’s gastronomic culture. Booking in advance is recommended, especially during peak tourist seasons.
Stroll through the Val d’Orcia
Explore the picturesque countryside of the Val d’Orcia, a UNESCO World Heritage site known for its stunning landscapes and charming towns. The region, located in southern Tuscany, is characterized by rolling hills, cypress-lined roads, and golden wheat fields. Begin your journey in the town of Pienza, renowned for its Renaissance architecture and delicious pecorino cheese. Next, visit Montepulciano, a hilltop town famous for its Vino Nobile wine and medieval charm. As you stroll through the Val d’Orcia, you’ll encounter idyllic landscapes straight out of a postcard.
An insider tip: Don’t miss the chance to visit the thermal baths in Bagno Vignoni, a unique village with a thermal pool in its main square. Whether you’re exploring by car, bike, or on foot, the Val d’Orcia offers a serene escape into the heart of Tuscany’s natural beauty.
Wander in Montepulciano Village
Immerse yourself in the historic charm of Montepulciano, a picturesque hilltop village renowned for its wine and stunning views. As you wander through its narrow winding streets, you’ll discover Renaissance palaces, ancient churches, and charming squares. Don’t miss the Piazza Grande, the heart of the village, where you can admire the Palazzo Comunale and the majestic Duomo. Wander through the streets and explore the best Montepulciano wineries curated by Winalist.
An insider tip: Climb to the top of the town for a breathtaking view of the surrounding countryside, especially at sunset.
The village is also home to various local artisans selling handmade goods, from ceramics to leather products. Montepulciano offers a perfect blend of history, culture, and enogastronomic delights, making it a must-visit in Tuscany.
Explore the Medieval Town of Lucca
Discover the charm of Lucca, a medieval town famous for its well-preserved city walls and historic center. Start your visit by walking or biking along the tree-lined walls, which offer a unique perspective of the city and surrounding countryside. Inside the walls, you’ll find narrow, cobblestone streets filled with quaint shops, cafes, and historic buildings. Don’t miss the Piazza dell’Anfiteatro, a unique oval-shaped square that was once a Roman amphitheater. Another must-see is the Guinigi Tower, topped with an ancient oak tree and providing panoramic views of Lucca.
The Cathedral of San Martino, with its impressive facade and beautiful interior, is also worth a visit. An insider tip: Visit Lucca during the summer months to experience the Lucca Summer Festival, featuring world-renowned musicians. Whether you’re exploring on foot or by bike, Lucca’s rich history and vibrant culture make it a delightful destination.
To help you make the most of your time in Lucca, Winalist has put together an all-you-need guide to the best things to do in Lucca. So, gear up for a fantastic journey and let’s explore the beauty of Lucca. Don’t forget to complete your trip by discovering the best Lucca wine tours.
Discover the Art and History of Arezzo
Uncover the rich art and history of Arezzo, a Tuscan town brimming with cultural treasures. Start your journey at Piazza Grande, the heart of the city, known for its sloping design and medieval buildings. Here, you’ll find the Palazzo della Fraternita dei Laici, a stunning example of Gothic and Renaissance architecture. Make your way to the Basilica of San Francesco, home to Piero della Francesca’s exquisite fresco cycle, “The Legend of the True Cross.”
This masterpiece is a must-see for art enthusiasts. The Cathedral of San Donato is another highlight, featuring beautiful stained glass windows and impressive frescoes. An insider tip: Visit the monthly Antiques Fair, the largest in Italy, held in Piazza Grande and the surrounding streets. Arezzo’s blend of artistic heritage, historical sites, and vibrant local culture make it an essential stop on your Tuscan adventure.
Don’t miss our guide on the best things to do in Arezzo as well as the best Province of Arezzo wineries.
Have Lunch in the Middle of the Vineyards
Experience the true essence of Tuscany by having lunch in the middle of its picturesque vineyards. Many wineries in regions like Chianti, Montalcino, and Montepulciano offer this unique opportunity. Imagine savoring delicious Tuscan cuisine, paired with local wines, while surrounded by rolling hills and endless rows of grapevines.
Some renowned wineries, such as Castello di Ama and Tenuta Valdipiatta, provide farm-to-table meals where you can enjoy fresh, seasonal ingredients. These lunches often include a guided tour of the vineyard and cellars, giving you insight into the winemaking process. An insider tip: Book your lunch in advance, as these experiences are popular and can fill up quickly. This activity not only satisfies your taste buds but also allows you to connect with the land and culture of Tuscany, creating memories that will last a lifetime.
Walk through the Streets of Cortona
Stroll through the charming streets of Cortona, a picturesque hilltop town that offers a delightful blend of history, culture, and stunning views. Known for its narrow winding alleys and beautiful stone buildings, Cortona is perfect for a leisurely walk. Start your exploration at Piazza della Repubblica, the town’s main square, and make your way to the nearby Piazza Signorelli, home to the impressive Teatro Signorelli. Don’t miss the chance to visit the Diocesan Museum, which houses remarkable artworks, including Fra Angelico’s “Annunciation.” As you wander, you’ll find numerous artisan shops, cafes, and wine bars where you can sample local delicacies.
An insider tip: Climb to the top of the town to visit the Basilica of Santa Margherita and the Fortezza di Girifalco for panoramic views of the Valdichiana valley. Cortona’s enchanting streets and rich history make it a must-visit destination in Tuscany.
Visit the Etruscan Sites in Volterra
Delve into ancient history by visiting the Etruscan sites in Volterra, one of Tuscany’s oldest towns. Known for its rich Etruscan heritage, Volterra offers a fascinating glimpse into this ancient civilization. Start your journey at the Guarnacci Etruscan Museum, which houses one of Italy’s most extensive collections of Etruscan artifacts, including urns, statues, and jewelry. Next, explore the Etruscan Arch, also known as Porta all’Arco, a well-preserved city gate dating back to the 4th century BC. Continue to the Acropolis, where you can see the remains of ancient temples and city walls. Don’t miss the Roman Theatre, beautifully situated on the slopes of Volterra and offering insight into the town’s later Roman era.
An insider tip: Take a walk along the ancient city walls for panoramic views of the surrounding countryside. Volterra’s Etruscan sites provide a captivating journey through time, making it a must-visit for history enthusiasts.
Relax in the Hot Springs of Saturnia
Unwind and rejuvenate by relaxing in the natural hot springs of Saturnia, a hidden gem in the Tuscan countryside. These thermal springs are renowned for their therapeutic properties and stunning natural beauty. The Cascate del Mulino, a series of cascading thermal pools, is the most popular spot, offering warm, mineral-rich waters that flow at a constant temperature of around 37.5°C (99.5°F). The milky blue waters and picturesque setting make for a truly unique experience.
An insider tip: Visit early in the morning or on weekdays to avoid the crowds and enjoy a more tranquil experience. The hot springs are free to access and open year-round. Don’t forget to bring a towel and some water shoes, as the rocky terrain can be slippery. Relaxing in Saturnia’s hot springs is a perfect way to soak in the natural beauty of Tuscany while enjoying a soothing retreat.
Discover the Village of Montalcino
Explore the enchanting village of Montalcino, nestled in the heart of Tuscany and renowned for its world-famous Brunello di Montalcino wine. Begin your visit at the 14th-century fortress, La Fortezza, which offers breathtaking panoramic views of the surrounding vineyards and countryside. Inside the fortress, you can also find a wine shop featuring an extensive selection of local wines. Wander through the village’s charming streets, lined with historic buildings, artisan shops, and cozy cafes. Don’t miss the chance to visit one of the local enotecas to sample Brunello and learn about its unique production process.
An insider tip: Take a short drive to the nearby Abbey of Sant’Antimo, a stunning Romanesque church set amidst rolling hills and olive groves. Montalcino’s rich history, vibrant wine culture, and picturesque scenery make it a must-visit destination for anyone traveling through Tuscany.
Don’t miss the chance to visit Montalcino wineries, carefully selected by Winalist’s local team, where you will be able to tour the cellars and sample exquisite Brunello wines.
Explore the Walled City of Monteriggioni
Step back in time by exploring the walled city of Monteriggioni, one of Tuscany’s most well-preserved medieval fortresses. Encircled by ancient walls and fourteen towers, this small village offers a glimpse into history with its cobblestone streets and historic buildings. Start your visit by walking along the walls, where you can enjoy panoramic views of the surrounding countryside. Within the walls, you’ll find the quaint Piazza Roma, the heart of Monteriggioni, featuring a charming church and several cafes. An insider tip: Visit the Monteriggioni in Arme Museum to learn about the history of the fortress and see medieval armor and weapons.
The city also hosts an annual medieval festival, Monteriggioni di Torri si Corona, where the village comes alive with costumed performers, artisans, and medieval-themed activities. Monteriggioni’s timeless ambiance and historic significance make it a must-see destination in Tuscany.
Good to Know to Plan Your Trip to Tuscany
What are the best hotels to stay in Tuscany?
When planning your stay in Tuscany, consider these top hotels for an unforgettable experience:
– Belmond Castello di Casole (5-star luxury): Nestled in the Tuscan countryside, this hotel offers luxurious accommodations, a stunning infinity pool, and exceptional dining options.
– Il Borro Relais & Châteaux (5-star luxury): Owned by Ferruccio Ferragamo, this estate combines history and elegance with modern amenities, featuring a medieval village, vineyards, and a state-of-the-art spa.
– Castello Banfi – Il Borgo (5-star boutique): Located in the Montalcino wine region, this boutique hotel is part of a renowned winery. Enjoy wine tastings, gourmet dining, and breathtaking views of the vineyards.
Each of these hotels provides a unique blend of luxury, history, and exceptional service, ensuring a memorable stay in Tuscany. Whether you prefer a countryside retreat or a historic estate, these accommodations offer the perfect base for exploring the region.
What are the best traditional restaurants in Tuscany?
For an authentic taste of Tuscany, dine at these top traditional restaurants:
– Osteria di Passignano: Located in the heart of Chianti, this Michelin-starred restaurant is part of the Antinori wine estate. Enjoy classic Tuscan dishes made with local ingredients, paired with exceptional wines.
– Antica Macelleria Cecchini: In Panzano, this legendary butcher shop turned restaurant offers a unique dining experience. Chef Dario Cecchini serves up traditional meat dishes, including the famous Bistecca alla Fiorentina.
– Trattoria Mario: Situated in Florence, this family-run trattoria has been serving delicious, home-cooked meals since 1953. Known for its hearty ribollita and tender Florentine steak, it’s a must-visit for traditional Tuscan cuisine.
Each of these restaurants offers a genuine Tuscan dining experience, highlighting the region’s culinary heritage. Reservations are recommended, as these popular spots can fill up quickly.
What is the best time to visit Tuscany?
The best time to visit Tuscany depends on your preferences for weather, events, and crowd levels. Spring (April to June) is ideal for mild temperatures, blooming flowers, and fewer tourists. It’s a great time for exploring the countryside and enjoying outdoor activities. Summer (July to August) brings warm weather and lively festivals, but also larger crowds and higher prices. If you prefer a quieter experience, visit in early September, when the weather is still pleasant but the summer crowds have dwindled. Autumn (September to October) is another excellent choice, especially for wine enthusiasts, as it’s harvest season and the vineyards are bustling with activity. The fall colors add to the landscape’s beauty. Winter (November to March) is the off-season, offering the lowest prices and fewer tourists, though some attractions may have limited hours. Tuscany’s mild winters make it a cozy, serene getaway during this time.
How to get around Tuscany?
Getting around Tuscany is relatively easy, with several transportation options available. Renting a car is the most flexible way to explore the region, allowing you to visit rural areas and smaller villages at your own pace. Tuscany’s scenic drives, such as the Chiantigiana Road, offer stunning views and charming stops along the way.
Public transportation is also a viable option, especially for visiting major cities like Florence, Siena, and Pisa. Trains connect these cities and many smaller towns, offering a convenient and affordable way to travel. Buses are available for areas not serviced by trains, although they may be less frequent.
For a more leisurely experience, consider biking through the Tuscan countryside. Many towns have bike rental shops, and there are numerous cycling routes to explore. Lastly, guided tours provide a hassle-free way to see the highlights of Tuscany, with transportation, entry fees, and expert guides included.
What are some must-try dishes in Tuscany?
Tuscany is renowned for its simple yet flavorful cuisine, rooted in local ingredients and traditional recipes. Here are some must-try dishes:
– Bistecca alla Fiorentina: A thick, juicy T-bone steak, typically from the Chianina breed of cattle, grilled to perfection and served rare.
– Ribollita: A hearty vegetable and bread soup, made with kale, beans, and leftover bread, simmered to develop rich flavors.
– Pappa al Pomodoro: A thick tomato and bread soup, seasoned with garlic, basil, and olive oil, perfect for a comforting meal.
– Panzanella: A refreshing summer salad made with stale bread, tomatoes, cucumbers, onions, and basil, dressed with olive oil and vinegar.
– Cantuccini: Traditional almond biscuits, often enjoyed dipped in Vin Santo, a sweet dessert wine.
These dishes showcase the essence of Tuscan cooking, emphasizing seasonal produce and quality ingredients. Make sure to savor these culinary delights during your visit.
