Can’t-miss things to do in Tuscany

World-class wines. History-making cities. Jaw-dropping art. Mouthwatering food. Breathtaking landscapes. It’s no wonder Tuscany is one of the most popular regions to visit in Italy. 

So with all these superlatives, how do you begin to discover the essence of Tuscany? This guide should give you some ideas.

What you’ll learn:

• Tuscany makes some of the most acclaimed wines in the world.

• The region’s cities, towns and villages offer visitors a chance to immerse themselves in history and spectacular views.

• The Tuscan capital of Florence has something for everyone, from art and architecture to food and fashion.

• Capital One’s Venture X and Venture travel rewards credit cards are built for travel, with benefits that can elevate your next adventure.

Tuscany’s climate and geography produce some of the world’s best-known wines, including Montalcino, Chianti, Vino Nobile di Montepulciano and Super Tuscans. And there are many ways to enjoy them. Here are a few. 

Wine routes connect vineyards, farmhouses, villages and artisans, offering a taste of Tuscany you can enjoy by bike, on foot or on horseback. There are currently about 15 trails in Tuscany, including:

• Colline Pisane Wine Trail: This route winds through the villages, hills and chestnut groves of the Pisa countryside. Travelers on this route can enjoy Chianti and other wines—plus sample extra-virgin olive oil, white truffles and pecorino Toscano.

• Orcia Wine Trail: The whole Val d’Orcia area is a UNESCO World Heritage site. This trail runs through much of it, from Abbadia San Salvatore through Montalcino to Pienza. Along with Orcia wines, travelers can also enjoy cured meats and saffron along the way.

• Maremma Wine Trails: The secluded Maremma region has three wine trails. The Montecucco Wine Trail is known for its namesake Montecucco wine. The Colli di Maremma Wine Trail showcases several wines, including Ansonica Costa dell’Argentario and Morellino di Scansano. And the Monteregio di Massa Marittima Wine Trail is dedicated to Monteregio wine.

Wine museums can take oenophiles on an immersive journey through the history and stages of local wine production, with tasting opportunities, multimedia displays and even virtual reality as part of the experience.

Some Tuscan wine museums you might want to visit include:

• Temple of Brunello, Val d’Orcia: This converted convent celebrates Brunello di Montalcino, one of Italy’s best-known and most expensive red wines.

• Vine and Wine Museum, Rufina: In the cellars of a 16th-century villa, you can chart the tradition of Chianti winemaking in the Val di Sieve.

• Vernaccia di San Gimignano Wine Experience, San Gimignano: Take classes, explore exhibits and taste the Vernaccia wine variety in a 14th-century fortress.

Of course, many individual Tuscan vineyards are open to visitors too. You can do your own research to find those that look interesting to you. But here are three that Winetourism.com recommends:

• Azienda Agricola Malenchini, Bagno a Ripoli: Malenchini Farm makes organic red, rose and dessert wines from the Sangiovese, Merlot and Cabernet Sauvignon grapes it cultivates over 17 hectares.

• Azienda Agricola Villanoviana, Bolgheri: Villanoviana Farm grows Merlot, Petit Verdot, Viognier grapes and more using organic viticulture techniques.

• Camigliano Castle: A 13th-century fortress transformed into a winery, Camigliano produces organic wines from the Sangiovese Grosso vine.

Rolling hills and vineyards are just part of Tuscany’s appeal. The region’s more populated areas are equally charming and picturesque. From imposing walled cities to quaint hillside villages, here are just a handful of historic Tuscan spots worth a day trip or longer.

A trip to Siena, with its signature red-brick architecture, is like stepping back in time to the Middle Ages. Inside the city’s ancient ramparts lie a number of noteworthy sights, including:

• Piazza del Campo: Siena’s historic main square. Twice a year, it becomes an arena for the Palio di Siena, a thrilling and sometimes treacherous bareback horse race that’s been held there since 1644. 

• Palazzo Pubblico: Siena’s city hall since medieval times and the current home of the Civic Museum. Many of its rooms are covered in frescoes, including the famous “Allegory and Effects of Good and Bad Government” series (1338-1339) by Ambrogio Lorenzetti.

• Torre del Mangia: Italy’s third-tallest tower is attached to the Palazzo Pubblico. You can climb 87 meters to the top for sweeping views of the rest of the city and the surrounding hills.

• Cathedral of Santa Maria Assunta: This Romanesque-Gothic cathedral features early sculptures by Michelangelo. The ornate marble mosaic floor, with designs by about 40 Sienese Renaissance artists, is fully visible for a few months each year, from mid-August to October.

• Bottini: Siena’s ancient aqueduct system, over 25 kilometers long, still feeds the city’s historic springs. Visitors can take a guided tour through this underground labyrinth.

Once an important stop for pilgrims heading from France to Rome, San Gimignano is a 13th-century hill town that’s on the UNESCO World Heritage List. Its medieval towers have earned it the nickname “the Manhattan of the Middle Ages,” with 14 of an original 72 still standing. You can climb Torre Grossa, the tallest tower, for views of the town and rolling hills. You may recognize another tower, the Devil’s Tower, from the video game Assassin’s Creed. 

Volterra, a hilltop village in the province of Pisa, has a 3,000-year history spanning Etruscan, Roman and medieval times. Each period has left its mark. Here are just a few of the historical highlights:

• Porta all’Arco: Porta all’Arco is the only remaining gate of the Etruscan city wall that was built in the 4th and 3rd centuries BC. Some believe the three weather-worn heads that adorn its arch are gods; others think they’re vampires.

• Guarnacci Etruscan Museum: One of the oldest public museums in Europe, this museum showcases a wealth of Etruscan and Roman artifacts collected by Italian abbot and historian Mario Guarnacci. Don’t miss the mysterious Etruscan sculptural masterpiece “Shadow of the Evening.” 

• Roman Theatre Complex: The Vallebuono archaeological area features the remains of a well-preserved Roman theater, built at the end of the 1st century, as well as a spa complex and an Etruscan acropolis. A recently discovered amphitheater is still being excavated.

• Palazzo dei Priori: This, Tuscany’s oldest civic building, has a bell tower that offers a great view of the city and beyond.

A hillside town in the Valdichiana area, Cortona was made famous by the 2003 film “Under the Tuscan Sun.” But its roots go back a lot farther: According to legend, Cortona was founded by a descendant of Noah (of the Ark fame) about 270 years after the Great Flood. 

Cortona’s steep, narrow alleys connect bustling piazze, historic palazzos, artisan boutiques and authentic Tuscan trattorias. Check out artifacts from Etruscan tombs and even an Egyptian burial boat from 2000 B.C. at the Etruscan Museum. Soak in the silence at the mystical Franciscan monastery Le Celle Hermitage. Enjoy the view from the top of the Girifalco Castle tower.

For those who crave deeper insight into the region’s culture and traditions, there are still more ways to experience Tuscany. Here are some suggestions to get you started: 

• Cooking classes: No matter where you go in Tuscany or how much time you have, you’ll find many opportunities to learn how to make the local dishes. Some classes boast well-known chefs or tutors; others have amazing views while you work. You could look for how to make pasta, bread or pecorino cheese. There are even classes that’ll teach you how to cook like a Tuscan nonna.

• Harvest events: The annual grape harvest, which takes place all over Tuscany between late summer and early autumn, draws big crowds. But it’s not the only regional harvest event. For example, Volterra hosts the White Truffle Festival in October. Also in October, look out for one of the many festivals celebrating chestnuts. And in May, Lari celebrates its native cherry varieties, and Terricciola celebrates strawberries.  

• Thermal spa retreats: Tuscany is rich in thermal spas and hot springs. Many are near Monte Amiata, a dormant volcano in the south. Depending on your preference, you could take the waters at a luxurious wellness resort or a rustic open-air spring. Some of the most famous spa towns include Chianciano, just below the Val d’Orcia; Saturnia in the Maremma region; Montecatini Terme in Pistoia; and Petriolo, between Monticiano and Civitella Paganico.

No trip to Tuscany would feel complete without a visit to Florence, the region’s capital city. Brimming with Renaissance art and architecture, it’s also a major food, shopping and fashion destination. Here are just some of the tastes, products and sights that Florence is particularly well known for.

Florentine food often emphasizes fresh, seasonal and local ingredients and embraces the cucina povera (poor food) philosophy you can find throughout Tuscany. Some specialties of Florence include:

• Lampredotto: A street-food sandwich made from part of a cow’s stomach that’s slowly cooked in a broth of herbs and tomatoes.

• Ribollita: A soup of greens, cannellini beans, vegetables and stale bread to thicken it.

• Bistecca alla Fiorentina: T-bone steak from premium local beef cooked over a wood or charcoal fire and seasoned simply. 

• Schiacciata con l’uva: Oven-baked flatbread stuffed with grapes.

• Trippa alla Fiorentina: Tripe simmered in tomato sauce and sold at “tripe stands” around the city.

Leathermaking in Florence dates back as far as Etruscan times. The industry really took off in the 13th century, and today the Florentine leather industry is world-renowned. Many local artisans use a leatherworking technique that originated in Florence: the ancient Cuoietto Artistico Fiorentino—a completely handmade process, from cutting and shaping to dyeing and finishing. 

Visitors can immerse themselves in this rich tradition by exploring the sprawling Mercato Centrale and the lively San Lorenzo Market for an array of leather goods, from everyday accessories to luxury items. You can also watch the meticulous handcrafting process at a local artisan workshop or browse elegant boutiques for high-end Florentine leather creations. Keep in mind that at markets like these, cash may be preferred, prices may be negotiable and imitations still exist.

The city, widely believed to be the birthplace of the Renaissance, is home to many museums and masterpieces of art and literature. Here are a few of Florence’s can’t-miss cultural highlights:

• Galleria degli Uffizi: Botticelli’s “Birth of Venus” and “La Primavera,” Caravaggio’s “Medusa,” Titian’s “Venus of Urbino,” Leonardo da Vinci’s “Annunciation” and Raphael’s “Madonna del Cardellino”… the Uffizi Gallery has some of the most famous works of art in the world. The gallery’s focus is on the Renaissance, but the art spans from ancient Greece to the 18th century.

• Palazzo Pitti: Across the Ponte Vecchio from the Uffizi Gallery, you’ll find the Palazzo Pitti, a complex of four separate museums showcasing everything from precious objects to Russian icons to Renaissance and modern art to fashion. The complex also includes the elegant Boboli Gardens.

• Piazza del Duomo: Cathedral Square is at the heart of Florence’s historic center and is bordered by some of the city’s most famous monuments: the Cathedral complex of Santa Maria del Fiore, including the cathedral, the dome, the bell tower and the baptistery; the Opera del Duomo Museum and more. 

• Galleria dell’Accademia: A short walk from Piazza San Marco, you’ll find the Gallery of the Academy. It holds the largest number of Michelangelo sculptures anywhere, including the world-famous masterpiece “David.”

• Museo Nazionale del Bargello: The oldest public building in Florence, the Palazzo del Bargello was once the residence of the city’s police chief and later a prison. It then became Italy’s first national museum and now houses the city’s most important collection of Renaissance sculpture. Look out for works by Donatello, Michelangelo, Cellini and many more.

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From food and wine to scenery and history, Tuscany offers a little of everything you might expect from a classic Italian vacation. This guide can hopefully help you zero in on the perfect Tuscany experience for you. 

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