A Complete Guide to the Best Things to Do in Tuscany

Tuscany. Just saying the word evokes images of sun-drenched hills, medieval towns, olive groves, and rows of cypress trees leading to charming stone farmhouses. This central Italian region is a dream for travelers who love history, culture, food, wine, and nature. Whether you’re sipping Chianti in a hilltop vineyard, admiring Renaissance masterpieces, or exploring quiet backroads, Tuscany offers unforgettable experiences for every type of traveler.

I’ve explored Tuscany more than once, each time, discovering something new and magical. Whether you’re planning your first trip or returning for a deeper dive, this guide will help you uncover the best things to do in Tuscany, including must-see cities, hidden hill towns, food and wine adventures, and more.

Explore Tuscany’s Historic Cities

1. Florence (Firenze)

No trip to Tuscany is complete without a stop in Florence, the beating heart of the Renaissance. It’s a city where every corner seems to hide a masterpiece, whether it’s an ornate church façade, a marble statue, or a hidden fresco in a side chapel.

Highlights include:

The Uffizi Gallery – Home to Botticelli’s The Birth of Venus and countless Renaissance treasures. You can book skip-the-line tickets and tours to make the most of your visit.
The Accademia Gallery – Where you’ll find Michelangelo’s David in all its marble glory.
The Duomo (Santa Maria del Fiore) – Climb Brunelleschi’s dome for one of the most breathtaking views of the city.
Ponte Vecchio – The iconic medieval bridge lined with jewelry shops, perfect for a sunset stroll.

Tip: Florence can get overwhelming with crowds, especially in summer. If you can, explore early in the morning or later in the evening. Wandering the narrow streets when they’re quiet is pure magic. For a convenient stay, find hotels near the Duomo on Expedia.

2. Siena

Siena is like stepping back into the Middle Ages. Its brick buildings, winding streets, and Gothic architecture give it a distinct character compared to Florence. The city’s centerpiece, Piazza del Campo, is one of the most beautiful squares in Europe, shaped like a shell and lined with cafés.

If you’re visiting in July or August, you might catch Il Palio, Siena’s famous horse race, a centuries-old tradition that’s part competition, part pageantry, and entirely thrilling. Make sure to book accommodations in advance in Siena during this time, as the city fills quickly.

3. Pisa

Most people come to Pisa for one thing: the Leaning Tower. And yes, it’s as delightfully crooked in person as it looks in the photos. But don’t stop there. Pisa is home to an entire architectural complex known as the Piazza dei Miracoli (Square of Miracles), including the stunning cathedral and baptistery.

Once you’ve ticked the tower off your list, head into the old town. The Arno River winds through Pisa, and its riverside walkways are filled with trattorias and lively student crowds. To save time, consider a Pisa half-day tour with tower tickets.

4. Lucca

Encircled by intact Renaissance walls, Lucca is a city made for strolling. You can actually walk or cycle along the top of the walls, which are now a leafy promenade offering views of both the old town and the surrounding countryside.

Inside the walls, you’ll find charming piazzas, Romanesque churches, and narrow lanes that beg to be explored. Lucca also has a strong music heritage. It’s the birthplace of composer Giacomo Puccini, and you can even attend an opera performance in his honor.

5. Arezzo

Arezzo is one of Tuscany’s underrated gems. Known for its antique fairs and artisan workshops, it’s less crowded than Florence or Siena but equally rich in history. The city was also the filming location for parts of Life is Beautiful, and you’ll see familiar scenes as you wander.

Don’t miss:

Piazza Grande – a sloping square surrounded by medieval architecture.
Basilica of San Francesco – home to Piero della Francesca’s famous fresco cycle, The Legend of the True Cross.

Discover Hilltop Towns & Villages

Tuscany’s smaller towns and villages are just as captivating as its cities. Sometimes even more so. These are places where time seems to slow, where sunsets paint the stone walls gold, and where life is savored at a different pace.

6. San Gimignano

Known as the “Medieval Manhattan,” San Gimignano is famous for its medieval towers that still punctuate the skyline. Walking through its cobbled streets feels like a journey back in time. Be sure to try a scoop of gelato from Gelateria Dondoli, often voted among the best in the world.

For an authentic experience, try a wine-tasting tour in San Gimignano.

7. Montepulciano

This hilltop town is a wine lover’s dream, best known for its Vino Nobile di Montepulciano. The town itself is a maze of Renaissance palaces, charming squares, and wine cellars where you can sample local vintages. Stay in a vineyard agriturismo nearby for a true Tuscan countryside experience.

8. Cortona

Perched high above the Val di Chiana, Cortona has breathtaking views and a laid-back atmosphere. It became especially famous after the book and film Under the Tuscan Sun. Beyond the movie connection, it offers Etruscan history, cozy cafés, and warm Tuscan hospitality.

You can book a guided walking tour of Cortona to uncover its fascinating past.

9. Volterra

Volterra is often quieter than its neighbors but no less fascinating. It has deep Etruscan roots, medieval fortifications, and alabaster workshops where artisans still handcraft beautiful pieces. If you enjoy history without the crowds, Volterra is a must.

10. Cultural & Artistic Experiences

Museums & Galleries

Uffizi Gallery (Florence) – Botticelli, Leonardo da Vinci, Caravaggio.
Accademia Gallery (Florence) – Michelangelo’s David.
Siena’s Pinacoteca Nazionale – Gothic art from Siena’s golden age.

Theaters, Opera & Artisan Workshops

Tuscany thrives on creativity. You’ll find opera houses, small theaters hosting local performances, and artisan workshops where traditions like leatherworking, ceramics, and paper marbling are still alive. Watching a craftsman at work can be as moving as seeing a Renaissance masterpiece.

11. Food & Wine Experiences

Food in Tuscany is about simplicity and flavor. Every dish tells a story of the land.

Classic Tuscan Dishes

Ribollita – A hearty vegetable and bread soup.
Pappa al Pomodoro – Tomato and bread soup, rich and comforting.
Bistecca alla Fiorentina – A massive T-bone steak grilled over wood fire.
Cantucci with Vin Santo – Almond biscuits dipped in sweet dessert wine.

Wine Regions

Chianti – Rolling vineyards between Florence and Siena. Join a Chianti wine-tasting tour.
Montalcino – Famous for Brunello di Montalcino, one of Italy’s greatest wines.
Montepulciano – Known for Vino Nobile di Montepulciano.

Olive Oil & Truffles

Tuscany produces some of Italy’s finest olive oil. Tastings are common, and you’ll quickly learn why fresh, peppery Tuscan oil is so prized. In autumn, join a truffle hunt in San Miniato, where trained dogs sniff out these culinary treasures.

Cooking Classes

Few experiences are as memorable as joining a local family for a cooking class. From rolling fresh pasta to making tiramisu, you’ll take home more than recipes. You’ll take home stories. You can book authentic Tuscan cooking classes through Viator.

12. Outdoor Adventures & Scenic Landscapes

Chianti Countryside

Cycle or drive through vineyards, stopping at wineries and small villages along the way. Try a bike tour through Chianti.

Val d’Orcia

A UNESCO World Heritage site, the Val d’Orcia is the Tuscany of postcards. Rolling hills, cypress-lined roads, and golden fields. Stay in a charming farmhouse hotel in the Val d’Orcia. Towns like Pienza and Montalcino add charm to the scenery.

Hiking in the Apuan Alps & Apennines

For those who love the outdoors, Tuscany offers rugged mountain hikes with panoramic views.

Hot Springs & Spas

Saturnia – Natural hot springs with cascading pools. Many resorts can be found on Expedia.
Bagno Vignoni – A thermal village where the main square is a hot spring pool.

13. Coastal Escapes & Islands

Versilia Beaches

Forte dei Marmi and Viareggio are popular with stylish Italians in summer.

Maremma

Less touristy, with wild beaches and rugged coastline.

Elba Island

Napoleon was exiled here, but today it’s loved for its beaches, hiking trails, and laid-back charm.

14. Road Trips & Scenic Drives

Renting a car unlocks Tuscany’s true magic.

Chianti Wine Country – Rolling hills and vineyard stops.
Val d’Orcia Drive – Pienza, Montalcino, Montepulciano.
Sunflower Season – In summer, the countryside glows yellow.

15. Shopping & Local Crafts

Tuscany is famous for leather goods, ceramics, alabaster, and artisanal jewelry. Florence’s San Lorenzo Market is a great starting point, but many small towns also specialize in local crafts.

Practical Tips for Visitors

Best Time to Visit – Spring (April–June) and fall (September–October).
Getting Around – Trains connect cities, but rent a car to explore villages.
Language – Basic Italian phrases go a long way.
Budgeting – Tuscany can be pricey, but local trattorias offer great value.

Hidden Gems & Off-the-Beaten Path

Pitigliano – Known as “Little Jerusalem” for its Jewish heritage.
Massa Marittima – A medieval town with fewer crowds.
The Crete Senesi – A surreal, lunar-like landscape near Siena.

Conclusion

Tuscany is more than a destination. It’s a state of mind. It blends history, culture, landscapes, and gastronomy in a way few other places can. Whether you’re gazing at Renaissance art in Florence, sipping Brunello in Montalcino, or watching the sunset over a sunflower field, Tuscany invites you to slow down and savor.

So, if you’ve been dreaming of that perfect Italian adventure, let this be your sign: it’s time to plan your trip to Tuscany. Start by finding the perfect place to stay and add unforgettable experiences with tours and activities. Trust me, once you go, you’ll want to return again and again.

Enjoy this blog? Please spread the word :)

We may earn from qualifying purchases from Amazon. Learn more here.