Wine, gelato, picturesque vistas…more wine. Tuscany, the region in central Italy surrounding Florence, is undeniably a bucket-list destination thanks to its delicious cuisine, historical sites and charming villages. It’s glorious any time of year, although fall tends to be less crowded, with an almost endless list of things to do. Need some help making plans? Here are 50 of the best things in Tuscany to add to your itinerary.
The 50 Best Things to Do in Tuscany
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Published Sep 20, 2018
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1. Kick things off by ascending the iconic Leaning Tower of Pisa. The 14th-century bell tower may be askew, but it still offers sweeping views of the surrounding town and countryside. Love sticking to a schedule? Reserve tickets in advance online.
2. Don’t forget to visit the Museum of Human Anatomy, also in Pisa, which collects mummies, skeletons and wax models.
3. Need to raise your step count? Take a jaunt, or a leisurely bike ride, around the greenery-covered city walls of Lucca, which encircle the old city for four kilometers.
4. If you get hungry after your walk around Lucca, stop by Buccellato Taddeucci, a bakery that sells the city’s famed sweet bread buccellato (among other delicious items).
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5. Visit the Piazza del Campo, Siena’s sprawling and historic central square. It’s the perfect base from which to explore the medieval town or simply sit and watch the passersby with an espresso.
6. While in Siena, climb up the Torre del Mangia, a 14th-century bell tower (there are lots of them in Italy) with views of the town and the Tuscan hills.
7. Or, uncover your own cooking skills at Tuscan Women Cook, a cooking school in the stone, hilltop village of Montefollonico with weekly classes led by skilled local chefs.
8. Detour through Arezzo, which is home to the ancient Anfiteatro Romano, the remains of a Roman amphitheater built in the first century AD.
9. History buffs will also appreciate Arezzo’s Medici Fortress, constructed back in 1500 by the Medici family. It features a public park, which is ideal for walking off lunch.
10. Indulge in a wine tasting at Enoteca la Fortezza, located in an old fortress in Montalcino, an area that’s famous for Brunello reds.
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11. In Florence, explore the Boboli Gardens, a beautiful collection of gardens that date back as far as the 15th century, where every hidden corner unearths another impressive sight.
12. Step inside the massive Florence Cathedral, with its arching red-roof Duomo, to uncover intricate artworks. You can even climb to the top of Brunelleschi's cupola for aerial views of the city.
13. Marvel at the vast displays of Renaissance art in Florence’s renowned Uffizi Gallery, a sprawling art museum filled with masterpiece after masterpiece you’ll more than likely recall from your history books.
14. For an unforgettable Instagram story, hop over to the Accademia Gallery, which houses Michelangelo’s David, among other famous works. (Although, you might have to be super sneaky about snapping a photo.)
15. Want something off the beaten track? Head to the eclectic Il Giardino dei Tarocchi, or “Tarot Garden,” a collection of colorful, whimsical outdoor sculptures created by Niki de Saint Phalle.
16. Prefer your art for free? Spend every first Sunday of the month museum hopping as part of #DomenicalMuseo, during which numerous spots, including the Palazzo Pitti’s Modern Art Gallery, are gratis for visitors.
17. For a quiet afternoon with a book, hunker down at Biblioteca delle Oblate, which boasts a terrace café with a view of Florence’s Duomo.
18. Did you know gelato originates from Florence? Celebrate that newfound knowledge with a scoop (or two) at Vivoli, which has been around since 1930.
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19. Even more famous is Gelateria Dondoli, located in San Gimignano. The shop is highly acclaimed and well worth the journey (and gelato lovers of all ages can even partake in the Dondoli Gelato Class).
20. Save up your pennies and book a table at Enoteca Pinchiorri, Tuscany’s sole three-Michelin starred restaurant (we were surprised, too), where guests can experience innovative dishes that focus on a balance between past and present.
21. For a quick bite to eat, pop into Florence’s hole-in-the-wall eatery Salumeria Verdi (also known as Pino’s Sandwiches), where you can order a perfect, gooey panini.
22. If you’re after piles of fresh produce, pay a visit to one of Tuscany’s many outdoor markets, which include Florence’s Mercato di Sant'Ambrogio and Mercato Centrale (which also serves up prepared dishes and glasses of wine).
23. Go even deeper into the local wine culture on a day-long winery tour around Chianti. Try the highly-rated Chianti Wine Tour, which departs from Florence and includes a stop in San Gimignano.
24. If you’d rather stay close to the city, sip an Aperol Spritz (or something stronger) on the rooftop terrace of Florence’s La Terrazza Lounge Bar, which offers sweeping views of the city and the Arno River.
25. For something even more indulgent, try your hand at truffle hunting with The Truffle Hunter, where you can search out the prized culinary treat. Spoiler alert: An adorable dog is involved.
26. Bring an empty bottle to fill up on your choice of homemade (!) wine for only a few euros at Divino Di Sara Vestri (Via Taddea, 6).
27. If beer is more your speed, head out to the town of San Quirico d'Orcia, where visitors can discover a small craft brewery called Birrificio S. Quirico.
28. Tuscany isn’t just known for its booze: Embark on an olive oil tasting tour with Arianna & Friends and learn about traditional oil mills and sample some of the local wares.
29. When you’re ready to leave the cities, uncover a hidden gem by traversing the Vie Cave, a collection of old Etruscan roads located near Sorano.
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30. About an hour’s drive north, visitors can splash around in the natural outdoor hot springs in Bagni San Filippo, which can be reached via a quick walk through the nearby woods (BYO towel).
31. For a more luxurious hot springs experience, unwind at the Terme di Saturnia, a spa and resort with thermal pools, a golf course and top-of-the-line treatments.
32. Further north, venture inside the Grotta del Vento (“Cave of the Wind”), located in Garfagnana and open most days of the year for guided treks into the caverns.
33. Garfagnana is also home to the small lakeside village of Isola Santa, a ghost town that dates back to the Middle Ages. Although it’s largely abandoned, a few low-key holiday homes are now open, including Borgo Isola Santa.
34. To fully enjoy the Tuscan sun, rent a bicycle and cycle the “Renaissance Ring,” a 172-kilometer path that rolls through the hills and countryside outside Florence, stopping many iconic sites along the way. To keep it simple, book a private guide with Florence Bike Tours.
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35. Speaking of the sunshine, for a special occasion, book a stay at the Villa Bramasole, the idyllic country home from Under the Tuscan Sun.
36. Those especially obsessed with Diane Lane’s journey to find herself in Under the Tuscan Sun should also stop by Cortona, the hilltop village from the film that boasts nice shopping, eateries and sublime views.
37. It’s not just for aspiring divorcees: Cortona hosts an international photography exhibition, “Cortona On The Move,” each year from July through September, perfect for travelers shopping for inspiration or simply some new wall décor.
38. Visitors often forget that Tuscany includes beachfront destinations, including Elba (where Napoleon was exiled), an island in the Tyrrhenian Sea that boasts well-known stretches of sand and waves. Opt for a small family-run B&B rather than a resort hotel.
39. When you get tired of the beach, head to Elba’s Mount Capanne, which can be summited by hiking or hopping in the terrifyingly amazing cable car.
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40. To fully explore the Tuscan coastline set sail on a mini-cruise with Montecristo Sailing, which visits Elba, as well as the islands of Giannutri and Giglio.
41. No trip to Tuscany is complete without at least one night in a real-life castle. Castello di Vicarello, a luxury hotel that welcomes guests in all seasons, will tick that fairy-tale box, and then some.
42. If budget is more your speed, head to the countryside near Siena to book one of the chic tents at The Lazy Olive Glamping.
43. Those who covet Italian designers like Gucci, Ferragamo and Cavalli should dedicate an entire day to The Mall, a collection of luxury outlets in Florence that boasts deep discounts.
44. Serious shoppers can even visit the factory outlets for Dolce & Gabbana, Fendi and Prada while in Tuscany, several of which are located adjacent to The Mall.
45. For something more unique, search out one of the recurring antique markets, which include Florence’s Mercato delle Pulci and Arezzo’s Fiera Antiquaria.
Taverna del Percorino
46. Go all in and purchase some acclaimed Pecorino cheese to take home while in Tuscany. The best spot: La Taverna del Pecorino in Pienza, which also sells wines, olive oils and other artisanal products.
47. Take your sweetheart to score some good luck at the gold Tree of Love in the Museo di Lucignano the small Medieval town of Lucignano.
48. Lovers can also pay a visit to Florence’s Ponte Vecchio, an iconic bridge that arcs over the Arno River, where couples often clip on padlocks and throw away the keys to symbolize eternal love.
49. Speaking of romance, grab a table at Florence’s beloved family-run restaurant Trattoria Sabatino, which boasts incredibly low prices and home-style Italian dishes.
50. End your Tuscan holiday with a farewell cruise through the countryside in a vintage Fiat 500 with 500 Touring Club, which even offers a sunset wine tasting tour.