The 11 best things to do in Tuscany

One of Tuscany's main draws is that it has something for every type of traveller and, in fact, you can create a fully rounded itinerary even if you only have a few days.

Here is our guide to the best things to do in the region, from biking down classic country roads to truffle hunting in the woods, to scoring an antique heirloom, or blending your wine like a Renaissance man, plus insider tips on where to find the best tomato, or fresco.

For further inspiration, see our guide to Tuscany and its best hotels, restaurants, beaches and drives.

Modern architecture is not something you see often in Italy, particularly in Tuscany, which makes Antinori nel Chianti Classico, a new showcase for Antinori’s vintages, even more groundbreaking. A visionary soaring complex of steel and light, it calls to mind Richard Serra’s sculptures. Situated outside the town of Bargiano, about 20 minutes' drive from Florence, the showstopper was designed by architectural firm, Archea. Inside the structure, which took seven years to design and construct, the layout is a mixture of cantina, bar, restaurant and museum, all dedicated to the famous Antinori wines. 

Insider tip: To taste a number of vintages rather than choosing a bottle, sample a flight of the label’s range at the property’s tasting room.

Contact: antinori.it
Price: ££

Podere Il Casale, an organic farm close to Montepulciano and Pienza, exemplifies Tuscany’s zero-mile approach to food (getting ingredients from home, or as close to home, as possible). The property, owned by a Swiss family who fell in love with Italy, has a hippie bohemian feel as peacocks and sheep wander about and volunteers help out, sleeping in campers at night. Come to see how they make cheese and then sit down to sample their sustainable and seasonal menu. 

Insider tip: Be sure to pick up a jar of their homemade honey too.

Contact: podereilcasale.com
Price: ££

This prized ingredient is one of Tuscany’s and Italy’s most famous products, a kind of foodie couture. Sniffed out by dogs or pigs, the best of them sell for exorbitant prices internationally but here you can get them for a fraction of the price. Even more fun is to set up a truffle hunting tour that finishes with you sampling your own truffle with a plate of local pasta. The hunters and their dogs who accompany you seem right out of central casting. Book your hunt with a good outfitter such as Select Italy or Truffle Hunter. 

Insider tip: You can find black truffles here much of the year but for the prized white variety book your trip for October or November.

All over Italy the concept of the local festa (festival) thrives and Tuscany is no exception. Most visitors to the region will be familiar with Siena’s Palio, the twice-a-summer bareback horse race that pits contrada (neighborhood) against contrada, in a most medieval way. But it’s only one of the spectacles on offer. In Montepulciano at the Botte di Bravio, two men roll 50kg barrels up the city’s twisted streets in a way that makes Crossfit look wimpy. Meanwhile in Pienza at the Fiera del Cacio, teams of children and adults put a new spin on bowling, spinning pecorino cheese in circles in the town’s main square.

Insider tip: Join a neighborhood dinner after the competition, there are usually a few tickets on hand for non residents.

Going to see how wine is made and the estates that turn out the best vintages has to be one of Tuscany’s main pleasures. The properties range from more professional tours (there is often a restaurant on site too) to small family producers where a call in advance to see if they are open is a must (your hotel should be able to set up a tour at most estates). Among the vineyards to consider: Avignonesi is one of Montepulciano’s most famous producers for its Vino Nobile wine, which can be sampled at the property’s excellent restaurant. At Montalcino’s Casanova di Neri, a Brunello maker that has scored consistently in the high 90s in Wine Spectator, the tasting room can popped into without an appointment. 

Insider tip: Make time for smaller family operations too. Ask a local for their favorite low-key producer and where you can try a hand at blending.

Bagno Vignoni has long been on travelers’ radars for good reason. In the Middle Ages, it was a stop along the Via Francigena, the route that took pilgrims from Rome to France, and in this little town they found natural thermal springs to ease their muscles. Today, after exploring the thermal waters – either at the free springs just out of town or at a hotel like Il Albergo Posta Marcucci – visitors can head to the speakeasy Il Barriano a watering hole with elixirs so balanced and unusual even the monks would have been impressed. At the bar’s helm is Bledi Ndoci, an Albanese mixologist who came to Italy as a child and moved to the Val d’Orcia recently —try the Mais Amor with Tequila, Mezcal, Elicriso, corn, lime, and ginger salt. 

Insider tip: Heading into the Christmas holidays Bagno Vignoni is particularly delightful with its lit-up tree on the water and the mist coming off the central square in a ridiculously romantic way.

Contact: facebook.com/ilbarrinobagnovignoni/
Price: £

Even though Tuscany is most highly rated for its eating and drinking, sporty types will find lots to entertain and challenge thanks to the notoriously hilly landscape. Cycling is a favorite diversion here with outfitters such as Duvine and Backroads specialising in tours through the region (one also can easily rent a bike for the day too and the proliferation of ebikes has made those epic hills a bit more manageable). Hikers will find paradise here too; there are hundreds of unpaved roads here called white roads that lead between towns and beautiful abbeys. Meanwhile if a Vespa is more your speed rent one through a company such as Tuscany by Vespa.

Insider tip: Before your trip pick up a copy of Walking and Eating in Tuscany and Umbria – the authors suggest excellent walks that end with a great meal (try Montalcino to the Abbey of San’t Antimo).

One of the growing trends all over the country, from food producers to clothing designers, is to keep products as sustainable as possible, and made with quality ingredients, or textiles. The thinking is that with this kind of emphasis Italian labels will continue to be one of the greatest offering on the global market. Of course, this philosophy has been around for centuries. In Anghiari, for example, the showstopping linens and table wear at Busatti have been made on looms here since 1842. At Tenuta di Spannocchia, a farm and castle that’s been around since 1225, extra virgin olive oil and multi-floral honey are only some of the organic and biodynamic products they make and sell on site. 

Insider tip: If you stay at a property like Tenuta di Spannocchia you can also learn about other projects like the raising of Tuscan farm animals, which were on the verge of going extinct. 

While many of the weekly markets have started selling as many cheap clothes as heirloom tomatoes, there are still some atmospheric and authentic options. One of the best has to be Greve in Chianti’s Il Pagliaio, held every fourth Sunday of the month, March through December. Everything on sale is organic and you can find seasonal gems such as Porcini mushrooms or melt in your mouth figs.

Other exceptional markets include Livorno’s Il Mercato Centrale, where a vast complex of stalls is housed in an impressive 19th-century building – not surprising considering the city’s location on the coast, the seafood choices are excellent. And Carrara, known for its beautiful white marble, also has a famous market, the Mercato delle Erbe, held every Saturday morning, and highly rated for its organic focus.

Insider tip: If antiques are more your passion, make tracks to Arrezzo, which takes place the first weekend of the month. Candlesticks and jewellery are only a few of the finds to put in your suitcase. 

Capalbio, a lovely town close to the sea, has long been the preferred second home choice for noble Romans and the society set. Its beautiful beaches and easy proximity to the Eternal City, make it a popular choice for short breaks, but there’s a less well-known attraction that’s more than worth a stop. The town’s ‘Tarot Garden’ – Il Giardino dei Tarocchi – is home to a series of sculptures by Niki de Saint Phalle (she envisioned her creation in a dream while she was shut up in an asylum). These 12-15 meter high sculptures scattered through a 14-acre garden atop Etruscan ruins are made from mosaics and are one of the most famous works by the artist. The surreal kaleidoscope renditions represent each card of the tarot deck – a sphinx, for example, comes with mirrored blue hair and a red crown, one breast covered by a flower and the other by a purple heart. 

Insider Tip: Sample the Italians take on glamping nearby with a stay at the lodges of Terra di Sacra in a WWF refuge and close to chic beach clubs like La Dogana. 

Contact: ilgiardinodeitarocchi.it
Price: £

Illy is a world-renowned name in the coffee universe, but less well known is the family’s foray into the wine world at the spectacular Podere ai Ripi vineyard outside of Brunello-famous Montalcino. Biodynamic and organic, the wine has quickly risen to award-winning status thanks to the loving attention of owner Francesco Illy and his main oenologist, Sebastian Nasello. The unusual circular cantina known as the “golden cellar” is state-of-the-art, and we love the wines’ names like Amore e Magia (love and magic), Amore e Follia (love and folly,) and Lupi e Sirene (wolves and mermaids). One of the best aspects of the property is how child-friendly it is: instead of waiting impatiently for parents to finish their seemingly endless tastings, children can gather eggs, pet the donkeys and other animals like the beautiful Chianina cattle, and dress up like a farmer while learning about the property’s eco-sustainable garden. 

Insider tip: Before or after your vineyard visit head to the 12th century abbey of Sant’ Antimo, one of the most beautiful structures in all of Tuscany. 

Contact: podereleripi.com
Price: ££