15 unforgettable things to do in Tuscany

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Rough Guides Editors
1/13/2021

Tuscany harbours the classic landscapes of Italy, familiar from a thousand Renaissance paintings, with its backdrop of medieval hill-towns, rows of cypresses, vineyards and olive groves, and artfully sited villas and farmhouses. It’s a stereotype that has long held an irresistible attraction. Nowadays Tuscany is among Italy's wealthiest regions, but it remains predominantly rural, with great tracts of land still looking much as they did half a millennium ago.

It’s not possible to see everything that Tuscany has to offer in one trip – but this selection of the region's highlights is a great place to start. From our Rough Guide to Tuscany and Umbria, this is our pick of the best things to do in Tuscany.

1. Taste truffles in San Miniato

Tuscany offers plenty of opportunities for sampling this perfumed and pricey fungus. San Miniato, a brisk little agricultural town more or less equidistant between Pisa and Florence, is particularly renowned throughout Italy for its variety.

To get to know the town, take a guided walk with an English-speaking guide to discover the squares, palaces, and cathedrals.

2. Take a day-trip to Cortona

The ancient hill-town of Cortona is the major attraction on the agricultural plain of the Valdichiana, its steep streets giving an unforgettable view over Lago Trasimeno and the Valdichiana. In the wake of the film of Under the Tuscan Sun, Cortona was briefly the second most popular Italian destination for US tourists after Venice, but although it still attracts busloads of tourists nowadays, its steep little streets have not yet lost their charm.

A private, English-speaking tour guide can help you discover the best parts of the city while explaining the most important historical and artistic beauties.

View of Cortona in Tuscany - shutterstock

3. Go wild in the Monti dell’Uccellina

The protected environment of the Monti dell’Uccellina is one of Italy’s last pristine stretches of coastline. The Maremma region in which it lies was long Tuscany’s forgotten corner, its coastal plains, marshes, forest-covered hills and wild, empty upland interior having been a place of exile and fear for much of the last five hundred years, but in this regional park efforts have been made to preserve these natural treasures.

4. Make a pilgrimage to La Verna

St Francis’s mountaintop retreat, still a thriving Franciscan monastery commanding wonderful views of the Apennines, is Tuscany’s major pilgrimage site. Some come here to pay homage, others to stay in the guesthouse adjoining the monks’ quarters and some merely out of curiosity. Unlike at the basilica at Assisi, however, sightseers rarely obscure the purpose of the place.

If you're planning a day trip to La Verna then a private car and driver will be the most comfortable method of transportation. You can even book a separate guide with your transport.

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5. Get lost in The Uffizi, Florence

The Uffizi, Italy’s finest collection of art and the world’s greatest collection of Italian Renaissance paintings in Florence has recently doubled in size. There are so many masterpieces collected here that you can only skate over the surface in a single visit – set aside at least half a day to explore. Make sure to book ahead so you can skip the line and spend more time exploring the museum. Besides visiting the Uffizi, Florence as one of the most beautiful cities in the world is easily worth a multi-day stay.

The beautiful building housing the Uffizi in Florence, Tuscany - shutterstock

6. Go walking in the Alpi Apuane

Famous for their marble quarries, the Alpi Apuane of Northern Tuscany are also something of a botanical wonderland, with vast forests of beech and chestnut, and a profusion of wildflowers in spring. A network of clearly marked footpaths and longer trails thread the steep forested valleys, and there are some three hundred species of birds to spot as you hike – including the golden eagle, kestrels, buzzards and sparrowhawks.

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7. Visit the Piero della Francesca masterpieces in Arezzo

Exquisite Renaissance works adorn almost every place of any size in Tuscany, but the stunning fresco cycles in Arezzo by Piero della Francesca are some of the finest of the region’s riches. Only 25 people are allowed into the choir of San Francesco at a time, so to be sure of getting in at the hour you want, check the Rough Guide for details of how to book a place in advance.

Arezzo itself with its picturesque historic centre is worth exploring further. Discover the square that appeared in 'La vita è bella', Roberto Benigni's most famous film, further on to the cathedral and the different churches. A private, English-speaking guide is the best option to learn more about the history and culture.

8. Wander the streets of San Gimignano

San Gimignano – “delle Belle Torri” – is famed for its amazing skyline which is dominated by fifteen medieval towers. The beautifully preserved streets are a vision of medieval perfection, making it one of the most beautiful places in Italy. Try to visit out of season if you can though, the town's magic can be compromised in summer by huge numbers of day-trippers.

One of the most wonderful experiences in San Gimignano is accompanying an expert and his dogs on a truffle hunt. Learn how to recognise and search for truffles in a stunning private oak forest, before enjoying an authentic Tuscan lunch.

San Gimignano

9. Be a tourist in Pisa

It might be the subject of millions of postcards, but the Campo dei Miracoli in Pisa is still worth visiting. There's a breathtaking array of buildings here: the Leaning Tower, Italy’s signature building saved from collapse in the nick of time, the vast Romanesque cathedral, the magnificent baptistery and the Camposanto with its beautiful frescoes and impressive tombs.

It pays off to book ahead, as both the cathedral and the Leaning Tower can get crowded.

10. Walk the city walls in Lucca

Lucca has some of the most handsome Romanesque buildings in Europe, but tourism here is very much a secondary consideration. Get to know the town by walking (for example with this guided walking tour) or cycling the fortifications that still completely encircle the old city – the mid-afternoon shutdown is perhaps the best time to follow the 4km circuit, which is lined with plane, lime, ilex and chestnut trees.

11. Wine down in Chianti

Some of Italy’s finest vintages are produced in these celebrated vineyards between Florence and Siena. The region can seem like a place where every aspect of life is in perfect balance: the undulating landscape is harmoniously varied; the climate for most of the year is balmy; and on top of all this there’s some serious wine tasting to get stuck into...

If you're staying in Florence, there are many different day tours to choose from, our favourite includes a visit to two different wineries.

12. Embrace open-air art

Located 5km southeast of Capalbio is one of Italy’s oddest collections of modern art, Il Giardino dei Tarocchi (Tarot Garden), a whimsical sculpture garden of prodigious works by Niki de Saint Phalle. The brightly coloured, Gaudí-esque opus took the artist almost seventeen years to complete and the result is a truly staggering sight – sheer fun that children love and adults marvel at.

13. Sample island life on Giglio

Out in the Tuscan archipelago, Giglio is relatively unspoilt by the sort of tourist development that has infiltrated – though certainly not ruined – nearby Elba. This little jewel of an island boasts citadels, stone villages and panoramic mountain hikes, as well as beaches and watersports.

14. Hit the spa

Tuscany has some of the swankiest spa towns in all of Italy, but at Bagno Vignoni in Southern Tuscany you can soak without paying a cent. This tiny and atmospheric village has a wonderful natural hot spring and Medici-era pool in place of a central piazza – sadly this is now out of bounds, but you can take a dip in the free outdoor sulphur pools nearby.

15. Go rural

Staying in Tuscany's hill-towns obviously makes sightseeing easier, but the quality and variety of the region’s rural accommodation is outstanding. If you want to splash out, try a top-price hotel in a sublime setting such as the Castello di Velona. This twelfth-century “castle” 10km south of Montalcino is now a superb 46-room five-star hotel, set in lovely open countryside on its own hill and ringed by cypresses.

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