31 Hidden Gems in Tuscany – How to Get Off the Beaten Path

You are here Home > Destinations > Italy > 31 Hidden Gems in Tuscany – How to Get Off the Beaten Path

Explore these hidden gems in Tuscany and leave the crowds behind. Find secret spots, alternative places and get off the beaten path in Tuscany with this inside guide.

Unusual thing to do in Tuscany - agroturismo honey post

Find Unusual Things to do in Tuscany​​​​​ with these Hidden Gems

Tuscany has plenty upon plenty of things to do, that’s for sure. With no fewer than seven UNESCO World Heritage Sites, the claim as the birthplace of the Italian Renaissance, the Leaning Tower of Pisa and more, it’s no surprise that Tuscany remains one of the most popular places to visit in Italy, if not the world.

And yet. Stunning though these places are, it does mean that some of the off the beaten track things do get overlooked. Experiences that would top the list in lesser-endowed places fall through the travel guidebook cracks in luscious Toscana.

Well, not any more!

Behold, dear readers, let me clue you in to off the beaten path things to do in this part of Italy with these hidden gems in Tuscany.

Recommended reading: unusual things to do in Italy

Disclosure: if you book or buy through any of the links on this page, we may earn a small commission at no extra cost to you. Cheers!


I love sharing the best travel resources I can find. 

Tuscany Off the Beaten Path

The unusual Vespa Museum

Visit the Vespa Museum

The Vespa museum in Pontedera, Tuscany, welcomes you not with racy Vespas and photos of celebrities, nor dashing ad campaigns. Those wait inside. Instead there’s a memorial and a polished aerobatic trainer plane, monuments to the man who began his career in aeronautical engineering but who achieved fame with a much smaller machine: the Vespa. It’s one of the best hidden gems in Tuscany.

On the one hand there’s the breathless icon, the vision of beautiful Italian limbs perched upon beautiful Italian design, zipping past fountains, ochre walls and cafes practically swaying with romantic intrigue. On the other, there’s a bald man in a shirt and tie. The man who designed the thing.

That man was Corradino d’Ascanio.

Inventing the Vespa

Piaggio hired d’Ascanio, they both got to work and after a few shiny prototypes, the Vespa was born. Its unique design had gears on the handlebars, a single metal chassis and an easy way for riders to rest their feet on the platform instead of straddling an unwieldy mechanical beast.

Splash guards even protected those tailored Italian suits.

Either from the Vespa’s narrow waist or from the buzzing of the engine, the motorbike reminded both men of a wasp. This was handy, since Vespa in English means wasp.

Fame and Hollywood followed, surpassed only by a visit from the British Blue Peter team.* The Vespa became both a legend and an art form and the museum in Pontedera celebrates it well.

Yet the words on the plaque by the exit are the ones that stay with me still:

“Corradino d’Ascanio, 1891 – 1981

A man of science and extraordinary imagination and creativity.

The book of his life tells the story of aviation, the helicopter and the Vespa.”

The museum also shows glamorous photos of a woman with long hair clasping the man of her dreams as they speed through the Tuscan countryside.

Behind every sexy invention, you’ll find an engineer.

Unusual thing to do in Tuscany - take a cooking lesson

Take An Authentic Cooking Lesson in Tuscany

“This is the classic ragù that my grandmother taught me: a delicious, versatile sauce that can be used in many ways. Added to lasagne, any type of pasta, served with meatballs…” Lella from Cuoche in Vacanza

It’s no secret that Italians like their food. And one of the best hidden gems in Tuscany is having a secret cooking lesson so that you can bring the flavours of the region back home.

I loved the in house cooking course with Cuoche in Vacanza. They come to your self catered accommodation or villa and teach you all the tricks of the trade.

Find the recipe for the real ragu and the details for the cooking lesson over here. 

Unusual thing to do in Tuscany - take a vow of silence_

Wander the Charterhouse of Calci

In unmarked graves, the Charterhouse monks of Calci used death to extend their earthly vows of silence into eternity.

While the brothers ran the pharmacy, the fathers lived reclusive lives, speaking only once a year and passing food between walled tunnels to avoid the temptation for a chat.

Yet despite this severity, austerity never really caught on.

The Charterhouse notches up an impressive 1500 rooms, plus a view of the leaning tower of Pisa on that infamous clear day. Living quarters come with private orchards, while cloisters overlook fountains and a gated panorama of Tuscany at its best.

In fact, it’s this very richness that’s the real curse in this part of Tuscany. With the splendours of Florence and Pisa nearby, little attention remains for buildings that would otherwise be protected, promoted and thriving.

Like the others, the Charterhouse is struggling. The last monks left in the 1970s, leaving the cloisters crumbling behind them.

Part of me wonders whether this is how things need to be. That it’s impossible to restore and remember everything and that in trying to do so we risk losing today’s resources.

But then another part recognises this as one of Tuscany’s hidden gems. And hopes that it survives.

Unusual thing to do in Tuscany - look for ghosts

Find a laughing ghost

Agustino Agustini greets guestsin the hallway of Villa di Corliano, a house, no make that a mansion, complete with a driveway that sweeps through the grounds like a flourish from a period drama. Florentine eagles flit across the vault, while whispers of ghosts hide behind chandeliers.

You can stay here, in this lovingly restored unusual piece of history. But you have to be able to handle the ghost. 

Unusual things to do in Tuscany - bird watching

Go Bird-watching at Massaciuccoli

Bring your binoculars and drink in the soothing silence of sunset. Look out for kingfishers and ducks amid the swaying reeds above and crayfish and eels below. Find out more about walking in Massaciuccoli here.

Unusual thing to do in Tuscany - flowers near Lucca

Take a Road Trip Through Tuscany

Embrace the freedom of the wide open road and those lines and lines of cypress trees by finding your own way through Tuscany. That way, you can hit the main sights of Florence or Pisa and then take in these unusual spots plus discover a few more surprises of your own.

Recommended – Road Trip Essentials: How to plan the perfect road trip anywhere in the world.

Unusual thing to do in Tuscany - agroturismo

Visit an Agroturismo Farm

Indulge in homemade jams, honey, extra virgin olive oil and a meal made from vegetables grown in the very same garden. All while taking in views of the Serchio River. Spazzamento calls this agriturismo. I call it simple pleasure.

Find out more about the Agriturismo Spazzamento here.

Meet the Gloom of the Nicosia Monastery

Beneath the arches, a cloaked man walks through the shadows, his head bent, his hands supporting an open book. I can hear my footsteps, distorted through the darkness by the basement’s wet gravel, a hesitant chord to the beat of dripping water.

Upstairs, in the clouded daylight, it’s easier to see the wooden planks covering the windows and the words that scream “take my blood.” It’s also easier to see the table decked with homemade olive oil, bread and wine.

This is the Nicosia Monastery, a place that chalked up nearly 800 years of active service before the last few monks hung up their cassocks in the 1970s and the vandals moved in. Among the ripped plaster and violent graffiti, a neatened orange grove provides fragrance and a sense of peace.

It’s being painstakingly restored by the Nicosia Nostra, a volunteer organisation founded in 2004 from people in the neighbourhood who wante to save the place. They host outdoor concerts in summer, construct nativities in winter, and spend the rest of the year lurking in basements to scare the bejesus out of visiting writers.

Talk about Tuscany’s hidden gems.

Hidden gems in Tuscany Italy

FAQs about Tuscany Hidden Gems

You asked, I answered! Here’s more about Tuscany off the beaten track.

What is Tuscany known for?

Tuscany is known for rolling hills, olive groves, medieval towns and great food. The region has a huge artistic and historic legacy, as both the birthplace of the Renaissance and the home of the modern Italian language. It’s also a popular holiday spot, with cities like Florence, Siena, Lucca, Pisa, San Gimignano, Montepulciano and more.

What are some non-touristy things to do in Tuscany?

Beyond the secret spots in Tuscany mentioned higher up, some non touristy things to do in Tuscany include the following:

  • Catching the sunset views at Pitigliano.
  • The Saturnia Hot Springs.
  • The natural thermal baths at Bagni San Filippo.
  • Porto Santo Stefano – a beautiful coastal town.
  • Giglio Island – a gorgeous spot within the Toscano National Park.
  • Lajatico – the hometown of one Andrea Bocelli.
  • Val D’Orcia for those iconic countryside views.
  • San Gimignano – popular hill town with towers to climb.

Where in Tuscany has the most beautiful rolling hills?

The region of Val D’Orcia is probably the most famous part of Tuscany, with those rolling hills and upright trees.

Where to stay in Tuscany off the beaten path?

You will find so many gorgeous places to stay in Tuscany off the beaten path. I’d highly recommend the places recommended in this article on hidden gems in Tuscany. Namely: Villa Corliano.

What is the most beautiful part of Tuscany?

Well, beauty is in the eye of the beholder, of course. But it’s hard to beat the rolling hills of Val D’Orcia.

Read more about Italy with these travel tips

2 thoughts on “31 Hidden Gems in Tuscany – How to Get Off the Beaten Path”

Leave a comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.