14 Unforgettable Things to Do in Tuscany

Written by Rem Malloy, since 1995 Rem has been guiding and designing trips to Italy and all of Western Europe and is considered an expert in his field for over 30 years.

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Nestled along Italy’s dreamy west coast, Tuscany is one of the most popular regions to visit in Italy. Between idyllic rolling hills, stunning vineyards and ancient medieval villages, it is no wonder that this haven has proved such a hit amongst visitors. 

With jaw-droppingly gorgeous landscapes and rich cultural, artistic and historic legacies, there is so much to do and see in the region. So, we have collated a list of the 14 most unforgettable things to do in Tuscany to help you plan the most wonderful trip possible to this gorgeous pocket of paradise.

1. Wander the Streets of San Gimignano

A romantic hilltop town that simply exudes romance, the streets of San Gimignano offer all the quintessential charm you’re craving from Italy at a convenient distance from the region’s capital of Florence. Also known as Delle Belle Torri, the town boasts a captivating skyline of medieval towers.


There are so many things to see in San Gimignano. From world-famous vineyards and medieval fortifications to the brilliant San Gimignano Museum and Duomo di San Gimignano, you will not find yourself short on things to do in this ancient metropolis.

2. Discover the Vineyards in Tuscany with a Chianti Wine Tasting

Chianti is one of the most famous regions in the world for wine and if you want to truly taste it at its best, you need to visit the vineyards of Tuscany. 

A real paradise for wine lovers, picture yourself strolling along the rolling landscapes, sipping exquisite grape juice all the while learning about its history and production. A vineyard tour is definitely one of the best things to do in Tuscany.

Wine Festivals

With wine being an integral part of Tuscan culture, the region plays host to several fantastic wine events throughout the year that you’ll want to have on your radar.

Cantine Aperte

Taking place in May, Cantine Aperte is the perfect event for wine fans. Meaning ‘open doors’ in Italian, wine cellars open their doors to the public during this festival, inviting them in to explore the property, sample the wine and learn all about its production.

While many vineyards in Tuscany welcome visitors all year round, some only do so during Cantine Aperte so this is a pretty exciting time for wine enthusiasts. Locals and tourists come together to get a unique look into the behind-the-scenes action of some of the region’s most exclusive vineyards.

Mostra Del Chianti

Mostra Del Chianti is one of Tuscany’s most popular wine festivals. Taking place in Chianti, the event lasts several days between the end of May and the beginning of June. 

Expect to be treated to live music, street shows, theater performances, parades and reenactments in what is sure to be fun for all the family. Guests will also be able to enjoy delicious food samplings with Chianti pairings during this wonderful celebration of culture, history and heritage.

Vendemmia Wine Harvest

The Vendemmia, or, Wine Harvest, takes place between mid to late September and is a highly celebrated event in the Tuscan countryside. This is the best time to go on an agro-tour in Italy as you can get an up-close look at the intricate work that goes behind selecting grapes and fermentation.

You’ll be able to find many of these tours around Tuscany, many of which are run by wineries and B&Bs. As wine is such a major part of life in Italy, this is the perfect way to embrace the culture around you.

3. Get Lost in Florence 

Visiting Florence is a must for those on their holidays in Tuscany. As Italy’s first capital city, it is drenched in culture, history, art and, naturally, a world-class food scene. Stroll along the beautiful streets, admiring the medieval buildings around you before wandering into a divine eatery. 

Renowned for its unrivaled array of museums, you will want to dedicate a significant portion of your time to investigate all they have to offer. Another of the top things to do in Tuscany is climbing Il Duomo di Firenze. This will treat you to jaw-dropping views over the city.

4. See the Leaning Tower of Pisa

Seeing the Leaning Tower of Pisa is hands down one of the most unique and unusual things to do in Tuscany. Known in Italian as Torre Pendente di Pisa, this iconic landmark tilts at an angle of 4 degrees, appearing as if it is constantly teetering upon the edge of destruction. 

Fear not, this UNESCO World Heritage Site has been around since the late 12th century and doesn’t seem to be going anywhere anytime soon! Do not miss out on the chance to visit this famed piece of architecture.

After snapping an iconic photo in front of the landmark, take some time to explore the surrounding area. There are plenty of pizza shops that make wonderful places to stop in for a bite to eat.

5. Hit the Hot Springs

Fortunately for you, Tuscany is certainly not in short supply of spa towns with an abundance of incredible natural hot springs in the area. Visiting these natural jacuzzis is one of the most wonderful free things to do in Tuscany.

Relax and unwind in perfectly hot water amidst the gorgeous Tuscan countryside. One thing to bear in mind is that you should wear older bathing suits to this attraction, as the sulfur smell can be rather potent and may linger on your clothes!

Saturnia is one of the most sought-after hot springs in the area, with its eye-catching turquoise waters and stunning tiers. On the other hand, Bagno Vignoni is another fantastic option in a tiny village just south of Siena. No matter where you head, prepare to enjoy the utmost tranquility in nature’s very own bubble baths.

6. Visit Siena National Gallery

While Italy is famous for being home to outstanding museums, the Siena National Gallery is easily one of its best. Located in what was once a 15th-century palace, it is home to a spectacular collection of Sienese art. 

Dander around gorgeous paintings, sculptures, manuscripts, drawings and ceramics with highlights including the works of Matteo di Giovanni, Benvenuto di Giovanni and Francesco di Giorgio.

7. Go Truffle Tasting in San Gimignano 

One of the top things to do in Tuscany is going truffle tasting in San Gimignano. There are few experiences more unique than spending your day hunting for truffles with a canine companion in the enchanting Tuscan forests.

What’s more, hunting for the most delicious edible treasure has to be the ultimate foodie activity. 

Key Event: White Truffle Festival

Taking place in November, the White Truffle Festival is one of Tuscany’s largest extravaganzas. Celebrating white truffles, it’s located in San Miniato and offers an exciting opportunity for visitors to have a stab at truffle hunting, take home truffle-based products and sample dishes made from, you guessed it, truffles.

8. Visit the Basilica of Santa Maria Assunta

As one of the most incredible and highly renowned pieces of Gothic architecture in the whole of Italy, the Cathedral of Santa Maria Assunta is nothing short of breathtaking. So, it may come as no surprise that paying a visit to this iconic landmark is one of the most fantastic things to do in Tuscany.

Located on the island of Torcello, Venice, prepare to be blown away by the grand design of the Late Paleochristian architecture before venturing into the building’s equally impressive interior. 

9. Explore the Ancient Hill Towns

Tuscany is blessed with an abundance of dreamy villages nestled into its rolling hills. These little havens make wonderful places to explore, especially the town of Cortona on the southern slope of Sant’Egidio Hill.

This stunning hilltop paradise shot to fame in 2003 following its cameo on ‘Under the Tuscan Sun’. It’s no wonder why it proved so noteworthy amongst the location scouts, as it boasts jaw-dropping views over the surrounding countryside and an exquisite food scene.

10. Take a Tuscan Food Tour

As one of the most iconic foodie destinations in the world, one of the must-do things in Tuscany is taking a local food tour. It is a great idea to do this towards the beginning of your holiday so you can discover your favorite dishes early on and make the most of them during your trip. 

Key Events

Sagra Food Festivals

Sagra food festivals are local events that take place during the fall in celebration of local food and drinks. Sit elbow to elbow with residents, tasting their finest traditional dishes surrounded by a buzzing atmosphere. 

The events also tend to feature special menus, tastings, demonstrations, and competitions. While most remain rather under-the-radar, some have gained international recognition in recent years such as the Sagra della Castagna in Soriano nel Cimino where you can try phenomenal beef stew and roasted chestnuts.

11. Visit Uffizi Gallery

Try your best to squeeze in a visit to the Uffizi Gallery in Florence – you won’t regret it! Boasting some of the finest art in the country, the three-tiered gallery offers an abundance of incredible exhibitions to see during your visit.

Some of the finest work includes Botticelli’s Birth of Venus. Spending the afternoon meandering around these iconic works is one of the most fascinating things to do in Tuscany.

12. Eat Gelato

Gelato is a delicious Italian delicacy that is said to have been invented in the Tuscan capital of Florence. So, where better to indulge in this scrumptious treat than in its birthplace? You will find a whole host of wonderful gelaterias throughout the region.

In fact, there is no better way to recuperate from the arduous work of sightseeing than by people watching in a piazza with a refreshing cone of gelato. Pistachio, chocolate, espresso – whatever the flavor, this is one of the finest ways to spend an afternoon in Tuscany.

13. Walk Along the Ancient City Walls in Lucca

The idyllic Tuscan city of Lucca is a treat for the eye to see between its gorgeous Romanesque buildings and distinctive white and yellow houses. It is truly one of the most beautiful towns in Tuscany

It would be a crime to visit this little paradise without visiting its captivating city walls. These beautiful fortifications boast stunning views over the city and make incredible places to explore, especially for those looking for things to do in Tuscany with family. You can choose to tour the four-kilometer circuit by foot or bicycle if you’re looking to add an extra layer of excitement. 

14. Take a Cooking Class

As such an iconic foodie destination, you’ll definitely want to take a cooking class during your time in Tuscany. These are exceedingly popular throughout the region so you shouldn’t struggle to find one at a convenient location.

Mastering classic Italian dishes such as pasta, pizza and risotto is possibly the best souvenir that you could bring back to friends and family. They’ll be reaping the benefits for years to come!

Summary

Visiting Tuscany is sure to be a magical experience no matter when and where you go. From an excellent food and wine scene to rich cultural and historical heritage and a wealth of breathtaking landscapes, the region really does have it all. 

With so many things to see and do in Tuscany, it is worth getting clued up on the most unforgettable things to add to your bucket list so you can plan the most unforgettable trip possible to this romantic paradise.

Fancy cycling through the dreamy Tuscan landscapes or being guided through the region’s highlights by a local expert? Italy4Real provides a range of small group tours of Tuscany that offer the perfect way to explore this stunning part of the world.

About the Author

Rem Malloy started Italy4real back in 1995 with his mother, Deborah de Maio.

He specialises in Italian tours as well as customised tours to France, England, Ireland, Germany, Switzerland, Greece and Spain. He was also featured in the Travel Channel show Mysteries at The Museum in 2016.

Rem has family in Italy and his mothers home town is Cava di Terrani, near the Amalfi Coast. The family has a street named after them in Sorrento, Via Luigi de Maio; a relative who was mayor of Sorrento.

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