The 35 best things to do in Tuscany, Italy

Tuscany in Italy is synonymous with rolling hills, beautiful landscapes, romantic, medieval hill-top towns, delicious Italian cuisine, a fantastic selection of wines, and a rich (art) history & culture. When planning your trip to this beautiful area it is not always easy to narrow down the bucket list, as there are more things to do and see than could possibly fit into one single trip. In this post, you can be inspired by the 35 best things to do in Tuscany, Italy to help you plan your adventure. From nature, outdoor activities, culture & museums to romantic city-getaways and culinary delights, this post has you covered!

Having lived in Italy for four years brought me to Tuscany several times. The below list is non-exhaustive but provides a good mix of must-sees as well as some activities or sights off the beaten path and insider tips for culinary and outdoor adventures. Without further ado: here are the 35 best things to do in Tuscany!

1. Check out Florence’s famous Duomo

At the center of Florence lies Piazza del Duomo, its centerpiece being the Florence Cathedral. Begun in 1296 the Cathedral is one of Italy’s largest churches and still remains the largest brick dome ever built. Its sheer size is overwhelming, as is the beautiful marble facade in various shades of green, pink, white, and black. Inside the cathedral, you will find beautiful Renaissance art – especially the interior of the dome is well worth seeing.

Next to the Cathedral are the Baptistry as well as the Campanile (Belltower), built by Giotto. All three buildings together are a UNESCO World Heritage site and one of Tuscany’s prime tourist attractions. As with many tourist attractions in Italy, you will need a ticket to visit all three sites. I recommend you get these online – they cost around €25 per ticket.

2. Admire marvelous Renaissance Art af the Uffizi Galleries

The Uffizi Gallery is without doubt one of the most famous art collections in the world, boasting a plethora of sculptures and famous paintings from ancient to modern times. Even if you are not a great fan of museums, the Uffizi is special in its own right, as the building itself is already worth seeing. Spread over two stories, the Gallery contains some very famous artworks such as “Spring” or “The Birth of Venus” by Botticelli, sketches by Da Vinci, or paintings by Raphael or Perugino.

My tip: After finishing the first story, have a glass of Prosecco at the rooftop Bistro, with a nice view over Florence’s rooftops and a chance to rest your feet before hitting the ground floor.

For culture lovers, there are many more fantastic Galleries & sights to see, such as the Accademia, Palazzo Strozzi, Palazzo Pitti, or the Boboli Gardens. The latter two, together with the Vasari Corridor can be visited in a combined ticket to the Uffizi.

If you want to have full freedom and visit most of these Museums in any case, you could consider buying the “Firenze Ticket” for €85, allowing entrance to Florence’s main sites within 72 hours. This post by VisitFlorence.com gives a nice overview of the pros and cons of getting the card.

3. Watch the sunset over Florence from Piazzale Michelangelo

There is no better way to end a long day in Florence than to watch the sun set slowly over the rooftops and surrounding hills from Piazzale Michelangelo. Get a bottle of wine or some beers, and some snacks and end the day admiring the beauty of one of Italy’s most famous cities.

To get to Piazzale Michelangelo either take the Bus Lines 12 or 13, walk (1,9km ~30 minutes) or drive there. Parking is available on the square (but may get full in the evening time).

4. Stroll over Ponte Vecchio and (window-)shop handmade jewelry

One of Florence’s most famous landmarks is “Ponte Vecchio” or Old Bridge, crossing the Arno river running through Florence. It is a medieval stone bridge dating back to Roman times, with buildings on top of the bridge on both sides. On top of the buildings runs the famous Vasari Corridor, connecting Palazzo Pitti to Palazzo Vecchio.

Centuries ago the bridge was occupied by butchers, tanners, and farmers. Today it is home to high-end luxury jewelers, art dealers, and souvenir stores.

5. Eat yourself through Mercato Centrale, Florence

Mercato Centrale is within walking distance of the Duomo and is a destination well worth visiting if you want to explore off the beaten path. The Mercato Centrale, located in the historic building of Mercato San Lorenzo, spans over two floors.

On the first floor, you will find a traditional food market with local produce, fruit, veggies, cheese, meats, etc. On the top floor is a sort of food court with various local specialties. Grab a glass of wine and some Antipasti or other food, and have a nice “Aperitivo” with the locals to soak up the vibes.

On their website, you can find more information about current events & themed weeks.

6. Try out “Pici” Pasta with “Ragu”

Italy and pasta are a match made in heaven. Everybody knows Spaghetti, but have you tried Tuscany’s own pasta type “Pici” yet? They are thicker than spaghetti, often hand-rolled by artisans, and taste especially delicious with “Ragu” sauce (Bolognese or meat sauce) or with a creamy, truffle sauce. Must-try!

You can get Pici in local supermarkets, they make a nice culinary souvenir for family or friends back home.

7. Stay at an “Agriturismo” in the Tuscan countryside

Agriturismo refers to accommodation at locally, still operational farms or producing businesses usually in the agricultural sector. In Tuscany terms, this usually refers to staying in a Bed and Breakfast situated on a local wine farm, or a farm producing things such as cheese, honey, or olive oil.

You can find agriturismi all over in Tuscany, and they make for a very nice, down-to-earth option to stay, with a very local feel. Often at Agriturismi, the family tells you about their operations, invites you to taste local delicacies such as homemade wine, cheeses, or cold cuts, and can give you wonderful tips on things to do in the area. A big plus: you usually have more space than at a hotel and they usually come with beautiful gardens, where you are free to roam around.

We stayed at two agriturismi while in Tuscany: at Agriturismo Podere Giardino in Monteaperti (at cottage Capanna) and at Cretaiole, just outside of Pienza. Monteaparti is just outside Siena, so a perfect base for exploring the various cities around Tuscany as well as the Chianti wine region. Cretaiole is right near Pienza, so also a perfect home base for exploring around the Montalcino, Pienza, Montepulciano area.

8. Take a roadtrip to the many fortified hilltop towns (Volterra – San Gimignano – Colle di Val d’Elsa – Monteriggioni)

No Tuscany road trip would be complete without visiting the many fortified hilltop towns scattered all over the region. Therefore, one of the best things to do is to take a road trip to the likes of San Gimignano, Colle di Val d’Elsa or Monteriggioni.

Winding roads, beautiful vistas on the surrounding hills, cute souvenir stores, and restaurants with food to die for. All towns have these points in common. However, each town has its very own feel to it, so it is worth visiting as many of them as possible.

Your best option for town-hopping around Tuscany is by car (ideally a small car to make parking easier) or you can even do this with a Vespa or motorino (scooter) to get the full Italian experience.

9. Admire the medieval “Skyline” of San Gimignano

San Gimignano is on top of the to-do list of any trip in Tuscany. What makes San Gimignano so special is that it personifies Tuscany all in one town. Embedded in rolling hills, surrounded by vineyards, and with its intact old city center, the town became a UNESCO world heritage site in the 90s.

Surrounded by a fortified wall from the 11th century, it exudes a medieval charm with an Italian twist. Also nicknamed the “Manhattan of Tuscany”, San Gimignano’s “Skyline” is characterized by several towers overlooking the city. In medieval times, these towers were seen as a status symbol and built by wealthy families in a “race” who could build the tallest tower. In the 14th century, the city boasted around 70 towers. Of these, only 13 remain today.

In addition to its architectural spectacle, San Gimignano also offers several very cute souvenir stores, wineries, and the self-proclaimed best Gelateria in the world.

For wine lovers: don’t miss out on trying the locally-grown Vernaccia di San Gimignano wine with its D.O.C.G. label since 1993.

10. Shop artisan handicraft souvenirs

In Tuscany, you will find many family-run, handicraft stores where you can get legitimate, locally-made souvenirs such as pottery, textiles, or culinary delights (wine, cheese, cold-cuts, honey, etc.). I recommend getting souvenirs from local artisans rather than from very touristy souvenir stores, as these support the local artisans, allowing them to keep practicing their handicraft, often passed on from generation to generation.

Often you can also witness the artisans making your piece directly in front of you, which adds to the memory associated with each piece.

11. Go on a bike tour through the Chianti wine region

There are few ways to better explore Chianti – one of Italy’s most famous wine regions – than on a bike. If you have a good fitness level, you can go by regular bike; alternatively, I recommend going by e-bike as the area is quite hilly.

Our bike tour took us on about 37 km through beautiful landscapes, by cypress-lined hills, cute hilltop towns, and by several wineries. We started out in Monteaperti, just outside of Siena, and took the following route:

• Monteaperti
• Castelnuova Berardenga
• San Gusmé
• Castello di Brolio
• San Felice
• Castello di Bossi
• San Piero
• Monteaperti

The whole tour took about 3 hours (not including our stops to check out San Gusmé & two wine tastings at Castello di Brolio & Castello di Bossi) and was about 530 meters elevation gain over the tour.

If you are traveling by e-bike, you can easily extend the tour by circling by Lecchi in Chianti or the Chianti Sculpture Park.

Make sure you take enough water with you as well as some snacks. Depending on the season & day of the week/time of day, there may be no stores open in the little towns on the way.

12. Taste the famous “Chianti Classico” red wine at its birthplace Castello di Brolio

As you can probably tell from this post, I am a wine lover, so on our trips, we never miss out on a chance to taste the local wines.

Chianti is a wine region in Italy that produces mostly red wines. A very nice place to do a wine tasting is at the Enoteca of Castello di Brolio, “the birthplace of Chianti Classico”. (If you like culture, you can take a guided tour of the Castle and its gardens and do a wine tasting afterward.)

Chianti DOCG wine and Chianti Classico DOCG are two distinct subtypes of Chianti wines, as Chianti Classico has stricter guidelines (e.g. minimum 80% Sangiovese grapes, no addition of white grapes allowed, etc.).

There are three different types of Chianti Classico that you can taste – a simple Chianti Classico (minimum aging of 1 year), a Chianti Reserva (at least 2 years aging), and Gran Selezione (at least 3 years of aging).

13. Visit the beautiful Duomo di Siena

Siena has got to be one of the most beautiful towns in Tuscany and is a long-term rival of Florence. And one thing to definitely not miss out on during your visit should be the Duomo di Siena – the famous Siena Cathedral, completed in 1264. Situated in the city center, its facade and interior are completely out of white & green-black marble. Some of the most renowned artists of the era such as Pisano, Donatello, or Bernini worked on pieces found in the cathedral.

The inside of the cathedral is just as fascinating as its outside: the entire floor is covered in 56 marble mosaics of the finest handicraft from about 40 different artists.

Adjoining the cathedral is the Piccolomini Library, which is also well worth seeing with its display of old, hand-painted choir books, frescoes, and paintings depicting the life of Enea Silvio Piccolomini, one of Siena’s most famous citizens who eventually became Pope Pius II. We will see more of him later in this post 😉

14. Have an “Aperitivo” at Piazza del Campo, Siena

Piazza del Campo is Siena’s main square in the old city center, surrounded on all sides by beautiful buildings & facades. There is no better way to take in all the details of the square, than by sitting in one of the numerous cafés or bars and enjoying an Aperitivo with some snacks and just watching the action and bustling unfold.

15. Explore Siena’s “Contrade”, dating back to the Medieval times

Siena is not only a really beautiful city. It has a very interesting history as well. One of the most unique things about it is probably the history of its 17 “contrade” or city districts. If you pay attention, you will find little symbols on the streets, showcasing which Contrada you are in right now.

The contrade were set up in the Middle Ages and represented different military camps that fought to maintain Siena’s independence from Florence. Nowadays the military aspect is long gone, but the contrade stayed and represent important cultural identities of its inhabitants – a sort of local patriotism.

Each Contrada has its own symbol, history, church, museum, fountain, motto etc. Most important events in daily life (e.g. baptisms, marriages) are celebrated within a Contrada.

16. In summer: visit the unique “Palio di Siena”, the most famous horse race in the world

The annual, world-famous Palio di Siena horse race, which takes place twice a year on July 2nd & August 16th, is the culmination of Siena’s contrade tradition, in which a jockey from each Contrada competes against the others. The race takes place on the central Piazza del Campo and is definitely a one-of-a-kind spectacle.

If you get the chance to visit Siena during this time, you will be able to experience a unique cultural gem, dating back to the Middle Ages.

17. Have (lots of) Italian gelato

A must-do during your stay in Tuscany: have a delicious original, Italian gelato or ice cream. Several gelaterias (ice cream parlors) claim to be “the best Gelateria” in the world (notably two alone in San Gimignano city center). The only way to know for sure is to try it out 😉

18. Enjoy a 4-course Truffle dinner, cooked by “Mamma”

Tuscany is a region well-known for its truffles. There are several activities tied to this delicacy – such as truffle hunting with a “truffle hunter” and his truffle dog (often a Lagotto Romagnolo), specially trained for the task. You can go on truffle tastings, buy them at several souvenir stores to cook yourself at home.

Insider Tip: have a delicious 4-course Truffle dinner at “Il Tartufaio” in Monti in the Chianti area. Giorgio is the owner, host, waiter, cook, and truffle hunter and creates a very warm and intimate atmosphere. Make sure to reserve a table, as there are only about 5-6 tables in the small, family-run space. For €40 you will get Antipasti, Primo (first main – usually pasta), Secondo (second main – usually meat), and dessert. Additionally, as much wine and water as you can drink to accompany the dinner and of course “vin santo” a dessert wine locally from Tuscany. A very authentic experience, far away from very touristy places.

19. Take your perfect Tuscany photo at “Il Baccoleno” (43°12’03.4″N 11°35’23.7″E)

A winding alley of cypress trees, romantically situated among rolling, green hills? Yes, that is the Tuscany most people imagine. There are many places where you can find a constellation of these, but the classic, famous picture spot can be found at the geographical coordinates above, which are at the Agriturismo “Il Baccoleno“.

There is no specified parking spot, as it is not actually a “sight”. It is actually the driveway to an agriturismo (where you can stay overnight). To get there, you can just simply pull up at the side of the road. Other cars will probably be there too, so make sure you slow down before pulling over, or you may miss the spot.

20. Visit the beautiful monastery of “Abbazia di Monte Oliveto Maggiore”

Nested in between hills lies the hidden gem of the monastery of Monte Oliveto Maggiore (founded in 1319). The medieval palace in red brick is surrounded by a large garden with a cypress alley and a cistern from 1533. The cloister is filled with beautiful medieval frescoes by Signorelli and Sodoma from 1497-1505 depicting the life of St. Benedict. In the upstairs part of the abbey, you will find a library and pharmacy, both worth visiting as well.

Somewhat off-the-beaten-path the abbey is well worth a small detour on your Tuscany trip and can easily be visited by car.

21. Take a photo at picture-perfect “Cappella di Vitaleta”

Another famous photo spot in Tuscany is surely Cappella di Vitaleta, located off the road between San Quirico d’Orcia and Pienza. The chapel, located in the middle of a breathtaking landscape, was built in 1553 and is part of the UNESCO World Heritage list.

It is also the perfect spot for a romantic picnic. So pack a blanket, a bottle of wine, some local Pienza cheese, and a fresh loaf of Ciabatta and spend a chilled afternoon in this beautiful spot, where time seems to standstill.

22. Rent a Vespa and take a ride through the Tuscan hills and vineyards

Ever wanted to ride a Vespa? Well, your holiday in Tuscany is probably the perfect time & place to do it. You can rent a Vespa in the larger cities such as Siena or Florence or from local providers in smaller towns. The cost varies from provider to provider, but you will need to calculate somewhere around €60-€75 for a day.

Alternatively, you can also book a guided tour on Vespa through Tuscany with a fixed itinerary and usually including one Vespa per 2 persons.

23. Visit natural hot springs

The ancient Romans already knew about the healing qualities of the thermal hot springs in Tuscany. Here, hot sulfurous water at 37°C gushes from the rock and over waterfalls down into natural pools.

There are several of these that you can visit: Saturnia (the most famous) or Bagni San Filippo. In these towns, you will find a few high-end Spa Hotels or baths, as well as publicly accessible hot springs directly in nature. The reviews about Saturnia and Bagni San Filippo are very mixed and depend on your own subjective adventurer spirit.

Tip: The best time to visit the hot springs is around sunrise during the week. Avoid public holidays or weekends. It gets extremely crowded (even at sunrise) and unfortunately looks nothing like the beautiful pictures you see online.

24. See the leaning tower of Pisa at Piazza dei Miracoli

When you think of Pisa, you will probably think of the leaning tower in the same train of thought. But on Piazza dei Miracoli (in English “the square of miracles”), there is much more to be seen.

The whole square is a UNESCO World Heritage site, and home to four beautiful monuments: the Pisa Cathedral, the Pisa Baptistry, the Campanile (Belltower – the famous leaning tower), and the Monumental Cemetery.

So take your time, soak in the fantastic views and see all there is to be seen on this beautiful spot.

25. Go on a hike through the beautiful Val d’Orcia

The landscapes of Val d’Orcia are a masterpiece of Medieval landscaping and are some of the most picturesque in the world. A good way to explore it is by foot on a hike connecting the different towns.

One thing to be mentioned: Italy (except for the mountainous North) is not the most hiking-friendly destination, as trails are often not marked and sometimes hard to follow. My suggestion is to follow an app such as Komoot or other outdoor apps and plan your trip ahead / follow an itinerary.

Our hike (see Komoot link) took us from Agriturismo Cretaiole over Bagno Vignoni (& Parco dei Mulini), Vignoni Alto over the ancient Via Francigena to San Quirico d’Orcia and back over Cappella della Vitaleta to Cretaiole. It was a nice tour, albeit quite long, with about 20km but some stuning views along the way and many points of interest.

So if you enjoy the outdoors and nature, hiking is a great way to explore!

26. Visit the ancient Roman Bagno Vignoni

Since Roman times (and earlier even the Etruscans), the small town of Bagno Vignoni was known for its hot springs. In the center of the village is a large square filled with water, the “square of sources”, containing the volcanic thermal water coming from the underground spring. It is a very unique site and I recommend you stop by to check it out.

A small way out from the central square, you will find the “Parco dei Mulini” where you can see the old aqueducts leading the spring water to the main square and the water connecting over a set of terraces.

27. Explore Lucca with its intact Renaissance-era city walls

If you plan to travel closer to the Ligurian coast, you should not miss Lucca in your itinerary. Famous for its Renaissance-era intact city walls, Lucca is a beautiful example of a typical, Tuscan medieval town.

While there, you should not miss out on climbing the famous Torre Guinigi, from where you have a fantastic view of the city. Stroll around the narrow streets of the old town, visit the San Michele Church, the Dome of San Martino, Church San Frediano, and Piazza Anfiteatro – a city square built entirely on the foundations of an ancient Amphitheater.

If you are mobile (car, bike, etc.), I recommend you do not miss out on visiting the impressive bridge “Ponte della Maddalena“. It crosses the Serchio river and is located just outside of Lucca near Borgo a Mozzano. It is also known as the “Devil’s bridge”, which can be traced back to various legends.

In the most common tale, the bridge builder was upset about not finishing the bridge according to the deadline. That night the devil appeared and promised him to finish the bridge in exchange for the soul of the first person to cross the bridge. With the devil’s help, the bridge was finished that same night. However, the witty bridge builder decided to send a pig over the bridge first, to protect the souls of the town’s inhabitants. According to the legend, the devil was so angry about this, that he threw himself into the Serchio river and was never seen again in the area.

28. Taste the famous Brunello Wine in Montalcino

Montalcino is a cute Tuscan city located on a hilltop overlooking the beautiful landscape of Val d’Orcia. After strolling through the old town, I recommend you taste the famous Brunello wine.

You can do this either in one of the many wineries surrounding Montalcino or alternatively in one of several wine shops (Enotecas) in town. We stopped by “Wine & Passion – Vino al Vino” in the city center (Via della Libertà 14) and tasted five different wines. The owner was very helpful and explained all about the wine, how it is produced etc.

Brunello wines are special, as they need to age for at least 5 years, before being fully “ready”. They usually contain 100% Sangiovese grapes. The taste differs according to the minerals in the soil – which is different on each side of Montalcino!

29. Visit beautiful Pienza in Orcia Valley

Pienza is located right between Montepulciano & Montalcino and is situated in the beautiful Orcia valley. Pienza is famous for being considered the birthplace of “Renaissance urbanism”.

In 1405, Aeneas Silvius Piccolomini (there he is again!) was born here and later became Pope Pius II. As the Pope, he rebuilt his entire birth village as the “ideal Renaissance town”, applying early principles of urban planning which later spread to other European centers. The entire town was declared a UNESCO World Heritage site in 1996.

Take a walk through the narrow streets, soak in the vibe and if you are keen on some culture and history, make sure to check out the Palazzo Piccolomini. After walking around town, make sure you take a moment to enjoy the view into the beautiful countryside. This can be done with a good drink or Aperitivo at Idyllium (Via Gozzante 67).

30. Go on an olive oil tasting

One thing not to be missed while on a trip through Tuscany is an olive oil tasting. Olive oil has a rich tradition in the Tuscan kitchen and the region boasts some of the best olive oils in Italy. Many agricultural and family-run vineyards will also produce olive oil, but you will also find some mills specialized on this “liquid gold”.

Some good spots to go on an olive oil tasting are in with Pruneti in San Polo in Chianti, at Pornanino in Radda in Chianti, or Dievole in Gaiole in Chianti.

31. Off the beaten path: Visit ancient Santa Fiora one of the “Borghi più belli d’Italia” in the Monte Amiata region

Monte Amiata is one of the tallest peaks in southern Tuscany and Val d’Orcia area. Especially in Autumn (September & October), this area has its own magic: it is the season of festivities and there are many Chestnut & Mushroom festivals happening in the area, with handmade artifacts, home-cooked specialties, and a lively vibe with many local markets taking place throughout the region.

Mentioned for the first time in 890 A.D., Santa Fiora is a small, cute medieval town located in the more southern Val d’Orcia. Stroll through the Medieval streets and make sure to check out “La Peschiera” in the lower town part.

La Peschiera is a large square filled with crystal-clear water, a reservoir originally created for breeding trout in Medieval times. Towards the middle of the 15th century, it became more of a garden with a beautiful adjoining park, containing pines, silver firms, cypresses, magnolias, etc. and making it a beautiful oasis on a hot day.

32. Stroll through the small streets of Montepulciano and browse through its Art Galleries

Montepulciano was one of our favorite towns while in Tuscany. Situated on a hilltop, it has a beautiful layout, glorious Palazzos, and many spots where you can stop by and admire the beautiful surrounding landscapes.

Moreover, Montepulciano has a vibrant and charming art scene. While strolling through the streets you will stumble upon various small art galleries and art shops. Stop by, browse through and maybe you will find a gem to take back home.

Also, if you are a wine-lover like me, try Montepulciano’s own wine “Vino Nobile”. It tastes best with some delicious food – try Porta di Bacco (Via di Gracciano nel Corso 94/96).

33. Admire the picture-perfect landscape of Val d’Orcia

While there are many things to do in Tuscany, one of the best is to just enjoy and soak in the landscapes. Val d’Orcia is one of the most beautiful and characteristic landscapes in Italy, so just enjoying nature in all its beauty is something not to be missed among all the sights and things to do.

So take a picnic, a blanket, stop somewhere along the road, find a nice spot in nature and just take some time to enjoy and take in the surroundings. A good spot for this is Cappella di Vitaleta (see above).

34. Enjoy as many sunsets as you possibly can

Sunsets in Tuscany are just beautiful. The various colors of the sky and the sun slowly setting over the hills or the rooftops of medieval towns is a beautiful spectacle. So make sure you enjoy these moments consciously and sit somewhere with a view, a few snacks, and a bottle of wine, and just relax and enjoy the moment.

35. Slow down and enjoy the Dolce Vita

Rich and tasteful wine, delicious food, and a slower pace of life: that is partly what makes up the magic of Tuscany. So make sure you take your time to just discover, get lost in the streets, and don’t overcrowd your itinerary. While it is tempting to see as much as possible while you are there, don’t forget to enjoy your trip and slow down to really savor every moment.

And while there are many things to do in Tuscany, I can promise you that you will be back someday, so you can see everything you missed the second time ;-).

So enjoy the moments that you have, treat yourself, and enjoy “Dolce Vita”!

Have you been to Tuscany and have any more recommendations on things that must go on everybody’s itinerary?

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