Tuscany Bucket List: 40+ must-visit places in Tuscany, Italy

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Home to wonderful medieval towns, spectacular hills and countless wineries, Tuscany summarizes the essence of Italy. In this Tuscany bucket list, you will find all the best sights this region has to offer.

Don’t worry if you can’t visit them all, most locals have probably not visited many of them either.

Written by @backpackersintheworld in collaboration with @tuscanyworkinghostel and @meandtuscany

Best time to visit Tuscany

Spring and Summer (April to September) is the best time to visit Tuscany, especially if you’re interested in photography. In fact, these are the best months as the hills start getting their picturesque colours and the weather is warm.

Keep in mind that late July and August are high-season, so you may experience higher prices and overcrowding at the most popular sites.

How to get around Tuscany

The best way to get around Tuscany is by car or van. Public transportation is also an option if your main plan is only visiting the major cities. However, we recommend getting your own car to explore all the places of this Tuscany bucket list. Most of them are in the countryside and it’s great to have the freedom to stop anytime you like.

You can rent a car in all Tuscany’s major cities and airports from about $20 USD/day. Expect lower prices for longer periods and vice versa.

🚗 What do I need to rent a car in Tuscany?

  • A credit card is required for the reservation
  • Non-European Union citizens will need an International Driver’s Permit/License along with your driving license to be able to drive in Italy.

Tuscany Bucket List

1) Florence

Florence is known as the cradle of the Renaissance and is one of the world’s most popular cities. Having such an incredible history, Florence is home to countless artistic and architectural masterpieces. It would be impossible to leave it out of any Tuscany bucket list.

We will leave the full guide to Florence for another time as this city deserves its own, detailed blog post, but meanwhile here are some of the best sights in Florence:

  • Ponte Vecchio
  • Florence Cathedral
  • Uffizi Gallery
  • Palazzo Vecchio
  • Basilica of Santa Croce
  • The view from Piazzale Michelangelo
  • Basilica of Santa Maria Novella
  • Piazza del Duomo
  • Giotto’s Bell Tower
  • Medici Chapel
  • Palazzo Pitti
  • Bargello Museum

2) Pisa

As soon as you hear of Pisa you probably think about its leaning tower.

However, Campo dei Miracoli (Miracles Square) itself groups the Tower, the Cathedral, the Baptistery and the Campo Santo (the graveyard), all of which are incredibly beautiful.

More notable sights in the city include the Banks of the Arno – the vibrant streets bordering the river Arno – and Piazza dei Cavalieri (Knights Square), which gets its name from the headquarter of the Order of Knights of St. Stephen (Palace of the Caravan).

Next to it, you can also find the beautiful Palazzo dell’Orologio (Clock Palace).

Photo by: @twosomepioneers

Pisa, the Baptistery, Tuscany Bucket List
San Giovanni Baptistery, Pisa

TO SEE: Migliarino San Rossore Natural Park

Migliarino San Rossore Natural Park
Tuscany Bucket List
Migliarino San Rossore Natural Park

An astonishing natural sight near Pisa is the pine tree tunnel located in Migliarino San Rossore Natural Park.

Located just 6km out of the city centre, this Park can be easily reached by car, bicycle or even by walk.

Get here early in the morning to capture the magical sun rays across the pine trees.

Photo by: @twosomepioneers

3) Chianti Valley

Known worldwide for its wines, the Chianti Valley groups countless places you should visit to fully experience the beauty of Tuscany. Starting from the north, the towns of San Casciano Val di Pesa, Tavernelle Val di Pesa and Barberino Val d’Elsa should probably make it to your list.

In the Southern part of the Chianti Valley, Greve in Chianti, Castellina in Chianti, Radda in Chianti, Gaiole in Chianti e Castelnuovo Berardenga are the towns you don’t want to miss.

Another place of interest in the Chianti Valley is the Chiantigiana road itself, the road that connects the towns of the southern part of the valley. It is known for being one of Italy’s most picturesque roads.

We have created this map to help you better understand this itinerary:

Spend a couple of days surrounded by endless vineyards and medieval castles, in the valley that fully represents Tuscany’s history and traditions. However, you can also explore this area on a day trip if you don’t have much time.

Castellina in Chianti – @insolitus

4) San Gimignano

Tuscany Bucket List, San Gimignano
View of San Gimignano from “Via Cortennano

One of the best examples of medieval architecture in Tuscany.

San Gimignano is known as “The Town of Fine Towers”, and this is due to the fact that the most illustrious local families used to show their prestige and power by building taller and taller towers.

This resulted in the town having 72 towers, 13 of which still remains today. Originally, the main towers used to be 53-meter tall.

To set a limit to this rivalry among different families, the authorities of the time halved the height of the towers.

The remaining 13 towers of San Gimignano are a UNESCO World Heritage Site since 1990.

Undoubtedly, San Gimignano might also have a little tourist-trap feel, with higher prices and crowded streets. However, it is definitely worth a visit on your trip to Tuscany, even for half a day. It is one of those unique places you will hardly forget.

2 Must-Do things in San Gimignano:

  • Climb one of the towers.
    Currently, you can climb 3 towers in San Gimignano: these are “Torre Grossa“, and the “Torri Gemelle” (Twin Towers). The entrance fee to climb Torre Grossa (the main tower of the city) is €7 and it includes the ticket to the Town Hall and the Picture Gallery as well.
  • Explore the countryside.
    The best angle to fully appreciate the skyline of San Gimignano is by one of the hills in front of it.
    Our favourite viewpoints were the ones in Via Cortennano.

5) Certaldo Alto

A place you don’t read often on Tuscany guides, Certaldo Alto is the old town of Certaldo. It is located on top of a hill and you can either reach it by walk or by cablecar from the main town of Certaldo.

Certaldo Alto is very tiny but incredibly charming hamlet. Its main attractions are Palazzo Pretorio and Boccaccio’s House. While there isn’t really much else to see here, walking around the streets of this little gem alone is worth the visit.

6) Volterra

The charming town of Volterra is located about 30km from San Gimignano. A 7km-long wall surrounds the city. This is the 13th-century city walls, a defence system who was built to protect not only the city centre but also the surrounding fountains, cultivated fields and pastures from foreign invasions.

Volterra is well known for its Etruscan origins and for the many remains belonging to this era.
Some of the places you shouldn’t miss while in Volterra include:

Tuscany Bucket List
Volterra – @cristina_gottardi
  • Piazza dei Priori: the heart of this medieval town. This stunning main square includes Palazzo dei Priori (the current City Hall) and Palazzo Pretorio.
  • The Cathedral and the Baptistery of the Cathedral: built in the XII century, this Romanesque building was later modified in the Renaissance style a few centuries later. The Baptistery, an octagonal-base structure, lays in front of it.
  • The Roman Amphitheatre: built in the 1st century BCE, this 2100-year old amphitheatre, alongside the Roman Baths and the Roman Forum were buried during the Middle Ages. Excavations began in 1950 and the Amphitheatre can be visited today.
  • The Etruscan Acropolis
  • The Municipal Art Gallery
  • The Etruscan Museum
  • The Six Gates in the Etruscan Wall

TIP: if you’re planning to spend a couple of days in Volterra and you want to visit all of the places mentioned above, it may be convenient to buy the Volterra Card. It is a 72-hour pass which allows you to visit the Etruscan Museum, the Municipal Art Gallery, the Alabastro Ecomuseum, the Palazzo dei Priori, the Etruscan Acropolis, the Cisterna Romana and the Roman Amphitheatre. The Volterra Card costs €16. Alternatively, you can just pay for single tickets, which usually cost €5 each.

7) Viale dei Cipressi di Bolgheri

Tuscany Bucket List Bolgheri

On the way to the majestic Bolgheri Castle, which dates back to 1200, the “Viale dei Cipressi” is an incredibly picturesque road and a perfect Instagram spot.

This road is perfectly straight and is bordered by 2400 secular cypresses on both sides, for its own length.

Alongside the road, you will find Tenuta San Guido, the vineyard of the most prestigious Super Tuscan wine: Sassicaia.

To put things into perspective, Tenuta San Guido Bolgheri-Sassicaia Sassicaia 2015 was elected Wine Spectator’s Wine of the Year in 2018.

Check out its exact location here.

Photo by: @guess_90

8) Monteriggioni

Time seems to have stopped in Monteriggioni. This walled town between San Gimignano and Siena is unique even among the already rich Tuscany’s medieval “borghi” list.

The town is very small and sits on top of a hill, surrounded by a 570mt long circular wall crowned by several towers.

Spend a couple of hours in Monteriggioni, wandering around its narrow streets of this medieval borgo.

Monteriggioni, Tuscany Bucket List

9) Siena

Very much like Florence, Siena can’t be described in a few sentences and can’t be let out of a good Tuscany bucket list. There are so many things to see in this city and we can’t recommend you enough to visit it.

The Public Palace of Siena – @theblanko

Siena is one of Italy’s most popular cities, famous for its Palio which takes place twice a year on 2 July and 16 August, but also for its cascading narrow lanes and fine central piazza.

As for Florence, here is a brief list of places you should not miss when visiting Siena:

  • Piazza del Campo
  • Torre del Mangia
  • The Cathedral
  • The Baptistery
  • The Complex of Santa Maria della Scala
  • The Civic Museum
  • The Public Palace of Siena
  • The Church of San Domenico

10) Crete Senesi

Immediately to the south of Siena, you will find Asciano and its Crete Senesi. This unique landscape consists of a range of hills, woods and “calanchi” among villages like Asciano, Buonconvento and others.

Crete Senesi means literally the “clays of Siena”. In fact, the distinctive grey colouration of the soil gives the landscape an appearance often described as lunar.

Some places of interest near Asciano are the Monte Oliveto Maggiore Abbey and the Gallico’s Castle. However, most Instagrammers will recognize Crete Senesi for the next point on our Tuscany bucket list: Agriturismo Baccoleno.

Agriturismo Baccoleno

I bet you have seen this spot dozens of times already.

It is the twisting road leading to the Agriturismo Baccoleno, bordered by cypress trees.

This agritourism is located in a surreal landscape, right in the heart of the Crete Senesi.

Consider staying here on your next trip to Tuscany, or make a quick stop-over and get your beautiful sunset photos.

Photo by: @passiontravelers


Chiusure doesn’t often come first when you think of Tuscany, but we wanted to include it in our bucket list.

It is a tiny, charming medieval town in the Crete Senesi, which makes the perfect stopover while driving through these spectacular hills.

Although there aren’t massive landmarks in this hamlet, the narrow streets themselves and the beautiful views are definitely worth seeing.

Come here for a few hours of relaxing far from the most popular and crowded spots.

Photo by: @alanaheke

Chiusure Best Places in Tuscany

11) Montepulciano

Foodies and wine lovers haven, Montepulciano is possibly one of our favourite places on this list. Montepulciano is another hilltop town, surrounded by vineyards and known for its “Nobile di Montepulciano” red wine.

The town:

The town itself is very very beautiful. Walk on its streets for 5 minutes and you’ll fall in love.

The main square (Piazza Grande) is situated at the highest point of the town and it is dominated by the gorgeous Town Hall and its tower (which you can climb).

Next to it, you will find the Cathedral, other impressive buildings and dozens of restaurants and cafes which surprisingly aren’t insanely overpriced.

Slightly outside of the city centre is the Church of the Madonna di San Biagio, an impressive religious building dating back to the 16th century, which you should definitely visit.

Another interesting sight in the centre of Montepulciano is the Torture Museum, a jump back in time into the reality of the Middle Ages.

🍇 Vineyards and Wineries:

Montepulciano also features several underground wine cellars. These cellars are considered by many as an “Underground City“, which you can explore while sipping a glass of Montepulciano’s Nobile red wine.

Leave the town and suddenly you’ll be surrounded by vineyards. A great idea when in this area is to go on a wine tour in one of the wineries. The best ones being Tenuta Valdipiatta, Az.Agricola Poliziano, Avignonesi, Cantina Fattoria della Talosa and Icario Winery. This is the best opportunity to learn more about the fine process that hides behind a bottle of wine.

🥩 Food & Wine Shops

Back in the town of Montepulciano, an incredible food scene awaits you as soon as you feel hungry. Try the traditional Pici Senesi, a type of hand-rolled pasta similar to spaghetti that is typical of Tuscany.

If you eat meat, you must try the typical Fiorentina Steak at Osteria Acquacheta. This traditional restaurant is easily the best eating experience you can have in town, and sometimes you must make a booking a month in advance.

When it comes to wine shops, every one of them offers degustation in their shops. Learn about the different vintages and try as many wines as you want without spending a fortune for all of those fancy bottles, or bring home your favourite ones.

Val d’Orcia

We have finally got to the main highlight of this bucket list, the type of landscape that everyone pictures in their head when thinking of Tuscany. The untouched, wonderful hills that have inspired many painters, poets and writers.

While the entire valley is worth visiting and exploring, these are the places you definitely can’t miss in Val d’Orcia:

12) Monticchiello

A small, ancient village located 9 km from Montepulciano and 10 km from Pienza. You can visit Monticchiello in just a couple of hours, and it’s absolutely worth it.

Here you can visit the theatre (Teatro Povero), the Pieve dei Santi Leonardo e Cristoforo and the City Wall that surround the city. Its narrow streets and the view themselves are also stunning.

Monticchiello is also popular for the twisting road that leads to the town, enriched by many cypress trees.

13) Pienza

The heart of Val d’Orcia. The tiny town of Pienza is a UNESCO World Heritage Site since 1996 and it is considered as the “Ideal City” and the incarnation of a Renaissance utopia. This is due to the way the “palazzi” and the “piazzas” are organized, a perfectly designed urban area according to the era’s ideals of rationality and humanism.

Pienza is a must-visit place in Tuscany and a must on any bucket list!

The town was realized by request of Pope Pius II between 1458 and 1462, comprising the ancient borgo of Corsignano. Pienza’s geometric perspectives and impressive buildings still hold its charm today.
Make sure you visit Pienza’s Duomo, Palazzo Piccolomini, Palazzo Borgia and the Panoramic Walk.

🧀 FOOD: Pienza is also famous for its pecorino cheese, a sheep’s milk cheese which is then cured in many different types of ways and materials. You will find several shops in town who sell this cheese only, and many others along the way.

Pienza, Best places to visit in Tuscany
Pienza, countryside – Credits: @swissvoyagers

14) San Quirico d’Orcia

10km from Pienza you will find San Quirico D’Orcia. This is considered one of the most charming towns of Val d’Orcia. The main highlight here is the Collegiata di San Quirico, an 8th-century rural church with a baptismal font rebuilt in the 12th century.

Other places of interest are the church of Santa Maria Assunta, a beautiful travertine religious building, and the Horti Leonini, an interesting example of geometrical Italian gardens.

Olive oil is a distinctive product of San Quirico d’Orcia. In fact, you can find many oil mills and oil shops across the town.

San Quirico d’Orcia cypress trees

Located on a hill overlooking the southern part of the Via Cassia, two groups of cypress trees make the perfect background for your Instagram photos.

Tap here for the exact location.

Photos by: @swissvoyagers, @guess_90

Vitaleta Chapel

Cappella Madonna di Vitaleta

This beautiful Chapel is located right between Pienza and San Quirico D’Orcia.

Surrounded by picturesque landscapes, the Cappella Madonna di Vitaleta makes the perfect stopover between these two towns.

Tap here for the exact location.

Photo credits: @lorenzowanderlust x @sinkeviciute_s

15) Montalcino

Montalcino is another delightful top-hill town surrounded by incredible vineyards and landscapes.

Its fortress, Rocca di Montalcino, dominates the town and offer astonishing views. It is possible to climb it and walk around its walls. The entrance fee is €4.

🍇 WINE: The town is located in the land of Brunello, one of Tuscany’s most prestigious red wines. This is another town on our Tuscany Bucket List in which a wine tour may seem almost mandatory. Get your wine glass ready!

Abbey of Sant’Antimo

Abbey of Sant’Antimo is a historic Romanesque abbey in a scenic area. It is located in the hills around Montalcino, about 10km from the town. It is absolutely worth visiting this place!

16) Bagno Vignoni

One of those places that don’t even seem real. Bagno Vignoni is a small town built around the so-called “Square of Sources”, a man-made pool filled with thermal water which dates back to the 16th century. Pieces of evidence have been found about these thermal waters being used by Romans way before the 16th century.

Today the Square of Sources is closed to the public, but you can still admire its beauty while drinking a coffee in one of the bars of the main square or while walking around the streets of this charming town.

No Tuscany bucket list would be complete without visiting this gem in Val d’Orcia.

Bagno Vignoni, Tuscany Bucket List
Square of Sources, Bagno Vignoni

A couple of hundred meters from the Square of Sources you can find the so-called “Parco dei Mulini”, an archaeological site which comprehends the rest of the old mills.

Walk a little bit more down the road and you will finally reach the Ancient Roman Baths. Please note that the water goes through a long series of superficial canals before reaching these pools, making the water almost cold.

17) Castiglione d’Orcia

Castiglione d’Orcia is a delightful tiny village 10km south of San Quirico d’Orcia. In its main square, Piazza Vecchietta, it looks like time has stopped hundreds of years ago. A beautiful travertine well from the 16th century sits at the centre of the Piazza.

Another beautiful place to visit here is the Rocca Aldobrandesca, the most important monument of the town. This fortress was owned by the Aldobrandeschi and was once dominating the very important via Francigena.

Rocca d’Orcia

A few hundred meters from Castiglione d’Orcia is Rocca d’Orcia, an even smaller medieval town. Not many foreigners are aware of its existence, but it’s a well-preserved jewel hidden in the hills of Tuscany.

Here you will find another fortress, Rocca di Tintinnano, which pairs with the Rocca Aldobrandesca in Castiglione. Rocca di Tintinnano rises imposingly on a spur of rock and offers a breathtaking panoramic view.

18) Poggio Covili

Located a couple of kilometres away from Bagno Vignoni and Castiglione d’Orcia, Poggio Covili is probably the most iconic and Instagrammable straight-cypress-tree-line of the world! It is a must on every Instagrammers Tuscany Bucket List.

Don’t get stressed if you need to wait your turn to take a picture! Every day people stop here just for that.

THE CYPRESS TREE: The cypress-tree has a prevalent role in Tuscany as a decoration for roads and pathways. However, it is also a spiritual symbol and it is associated with death (with the most natural and positive meaning). In fact, you’ll often see these trees as loyal guardians of the Tuscan’s cemeteries.

19) Bagni San Filippo

Bagni San Filippo is a wonderful hot spring in Tuscany. While the Saturnia Hot Springs became incredibly popular lately, especially thanks to Instagram, Bagni San Filippo still remains a relatively undiscovered gem, in particular among foreign tourists.

This hot spring is located about 18km south from Bagno Vignoni, and it can be easily reached by car or by bus.
Bagni San Filippo features a massive calcareous formation called Balena Bianca, or White Whale, which is the main attraction of this place.

There is no entrance fee to visit these hot springs.

Please Note: it is prohibited to climb the white whale due to the risk of damaging it, even though many people do climb it anyway.

OTHER HOT SPRINGS: Bagni di Petriolo

Bagni di Petriolo is another free and even lesser-known hot spring in Tuscany. It is located on the other side of Mt Amiata from the Bagni di San Filippo.

These hot springs used to be incredibly popular in the region, even more than Saturnia. However, the free pools of Bagni di Petriolo have suffered after most of its original thermal water flow was redirected the new SPA a few meters away.

This resulted in a free hot spring that is much less appealing than it was before, however, the thermal water here is hotter than the one in the other places. Consider visiting the recently-opened SPA if you are around, while the free pools aren’t probably worth the trip.

20) Radicofani

Tuscany Bucket List Radicofani

A few kilometres away from Bagni di San Filippo, the rural yet elegant town of Radicofani dominates the area from the top of a hill.

The fortress – Fortezza di Radicofani – is once again the main highlight of this little town: it used to be one of the most important strongholds in Italy.

Today it is open for guided tours to help visitors learn more about its glorious past.

Other places of interest in Radicofani may include Pieve di San Pietro, Chiesa di Sant’Agata and Bosco Isabella.

21) Abbey of San Galgano

Between Siena and Grosseto lays the Abbey of San Galgano, a roofless Cistercian Monastery dating back to the 13th century. The Abbey is about 50 minutes from Siena and it’s one of the highlights of this Tuscany bucket list.

This is one of the most prestigious examples of Italian Gothic-Cistercian architecture. The abbey of San Galgano was devastated and looted several times until it was finally abandoned in 1474.

You can visit the Abbey daily from 10 am to 7 pm. The entrance ticket costs €4.

The Sword in the Stone:

Located at a walking distance from the Abbey, the Montesiepi Hermitage hosts the Stone in the Sword.
Visit this Hermitage to know more about the sword and its legend.

22) Saturnia Hot Springs

READ ALSO: Full Guide to Saturnia Hot Springs

The thermal baths of Saturnia are made up of numerous springs which cover a wide area ranging from Monte Amiata to the Albenga and Fiora hills, to Roselle and Talamone. 

These waters are rich in mineral deposits, especially sulphurous, the main culprits of that sometimes annoying “egg” smell

The “Cascate del Mulino” are perhaps the most famous hot springs in Tuscany, made up of several natural pools of hot thermal water and relaxing waterfalls. 

They are open to the public and completely free of charge throughout the year. A must on your Tuscany Bucket List,

23) Pitigliano, Sovana and Sorano

PITIGLIANO: Also called with the nickname of Little Jerusalem -due to the fact that from the 16th century it hosted a large Jewish community within its walls – Pitigliano is today one of the most fascinating historic villages in Italy and an unmissable stop during a trip to Tuscany.

Not only is Pitigliano famous because of its monuments and historical buildings, but also for the “ Vie Cave”, ancient Etruscan communication routes. 

Vie Cave of Pitigliano: Hollowed out by hand in the tufaceous rock, the hollow streets reach 20 meters in height.
They were used in Etruscan times as a way of communication, transport and defence in case of attack, as their high walls guaranteed protection.

The hollow streets also served as a link between village and village and also towards the necropolises.

Today the hollow streets are one of the most beautiful testimonies of the Etruscan history of this area, which are still passable, suggestive and unique in their kind.

Tuscany Bucket List Pitigliano
Pitigliano – @double_e

SOVANA and SORANO: Sovana and Sorano are other 2 charming hamlets near Pitigliano. Also built on tufaceous cliffs, they are part of the so-called “Borghi del tufo”, and they are the best place to visit after a dip in the hot springs of Saturnia.

EXTRA: Civita di Bagnoregio

While Civita di Bagnoregio isn’t technically part of Tuscany, we decided to include it anyway in this Tuscany Bucket List as it’s the perfect detour from Pitigliano and the Saturnia Hot Springs.

Today Civita di Bagnoregio is part of the Lazio region, and it is often referred to as “The Dying Town”.

Etruscans originally settled here over 2,500 years ago. However, due to the several earthquakes, landslides and floods that have threatened its survival since the 17th century, it was largely abandoned.

Even though it is not in Tuscany, make sure to include it in your bucket list.

Tuscany Bucket List Civita di Bagnoregio day trip

24) Castiglione della Pescaia

It is a small, lovely village located on the coast in the province of Grosseto.

Fine sand and clear water are waiting for you on the beaches of Castiglione della Pescaia, in the heart of the Tuscan Maremma.

You can enjoy a different beach every day: in addition to the main bay at the bottom of the town, in fact, you can push yourself to discover the coast to find less frequented coves and beaches in Castiglione della Pescaia.

Tuscany Bucket List
Castiglione della Pescaia – @alessandro_frati

25) I Canaloni del Farma

The big drain of Farma river”: the so-called Canaloni del Farma is a series of puddles dug in the rocks where it is possible to splash and recover from the summer heat. 

The first swimming section that you encounter consists of some natural pools dug by the water itself in a very rocky stretch that the Farma has to face


From Siena take the SS73 or the Siena-Grosseto highway until you reach the village of Monticiano, continue towards Torniella, immediately before the bridge over the Farma river there is a dirt road on the left where you can park your car and continue on foot for about 2km.

This road is wide and easy and can also be travelled by car. At the end of it, there is a short path with short ascents and descents that can be covered only on foot in about 20 minutes until reaching the left bank of the river to your destination.

26) Vetta Amiata

The “Amiata mountain edge” is represented by a monumental iron cross, 22 meters high, made by the craftsman Zalaffi from Siena.

It is visible from the surrounding hills and valleys up to the Tyrrhenian Sea, Umbria and the Val di Chiana. 

On the highest hump, a statue of the Madonna of the “scouts” was installed, while not far away is the statue of S. Giovanni Gualberto. The panorama that can be observed from up here is remarkable, especially if the weather is sufficiently clear.

The lakes of Bolsena and Trasimeno are visible such as some islands of the Tuscan archipelago, the plain of Maremma, the Metalliferous and Chianti hills, up to the heights of Umbria, Sabina and, in particularly favourable conditions, also the city of Rome.

27) Monte Labbro

Tuscany Bucket List

The Monte Labbro nature reserve is a protected natural area of ​​Tuscany, located south-west of Mount Amiata, in the municipality of Arcidosso.

This is an area of ​​great landscape, environmental and historical value. Monte Labbro is accessed from the small village of Zancona.

The landscape of the reserve is particularly suggestive, as it contrasts with that of the nearby volcanic cone of Mount Amiata. 

In fact, the top of Mount Labbro, made up of white limestone rocks, fractured and largely bare, is surrounded by a mosaic of pastures, hedges and cultivated fields, where extensive agriculture allows the maintenance of natural characteristics. 

On the top of Mount Labbro, the presence of some buildings of exceptional historical-cultural importance, dating back to the jurisdictional movement of Davide Lazzaretti.


28) The Medieval festival of Roccatederighi

Roccatederighi is a village-castle of about 700 inhabitants.

It is located in Tuscany, in the province of Grosseto, half an hour from the sea.  From its boulders, on clear days, the sea seems to touch it.

At the beginning of August, the history of Roccatederighi, part of the Municipality of Roccastrada (GR), will be staged by anyone in town thanks to the Middle Ages event in the Borgo. 

For three days the charming village will show old crafts and ancient passions of a medieval past still to be discovered!

29) The Carnival of Viareggio

The Carnival of Viareggio is one of the most important and famous carnivals in Italy. It is annually held in the city of Viareggio and in 2020 the festival celebrated its 146 years.

This Carnival of Viareggio is celebrated over a whole month and attracts more than 600.000 visitors each year.

The Carnival is well-known for its giant, allegorical papier-maché floats (moving theatres towering up 70 feet over the crowds) with the biggest ones weighing about forty tons.

It is an event you should never miss if you happen to visit Tuscany in February. The next dates for the carnival are Saturday 30 January, Sunday 7, Thursday 11, Sunday 14, Tuesday 16 and Saturday 20 February 2021.

30) Mercantia – Certaldo’s Festival

Tuscany Bucket List

Mercantia Festival in Certaldo is Italy’s most important street theatre festival.

It takes place annually in July in the town of Certaldo, and it lasts 5 days.

The entrance is free for the lower part of the town while there is a fee to access the higher part of the town (Certaldo Alta).


31) Castle of Sammezzano

Currently closed to the public

This is an impressive castle built in Moresque style located 40km south from Florence, in the town of Reggello.
The Castle of Sammezzano has 365 rooms and it is privately owned. It is currently closed to the public.

It is hard to believe that such an outstanding building can be abandoned for over 30 years due to a quarrel among different owners, researches for new buyers and old debts.

You can contribute to saving this castle by signing a petition on the FAI website.

Tuscany Bucket List Sammezzano

32) La Verna

La Verna Tuscany Bucket List

La Verna is a Franciscan Sanctuary located in the Tuscan Appennines, about 83km east from Florence.

The closest town is Chiusi della Verna, about 4km away.

The sanctuary dates back to the earliest years of the thirteenth century when Saint Francis of Assisi indicated its location on Mount Verna

Here the atmosphere is peaceful and the nature surrounding the sanctuary holds sway.

You can choose to stay in one of the accommodations which you can check on La Verna’s official website.

33) Monastery and Hermitage in Camaldoli

Hermitage in Camaldoli

The Monastery of Camaldoli is located in the heart of the Park of the Foreste Casentinesi.

Monks founded the monastic complex in 1046 when they built a small hospital in this site. 3 km away from the monastery you will find the hermitage.

The Hermitage sits at 1100masl and it is isolated in the middle of the forest.

34) Lucca

Lucca is a very charming and well-preserved medieval town. Located near the popular Pisa and about 80km from the very touristy Florence, Lucca is a quieter town which also serves as a great base for exploring the nearby mountains (Apuan Alps) and seaside.

When in Lucca, there are two sights you absolutely must visit: Piazza Anfiteatro and Lucca’s City Walls.

Piazza Anfiteatro

Welcome to the square that ‘hugs you’! This square is set in the historical city centre of Lucca and it is completely surrounded by a circle of buildings following its round shape (accesses are via 4 gateways).

Its name and shape are due to a roman Anfiteatro (amphitheatre) that still lays under the square! Not everybody knows that nowadays you can see the old white Amphitheater stones walking the circle from the outside.

During the last century Piazza Anfiteatro was the setting of a public market, and today it is one of the most visited sites of the city by the tourists.

The houses around are private residences built using the remaining structures of the Amphitheatre. Keep this visit to enjoy a good meal as you can sit at one of the restaurants in this unique site.

Piazza Anfiteatro, Lucca Tuscany
Piazza Anfiteatro, Lucca – @meandtuscany

Lucca’s City Walls

This is the second-largest example in Europe of preserved and completely intact walls!

You can enjoy their stunning beauty right at your arrival in the city. The historical city centre stays within its ‘protection’. The access to the walls is completely free and nowadays it has become a large city park among the most evocative in Europe.

Growing on the circle of walls are centuries-old trees which, since the beginning, were planted to consolidate the enormous mass of earth.

The walls are maintained with passion by the people of Lucca who also created a foundation in its name. There you’ll see locals every day, especially in the evening time for the daily walk or run. Don’t miss the beauty of the autumn foliage on the walls!

35) Trekking on the Apuan Alps

The best area for mountain-trekking in Tuscany is indeed the Apuan Alps. The mountains belong to the areas of Garfagnana and Lunigiana (under the province of Lucca).

Certainly a place where locals go, especially during the summer days to find fresh air. Up these mountains, there is much fun for everyone, both families or expert hikers.

Apuan Alps Tuscany Bucket List
Apuan Alps – @meandtuscany

The Apuan landscape is breathtaking and also one of the wildest areas of Tuscany. Enjoy the silence, and the view reaching the region’s coast!

I suggest taking at least a whole day to rise up one of the most popular peaks such as Prana, Pania della Croce and Forato. The most famous shelter is Rifugio Rossi on the mountain Pania della Croce.

One thing you might don’t know is that the heart of these mountains is the famous stone: Carrara Marble. In fact, on the sea-coast side of this mountain-chain, you can find the famous mines where Michelangelo went to choose the marble for his masterpiece the “David”.

Read more about the Apuan Alps on our friend’s website: One Day Hike in Alpi Apuane

36) Ponte del Diavolo

Ponte del Diavolo (Devil’s Bridge) is a pedestrian bridge across Serchio river. It dates back to 1100 AD and it was a bridge of vital importance for medieval pilgrims.

This bridge is situated near the town of Lucca and it is also referred to as “Ponte della Maddalena”.

The peculiar structure of this bridge is what makes it special: it features one large arch flanked by three smaller ones.

The bridge itself is very steep and it must have been somewhat revolutionary at the time.

Check the map below for its location:

37) Fortezza delle Verrucole

The Verrucole Castle was founded by the Gherardinghi family between the X and XIII centuries.

It is situated in San Romano, on a hill 600 metres up in the Alps Apuane, above the village of Verrucole.

The castle is formed by two distinctive buildings, the Rocca Quadra (Square Rocca) at the bottom and Rocca Tonda (Round Rocca) at a higher elevation.

After being abandoned for several years, the castle is today opened to the public after six years of careful restoration.

The entrance ticket costs €5. Check the map below for its location:

38) Montecarlo di Toscana

Hidden in the hills of the Lucchesia, the area of Lucca, Montecarlo is a charming town that features many interesting sights.

These include a well-preserved city wall, the Rocca del Cerruglio (the town’s symbol) and several defence towers along the walls.

Like many other towns across Tuscany, Montecarlo’s quaint surroundings are incredibly rich in vineyards and olive trees.

Get lost on some of the trails around the town and experience Tuscany’s authentic vibes.

View this post on Instagram

Prime luci a Montecarlo

A post shared by Massimiliano Lazzi (@maxlazzi) on

39) Anghiari

Anghiari is a small medieval town located on top of a rocky hill near Arezzo.

Despite not being on top of most travellers bucket lists, this charming hamlet is arguably one of the most beautiful towns in Tuscany.

Make sure to visit Campo alla Fiera from which you can admire the view over the Tiber Valley, the Chiesa del Fosso (Church of the Ditch) and Il Campano (The Bell Tower). Il Conventone and Palazzo Pretorio (which became the Town Hall) are also notable sights of the town.

Anghiari Tuscany Bucket List

40) Via Francigena

The via Francigena is an ancient road and pilgrim route running from France to Rome and then to Apulia, where there were the ports of embarkation for the Holy Land. Its starting point is located in Canterbury, England.

Via Francigena Tuscany Bucket List

The segment of the Via Francigena from Canterbury to St. Peter in Rome is 2,083km long and it takes about 4 months.

Tuscany played a major role in the past as over 380km of the Via Francigena pass-through 38 towns in this region.

Today it is possible to retrace this old pilgrim route in all its length or for just a few segments, and Tuscany is the first choice of many.

You can download a detailed map for each segment of the via Francigena in Tuscany at this website: francigenaintoscana.org


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