Casentino, Tuscany to Arezzo – Alternative Tuscany Trail

Casentino and the city of Arezzo are off the beaten track destinations in Tuscany. After spending two months living here, let us guide you through an alternative Tuscany trail.

The Casentino valley is the perfect alternative Tuscany trail. Now, Tuscany is truly as magnificent as all the cypress tree-lined Instagram photos depict. What is largely overlooked is the sheer size of the area it encompasses. It’s big and you could be up in Florence but still be a three-hour drive from the famous Saturnia natural springs!

From coastline towns and fishing villages to vineyards in the countryside, the designated ‘Tuscany trail’ ignores a whole side of the region. However, Casentino and Arezzo down to the border of Umbria – the ‘green heart of Italy’ is an easy distance from Florence.

The birthplace of Renaissance masters Michelangelo and Piero della Francesca can’t be bad footsteps to follow in. From nature reserves to quaint villages and a medieval city let’s delve into what to do and see in Casentino, Tuscany.

Casentino, Tuscany Pin

How To Get To Casentino and Arezzo

The closest airport to this area is Florence Peretola which gives you easy access to trains or buses to Arezzo and the surrounding towns. For example, the town we’ve been house sitting in Rassina.

Getting from Florence Airport to the City Centre

You can get buses and taxis to and from the airport but the most convenient is the new tram that opened in 2019. The T2 runs between Florence airport and the main train station. The transit time is 20 minutes and a ticket costs €1.50 for 90 minutes.

Henry, Florence, Italy

Where is Arezzo in Tuscany?

Arezzo is south of Florence on the way to Umbria and borders the two regions. It’s 76 km from Florence and takes around one hour to drive here from the Tuscan capital.

Trains to Arezzo and Casentino

The train is one line and trains to Arezzo from Florence run regularly at a cost of 8 EUR per person at the time of writing this. A good app to install is Italy Train Timetable. Moreover, it gives you up to date times and prices for the trains.

Getting around the Casentino, Tuscany region

If you have no access to a car or can’t hire a car then buses and trains will be your mode of transport. There is a local bus service in Casentino that will run you between Bibbiena and Poppi. Or buses that run to Castel Focognano and Rassina and even up to Verna. The things on this list are perfectly doable with buses but not reliable. You do have to be savvy with the times of buses, therefore pre-planning is required.

Rassina. Casentino, Tuscany - yellow house

Accommodation and where to stay in Casentino, Tuscany

Depending on the type of trip you are planning you can do accommodation in several ways. For instance, for an adventure holiday, you might want to be up in the hills of the Casentinesi national park. Here you’ll find camping spots in places like Camaldoli. On the other hand, choose Arezzo for a city break with day trip options.

An agriturismo is also a fantastic option to live like a local. Moreover, there are lots of these spread across this part of Tuscany. These are in old towns and villages nestled in the hills of Casentino, Tuscany. Alternatively, bring your camping gear and enjoy the surrounding nature.

When to visit Casentino, Tuscany

Spring to Autumn offers consistent, mild, and hopefully, hot weather. This is perfect for sightseeing and the avoidance of a sudden downpour on a hike. There are festivals to enjoy in the summer and autumn (which we will highlight at the end of the article), but winter brings magical Christmas markets to Arezzo and the surrounding towns.

Casentinesi national park – Casentino, Tuscany

This area of Casentino, Tuscany is an extensive and lush national park. It hosts all kinds of fauna and wildlife such as wild boar, European wild cats, red deer, golden eagles, and the eagle owl all living in an untouched nature reserve.

To best experience, this area heads to the ‘Riserva Naturale Integrale Sasso Fratino’. It lies in the middle of the Casentino Forest, Monte Falterona and Campigna National Park. It’s located on the northern side of the Tuscan-Romagna Apennine and there’s exceptionally good hiking in these hills.

Casentino hills, Tuscany

Walks, hikes and outdoor sports

For keen walkers, there are walking routes through places like the ‘sacred forest’ that is 100km in length. However, it takes around seven days to complete. It takes in stunning walks through the forest and religious sites. You would be following in the footsteps of St Francis who took refuge here. There are seven stages and it takes walkers from ‘Lago di Ponte di Tredozio’ lake to ‘La Verna’ where there’s a striking hilltop monastery (more on that further down).

For sporty types you can mountain bike in the park, jump on an e-bike through the Casentino valley. For families, you will find things like donkey or horse rides. There’s also an abundance of fishing around these parts.

In winter there’s a local ski resort called Campigna, where lovers of downhill skiing will find 2 pistes. This is suitable for all levels. There is a black run for the risk-takers and pros. Or choose to go snowshoeing/cross country skiing. Just don’t forget to grab a hot chocolate afterwards!

Casentino Valley mist, Tuscany

Where to eat and drink in Casentino National Park

You will find lots of lovely flavours in Casentino, Tuscany. When it was still lovely, crisp Autumn weather we went hiking and took picnics which was the perfect day out. One day we found a small shop and bought our favourite Italian lunch, a Porchetta roll. In Camaldoli you’ll find restaurants and bars like the Café del Parco for a cheeky coffee and focaccia.

Castel Focognano – Casentino, Tuscany

The area of Castel Focognano is a municipality of Casentino. The location of our house sit, it covers a range of villages and a splendid garden! This really is non-tourist territory around these parts but it’s worth stopping here for a day trip from Arezzo. It’s also perfect if you’re staying in Casentino, Tuscany.

Giardini Toscani in Casentino, run by Brenda Kennelly is a literal field of dreams. She has dedicated her time to planting thousands of peonies and irises. Her flowers travel all around the world (including royal gardens in Spain). She works from 5 am each morning to cultivate the land and tend to her collection of colourful flowers.

The beginnings of the Arno River which flows through the centre of Florence also flows through here in Castel Focognano. You can take in the river with walks or cycle rides alongside it. Part of the river passes by Rassina, the main town in this municipality. Traditionally it was a market trading town.

Pieve Socana Church, Casentino, Tuscany


In Rassina you’ll find a weekly market on Wednesdays which is best for local and cheap vegetables or fruits. Its main attraction is the Tower of Bellavista. In the past Bellavista was used by feuding lords looking to control this part of the Arno River.

Up in the hills, a lovely walk is up to Poggio Magio – a hilltop crucifix. You see these in many parts of Italy, but it offers beautiful views across the valley. It offers the chance to see wild boar if you’re lucky although best from a distance!

Pieve a Socana

Then finally stop in Pieve a Socana and visit Etruscan ruins. Remaining virtually untouched until they were recently uncovered. The ruins are at the back of the Church of Saint Antonino and the alter of the Etruscan temple is underneath the church. Excavation has only gone so far though.

There is lots of information around the site for visitors and our dogs enjoyed their evening walk around here. During the day you’ll hear the singing of the church bells which is also rather lovely. During the summer they receive busloads of tourists coming to see these small but amazing ruins. That does baffle the locals a bit!

Rassina, Casentino, Tuscany

Where to eat and drink in Castel Focognano

We recommend stopping in the tiny but picturesque Pieve a Socana which you can walk up to from Rassina to visit our favourite bar, Bar La Pieve for a coffee, snacks or a beer. They even stock Guinness and Scottish beers which made us feel at home. Grab a pizza from Asterix Pizzeria next door.

Rassina itself has some bars, restaurants and a supermarket too or Bibbiena is a larger town nearby with cheap supermarket options and more places to eat.

Poppi – Casentino, Tuscany

This is a town worth your time. It holds a più belle d’Italia accolade (beautiful place award) and has an impressive castle to explore!

The modern part of Poppi is at the bottom of the hill while the ancient walled town sits in prime position overlooking the Casentino valley. Stroll the streets and visit local boutiques as you walk through porticos from one end of the village to the other. Bookmarked at each end is the impressive Castello di Poppi and ‘Abbazia di San Fedele’ Cathedral.

Poppi Castle, Casentino, Tuscany

Things to do in Poppi

Poppi has a wonderful castle. Built by two brothers Guido Novello and Simone di Battifolle, they lived in the castle as Counts of Poppi with ‘much ease’. Go inside to see the Rilliana library, which holds 25,000 antique volumes including manuscripts and visit the Guido exhibition.

You may also spot the ghost of his bride Contessa Matelda. Matelda would kill her many lovers inside the castle. Eventually, Matelda faced being locked in the Devil’s Tower which you can see on entry to Poppi.

Inside the 13th century, Abbazia di San Fedele is some impressive artworks and a crypt which is not for the faint-hearted. Then head towards Camaldoli Hermitage, a sanctuary and one of the most important spiritual centres in Tuscany. Stop to look inside the Church of Santi Donato e Ilariano, a baroque church which contains Giorgio Vasari’s earliest works.

Jen and Hen, Poppi Castle, Casentino, Tuscany

Places to eat and drink in Poppi

For a restaurant with a view across the valley head to Charlie’s for a lovely meal or wine and cake. Prefer lunch with a castle view? Next to Castello di Poppi, you’ll find an outdoor restaurant and a beautiful place to grab a beer or vino at Il Pratello. The village also has cute looking traditional restaurants which we didn’t eat in but feel free to explore!

Caprese Michelangelo – Casentino, Tuscany

As you drive down switchback roads you enter a valley lined with chestnut trees and you’ve arrived in the home of Michelangelo Buonarotti, the prolific Renaissance artist. Caprese was renamed by Royal Decree after its most famous resident but is also known as having the best chestnuts in Tuscany.

Henry in Caprese Michaelangelo, Casentino, Tuscany

Things to do in Caprese

Lush forests, rivers, and lakes surround this picturesque village in Casentino, Tuscany. If only we had a drone to show you the full extent of these breath-taking views! As you wander through the village, stop by the Church of St John where Michelangelo was baptised.

His birthplace is now the Casa del Podestà museum with casts and recreations of his sculptures, alongside an exhibition of his contemporaries’ work. It’s not all Michelangelo, close by there are walks in the hills, lakes and beautiful churches and a medieval fortress!

jen, casa del podesta, caprese michaelangelo, casentino, Tuscany

Places to eat and drink in Caprese Michelangelo

For such a small village, Caprese has an exceptional reputation for quality restaurants, even appearing in the Michelin Guide! Their chestnuts are renowned across Italy as being the sweetest and tastiest. Each year they hold a chestnut festival which you can find details for further down!

La Verna Monastery

St Francis is a big deal in Italy and to those who practice Catholicism around the world. La Verna in Casentino, Tuscany is somewhere the famous preacher was venerated. The monastery is still active today and perches quite delicately on the edge of a hill with a sheer drop below.

The Franciscan Sanctuary welcomes modern-day pilgrims and visitors. It offers a place to stay for the weary. Walk around the grounds and find beautiful churches and a series of frescoes that detail the life of St Francis. Those who live and work here also make herbal products ranging from ointments, lotions, soaps, medicines, and liqueurs.

The forests that surround La Verna offer stunning scenery and walking routes. This is also something you can do after or before a visit to Caprese Michelangelo which is in a nearby valley.

Casentino walking trail, Tuscany

Arezzo – The Medieval City

Smaller cities always manage to retain a charm that often evades bigger cities. Arezzo is certainly one of the most underrated cities in Italy. It sits on the edge of Tuscany as it crosses over into Umbria, the aforementioned ‘green heart of Italy’. It is only accessible by train, bus, or car as it has no airport.

Arezzo city centre, Tuscany

The city divides into the Medieval centre and the new town. It has all the shops and amenities a European city is accustomed to. You can easily spend hours wandering its quaint passageways and marvelling buildings from bygone eras. Whole streets owned by various powerful families over time have their own distinct style. There’s an emphasis on always looking up as you take in the splendour of Arezzo.

Where to park in Arezzo

We’re including this as we find every time we drive here we use the car park at the train station. This costs money to do and walking up a big ol’ hill. The best car park is the one directly behind Prato Park – Parking Pietri. It’s also next to a handy escalator up to the historic centre. Some parts you have to pay for and some are free, so check which part you’re in.

Prato Park, Arezzo, Tuscany

Things to do in Arezzo

There’s plenty to explore from ancient fortresses, museums, grand piazzas, and beautiful churches. All of this without the crowds normally found in other parts of the region giving visitors a more local feel.

Walking Tour

We found a company offering walking tours called Across Tuscany, unfortunately, they couldn’t accommodate us on their tour the dates we visited. We thought their weekly tour on Friday afternoons for €20 per person seemed like a reasonable deal though. They are also currently running Christmas walking tours! Another option is to look up Air BnB experiences for local tours and even winery tours or cookery classes.

Piazza Grande

The main square of the city is Piazza Grande with its lively atmosphere of cafés, trattorias and gorgeous tower homes including the impressive Astronomical Clock. Dine or walk through the picturesque porticoes of Palazzo delle Logge Vasariane and visit the Chiesa di Santa maria della Pieve and the Grand Art Gallery. It might be best known from the film “Life is Beautiful” by Roberto Benigni. Find monthly antique fairs and annual Christmas markets here. Also the bi-annual Giostra del Saracino (joust). More details below…

Art Museums

Arezzo is a city brimming with connections to art history and antiques. However, one museum not to miss is the National Museum of Medieval and Modern Art inside the Palazzo Bruni Ciocchi. Inside find the 13th-century masterpieces of Margarito, frescoes by Spinello Aretino and a huge Renaissance section. Another option is Giorgio Vasari home-museum. The famous Italian writer and painter lived here and personally, restored the frescoes found in the rooms here.

Arezzo, Cafe, Tuscany


Medici Fortress

This is the place to go for unbeatable city views! Built by the Medici family who you might know from Florence as an all-powerful family with serious money and influence. The Medici Fortress has a pentagonal shape and high bastions that offer a 360-degree view of the city next to Park Prato.

Passeggio del Prato

Next to the Fortress is this beautiful park which is a delight to walk through and there are amazing free views of the city and countryside to enjoy from here. In the summer sit with an Aperitivo in the café or in the winter come here for Christmas markets. All year round this is a magnificent place to have a mellow stroll and enjoy a little bit of nature away from the city centre and check out the Monumento a Francesco Petrarca.

Palazzo Pretorio Library

A library is often not the most obvious tourist attraction, but this is one of the most magnificent buildings in the city. The façade is adorned with coats of arms of the governors and captains that held the town since 1434. Across the street are beautiful sculptures which are equally as impressive.


Arezzo Cathedral (San Donato) is a gorgeous sandstone church next to Prato park designed by Dante Viviani. The Basilica of San Francesco is one of the oldest churches in Arezzo and inside are beautiful displays of religious art and Renaissance frescoes.

Alternative museums

The most exciting museum is the Archaeological Museum with its bronze age weapons. It also holds human remains from the 6th century and has a fantastic history of Arezzo and the surrounding area. Next to the museum is a Roman amphitheatre which is also not something to miss. The Museum of Media and Communications is also another interesting alternative museum for those who love technology.

Arezzo main piazza, Tuscany

Places to eat and drink in Arezzo

Navigating the best places to eat or grab a drink in Arezzo is quite an adventure. Walk along sidestreets and stumble upon places like Liquid Bar for an Aperitivo. Or try Hoppy Lab Arezzo for an Italian craft beer fix. La Clandestina is the perfect combination of cocktail bar and swanky eatery with seasonal produce and twists on classics.

Salt is another great find in the city centre because it’s a swanky bar, café, local designer wear shop and theatre. A great cup of coffee and cake can be found at Eda’s Bakery, a cute little place on Via Garibaldi. A favourite with locals!

Sansepolcro and Anghiari – Extra Daytrips

Two easy day trips from Arezzo are Sansepolcro and Anghiari. Two beautiful, historic towns on the edge of Umbria.


For a dramatic backdrop, Anghiari is a medieval town built on the edge of a hill with an encompassing fortress. Stop here to visit the Borghetto, the oldest medieval settlement. Surrounded by majestic sixteenth-century walls, the Badia castle. Then discover important religious art in Palazzo Taglieschi with its colourful Madonna by Jacopo della Quercia.

Anghiari, Tuscany

Anghiari was also famously the scene of The Battle of Anghiari in 1440 during the wars of Lombardy. Leonardo Da Vinci painted this battle, but it is now referred to as “The Lost Leonardo”. It is believed it is hidden behind a fresco in Salone dei Cinquecento (Hall of the Five Hundred) in the Palazzo Vecchio, Florence.

jen in sansepolcro church


In Sansepolcro there’s an abundance of things to do and see as you walk in the footsteps of it’s most famous son Piero Della Francesca, the Renaissance artist. Firstly, is Museo Civica, a museum with a top-notch collection of art. It includes the Resurrection by Piero della Francesca, Nativity, and a Madonna with the child by Andrea della Robbia. It also has works by Matteo di Giovanni, Raffaellino del Colle and Santi di Tito.

The town’s churches are filled with impressive artworks and frescoes from the Renaissance era. Even if you don’t do churches these are worth stepping into. Don’t miss The Cathedral of Saint John or San Lorenzo for their important artworks.

Other notable churches to visit are the Church of San Francesco (13th century), the Church of San Michele Arcangelo and the Church of Santa Maria delle Grazie and the palatial sixteenth-century Church of the Good Jesus (Buon Gesù).

Gateway in Sansepolcro to the old town, Tuscany

The town of Sansepolcro also has unique museum offerings, such as the Aboca Herbal Medicine Museum in the Palazzo Bourbon del Monte. It has a poison cellar where you can see how deadly ingredients were used to make innovative medicines.

There is a beautiful Stained-Glass Museum. In addition, the Resistance Museum details the rise of fascism and Italy’s involvement in WW2. Nearby is the Riserva Naturale Regionale dell’Alpe Luna forest trails. Finally, on Fridays from March to September, there are weekly flea markets in the town.

Places to eat and drink in Sansepolcro and Anghiari

In the historic town of Anghiari head to the quaint Il Feudo del Vicario, a favourite with locals and visitors for dishes including local pork and wild mushrooms. Osteria Locanda del Viandante is another option with beautiful views over the Tiber valley below.

In Sansepolcro there are many choices for places to eat and drink, we even saw an Irish pub! For those looking for traditional food though there is delicious local food served at Enoteca Guidi We recommend trying a truffle dish from here! Family-run restaurant Ristorante Fiorentino is another great wee place and where you can try Ribollita (bread soup) in cosy surrounds.

Festivals and events in Casentino, Tuscany and Arezzo

Something that this part of Tuscany does well are festivals, medieval fayres, and markets. Let’s look at what to expect on a trip Casentino, Tuscany and Arezzo.

Food and drink festivals

Chestnut Festival in Caprese Michelangelo

The annual chestnut festival is a celebration that takes place during the last two weekends of October. It has market stalls selling local goods and wares, roasted chestnuts, traditional regional food, and entertainment. Most importantly, the picturesque setting is perfect for eating this sweet treat!

Arezzo Street Food Festival

In April every year, Prato Park is home to the city’s Street Food Festival. Food trucks sell all kinds of tasty local specialities like Chianina beef burgers or grilled arrosticini, meat skewers from Abruzzo and artisan desserts and beers. Foodies will be glad to know there are also several food festivals in Arezzo all year round!

Sagra dell’Uva (grape festival) in Subbiano

In September you can enjoy the parades and festivities of this grape festival with bands, folk costumes, and medieval costumes. There are also wagons selling grapes, sweets, chestnuts, wine and vinsanto. Subbiano is a small town and comune in the province of Arezzo and it can be reached by bus from the city.

chestnut caprese, casentino, tuscany

Medieval Fayres

Palio della Balestra in Sansepolcro (second Sunday of September)

This is a crossbow tournament between the men of Gubbio and Sansepolcro. They dress in medieval costumes and use antique weapons to fight it out! Similarly, there are games for everyone to get involved with. There are crafts and finally, of course, it wouldn’t be an Italian festival without food!

Giostra Del Saracino in Arezzo

Officially this starts at the beginning of September. To clarify, this is a highly anticipated event with a weeklong calendar! The Tuscans love to celebrate their past and this is a wonderful homage to Medieval times. It includes a glorious parade of people in historical costumes, drummers, and flag-throwers.

There are special culinary meetups, daily events and it ends with a joust on Sunday. Finally, look out for the competition between the 4 quarters of the city to win the Golden Lance!

Arezzo Markets

Mercati Natale (Christmas Markets) in Arezzo

The Christmas market takes places every year from mid-November to December. Firstly, it has a wonderful light show! This alongside the festivities adds to the magical atmosphere. Moreover, if there is one Christmas market that will surprise you it’s this one. Italy isn’t particularly well known for hosting markets.

In Piazza Grande, there are Tyrolese market stalls and chalet-style pubs selling hot wine, local beers, and hot chocolate. Therefore, the stalls have some lovely hand-made wares, winter plants and cosy knitted hats. Most importantly, it’s also another opportunity to try the famous Caprese Michaelangelo chestnuts without going all the way to the village! You will also find market stalls and fairground rides in Prato Park. Finally, find more stalls throughout the city’s side streets.

Fiera Antiquaria (Antiques Market) in Arezzo

This city is also renowned for having a sleuth of antique shops, a weekly antique market, and the oldest and biggest antique fair in Tuscany and perhaps Italy! During Autumn it takes place around the end of August on the last weekend and the start of September. In addition, it takes place in the city’s main square on Piazza Grande and spills out into the city.

Arezzo Christmas Market, Tuscany

Now you are very much in the know of what to expect from Casentino, Tuscany. A breathtakingly beautiful part of Italy. Feel free to look through our guide to the neighbouring Umbria region. If you’re interested in house sitting let us help you get started with the process!

Casentino, Tuscany - Alternative Tuscany Trail Pin

37 thoughts on “Casentino, Tuscany to Arezzo – Alternative Tuscany Trail

  1. Awesome post, so much detail. I have never been anywhere in Italy before. But I think the Tuscany area would be my top location to visit first!

  2. Wow! All of the towns you went to were gorgeous! I am definitely keeping this blog post handy because I’m heading back to Central Italy in the fall of 2020 and want to revisit Tuscany. 🙂

    1. Thank you! It’s a beautiful part of Tuscany and you could even nip over to Umbria if you’re in Arezzo 😍 I lived there for 4 months last year and it’s equally as lovely x

  3. Tuscany is still on my never ending bucket list! Thanks for sharing, pinned it so I can enjoy it later!

  4. I love going off the beaten path, so thanks for sharing some additional options. Arezzo looks like a great place to visit. Also two months in Italy sounds fabulous!

  5. Love that you are choosing all these off the tourist track places in Tuscany. I have a guide on Italy for just this and Poppi happens to be in that guide! I have to get there as it sounds wonderful as do all the destinations you mention.

  6. Italy is my all time favourite country and these less known Tuscan towns are so gorgeous. As always a beautiful and detailed post.

  7. What a great post as Tuscany is such a gorgeous area of Italy! The last time I visited was probably 15 years ago and I don’t think I went to Arezzo. Now I’m motivated to go back for another visit! 😁

  8. I’ve always wanted to visit Tuscany because of some parts of my family heritage, but now I’ve got another reason to go: the Christmas and antique markets!

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