Visiting Umbria on the way from Rome to Florence


We love Umbria, and a transfer between Florence and Rome is the perfect opportunity to make a stop in this fantastic region you will be passing right through! We suggest getting off the beaten path in Umbria to discover amazing medieval cities, beautiful vistas and delicious food on your way from Rome to Florence.


The region of Umbria is one of the smallest in Italy, yet it offers so much that you could fill days of your itinerary here. However, if you have just one day to explore on your way transferring between Rome and Florence, here are some ideas to stops in Umbria you will love.

As Umbria lies directly between Rome and Florence, it is an obvious choice when looking for a wonderful transfer day trip when going between Florence and Rome. You can explore the very heart of Umbria by visiting the charming cities such as Todi, Assisi, Perugia, or discovering the Montefalco wine region or sparkling bird-watchers paradise, Trasimeno Lake. You can even sneak in a stop in Tuscany in the town of Cortona, just across the border of Umbria, to see what all the “Under the Tuscan Sun” fuss is about.


Wonderful day transfer itineraries through the heart of Umbria

We will come to collect you and your luggage in Rome at your hotel. Upon leaving Rome, we will drive on highway A1 heading north and, in just about one hour, we will already enter the region of Umbria. In fact, our first stop, Orvieto, is visible from the highway in just over an hour.


Umbria Itinerary Number 1 – Orvieto, Wine Tasting and Civita di Bagnoregio

One of the greatest day trips from Rome is the charming hilltop town of Orvieto. If you are continuing on to Siena or Florence, this is the perfect place to stop as it is just one hour outside of Rome, it has incredible architecture, art and historic treasures to visit and great food and wine to enjoy either in the town or at a winery or restaurant in the countryside. The biggest bonus: it’s not far from the eerily beautiful “island” village of Civita di Bagnoreggio. Keep reading to find out about this great itinerary halfway between Florence and Rome.


Orvieto, perched on a hill

After leaving Rome, in just a little over one hour you will already be at your first stop is Orvieto, a stunning city perched on a high, tuff stone hill. It has a massive Gothic cathedral dating back to the 14th century that is worth a visit or at the very least a stop to admire the sparkling golden façade. The underground cave and tunnel system that lies below the town can be visited on an organized tour in English and other languages. The underground area was created by the Etruscans, the region’s first inhabitants, and then further developed over the millennium. There are fascinating artifacts and even an old olive press hidden beneath the city. Let us know so we can book you a spot if this is something you are interested in as the tours fill up fast.


Orvieto wine tasting

If you love crisp, easy drinking white wine, Umbria is a great place for a quick wine tasting. The wine is labeled either “Orvieto” or “Orvieto Classico,” both of which are excellent dry white wines that are usually inexpensive and easy to drink. While the red wine in the region is not as famous as the white, you can still find some great reds to try if that is your preference. If you are a wine lover, let us know ahead of time and we can arrange for you to visit a winery for a tasting.


Civita di Bagnoregio

civita di banoregioNot far from Orvieto, we can take you to spend an hour or two at Civita di Banoregio, a village nicknamed “the city that will disappear,” because of the incredible erosion all around the town. This dramatic erosion has created a stunning badlands landscape that you won’t want to miss. The tiny town has only 11 inhabitants and is connected to the mainland only by a pedestrian bridge. It appears like a small island and is shrouded in silence due to the complete lack of cars.

Umbria Itinerary Number 2- Todi, Montefalco Wine Region, Bevagna or Spello

If you would like to go deeper into the green heart of Umbria and visit places that aren’t on the main tourist itineraries or if you really love fine red wine, then the charming village of Todi, the Montefalco red wine region and then a stop in either Bevagna or Spello is the perfect itinerary for you. Be sure to order a truffle dish at lunch, it’s one of the regional specialties!



A little over an hour outside of Rome you will get off the main A1 highway heading towards Montefalco and skirt beautiful, artificial Lake Corbara supplied by the Tiber River waters, the same river that runs all the way down to Rome. Along this route, it is possible to have a nice stop in Todi, a medieval hilltop city that is rich in beautiful artistic and architectural sites. For example, the city is completely surrounded by ancient walls. The best way to visit this town is to be dropped off in the main carpark outside the city walls and use the inclined lift (called a funicular) to comfortably ride to the top of the hill and reach the main part of the town. You can walk to the main square in the city center and see the Palazzo del Capitano and the main Cathedral. If you are in the town at lunchtime, we can make you a reservation at the authentic trattoria, Pane and Vino (Bread and Wine), serving delicious local dishes and wine (of course!) just a few steps from the upper lift station.


Montefalco Wine Region

You can taste the best Umbrian wine when driving further into the heart of the region to Montefalco. You will see the endless rows of vines and olive trees as you exit the highway and drive along the country roads through this agricultural paradise.

The amazing red wine from the region is Sagrantino di Montefalco. It is made from the grape variety Sangiovese, the same grape variety used to make two of Italy’s most famous wines: Chianti and Brunello di Montalcino. Montefalco is a small walled city, which looks almost exactly the same as it did during the Middle Ages. Be sure to take a quick spin through the remarkable St. Francis Museum located on one side of the main square.

If tasting some awesome wine is your top priority, as soon as you are within the city walls, you can select one of the many indoor or outdoor wine bars or shops that offer various types of wine tasting opportunities, with or without food.

If instead you are looking for a more complete wine experience then let us know ahead of time and we will arrange for a full winery tour and wine tasting at a local winery in the area. Sagrantino di Montefalco wine is not yet as famous as Chianti or Brunello di Montalcino, however we promise that it will not disappoint.

In the Umbrian countryside, besides the incredible wine, you will also find delicious high-quality extra virgin olive oil. Be sure to let us know if you would also like to visit an olive oil producer or mill and we can arrange to take you to a winery that also produces its own extra virgin olive oil or a separate stop.

Leaving Montefalco, the next stop during your visit to this wonderful region could either Bevagna or Spello or Assisi. Keep reading to decide which one is for you.



Bevagna has a place on the “most beautiful villages in Italy” register. This small city lies at the bottom of the valley but its medieval walls, which are built on the primitive Roman ones and are well preserved, extend for more than one mile. The best way to visit Bevagna is to be dropped off just outside the ancient gates to explore the old city during a relaxing stroll. Once you step inside, the main sites are primarily located in the Piazza Filippo Silvestri. You can admire the San Silvestro, San Domenico, and San Francesco churches. The church of San Domenico dates back to the 13th century and is known for its Giotto frescoes. Moreover, this Umbrian gem is filled with excellent restaurants where you can taste the genuine local cuisine and enjoy the down-to-earth nature of the local residents.



spelloJust a few minutes away from Bevagna is the small medieval city of Spello. The town sits on side of a hill, therefore, be prepared for a bit of uphill climbing. You will be dropped off at the bottom by the Roman gate, Porta Consolare, which was built in 1st century BC, and after just a few hundred meters, you’ll reach the 12th century church, Santa Maria Maggiore, where you can admire the famous Baglioni Chapel. This church houses the frescoes of Pinturicchio, known to be his best work, as well as his portrait. It is also worth visiting a Roman house under the local city hall building that dates back to 1st century AD and was discovered in 1885.

If we have some time after leaving Spello, we can arrange for a visit to the Spello Frantoio (olive oil mill). If you have the good fortune of visiting during the fall, your visit might coincide with the yearly olives harvest that happens during October and November each year. When the harvest is going on, the oil mill is in full swing pressing olives for extra virgin olive oil, a fascinating process. If you come any other time of year you can see the mill and taste the local olive oil. We are happy to give you our expert tips for either transporting a small quantity of oil home with you (we will tell you how to do it without ruining your clothes! or how to have it shipped home).  The Umbrian olive oil is known for being some of the best quality oil in all of Italy.


Umbria versus Tuscany

The standout features of Umbria are its natural beauty, the agriculture and wine production, and the hilltop medieval towns that are not quite as famous as their Tuscan counterparts, but just as charming. While Umbria cannot compete with Tuscany in terms of advertising campaigns on a global scale, we guarantee that you will love this region of Italy, which is quickly becoming one of Italy’s top tourist destinations.



Umbria Itinerary Number 2 – Assisi and Perugia


If you love connecting to the spirituality of a place or are fascinated by the life and miracles of St. Francis, then this itinerary to the hometown of St. Francis of Assisi, as well as the nearby Perugia is a must! Thousands of pilgrims flock to the area every year to witness the magic and spirituality of the area for themselves and walk in St. Francis’s footsteps. Keep reading to find out more about Assisi and the chocolate-filled town of Perugia you won’t want to miss while transferring from Rome to Florence on your next holiday to Italy.


Assisi and St. Francis

Assisi is famous worldwide because of St. Francis who was born and died there. Although the son of a wealthy merchant, St. Francis became aware of his higher calling and decided to leave behind all his wealth and live in poverty.


Assisi tour and transferDuring this transfer tour from Rome to Florence you can spend the day walking in St. Francis’s footsteps for a fantastic and mystical experience. You can reach Assisi from Rome in about two and a half hours. Our first stop will be a short visit to the Sanctuary of Rivotorto. This is also known as the sacro tugurio or sacred hovel in English. In 1208, this is the place that St. Francis chose, along with his two brothers, to start his practice of reflection and preaching. In 1455, a new Gothic church was built over the original hut to preserve it. Then, in 1854, the Church was rebuilt because of a big earthquake.

As we drive toward the historic city center of Assisi, we will climb the Subasio Hill. Mid-way up the slope you’ll see the vast St. Francis Basilica and its monastery in a dominating position over the valley below. Like most Umbrian towns, Assisi is a medieval city whose origins date to the Ancient Roman age. Once you reach Porta San Pietro (St. Peter’s Gate), we will leave you to either meet a guide (which we are happy to arrange for you ahead of time!) or explore the town on your own.

The main attraction in Assisi is of course the Basilica of St. Francis, which is about 10-minute walk uphill from the main drop off point. The church construction started two years after the death of Francis in 1226. In 1230, his body was reburied underneath the main altar in the lower Church.

The Basilica of St. Francis is built in two sections: the lower and the upper Church. Both hold inestimable treasures due to the numerous frescoes by famous artists such as Cimabue, Simone Martini and Giotto among others. The church also represents one of the most significant Italian Gothic churches, followed by several Franciscan churches spread among Umbria and Tuscany.

Assisi is the city of churches and convents. Because it is impossible to visit all of them in one day, consider choosing which churches interest you most ahead of time, so you can have a plan for seeing the city.


Basilica of Santa Chiara

One place we highly encourage you to visit is the Basilica of Santa Chiara (St. Clare in English). Clare was still a very young girl when she started to follow Francis in his preaching and then she finally joined him on his religious path at the age of 19. She was also considered Francis’s best friend and was so devoted to him that she spent most of her life doing works in his name and adhering to his doctrine. She also started the order of St. Clare, commonly known as the “Poor Clares.” When Francis died, she was by his side at the Porziuncola, another tiny church chosen by the Saint as the place to spend his last days. Unfortunately, Francis died young from an unknown stomach disease.

The Basilica of Santa Chiara is constructed from pink and white local stones. The construction started immediately after her death in 1253 under the direction of the foremost architect of the time, Filippo Campello. In 1260, the Basilica became Clare’s tomb when her body was transferred from the San Giorgio church to a grave under the high altar. The St. Clare’s Crypt was erected to house the Saint’s relics, which are now on display.


Assisi city center

We highly recommend you take some time to visit the main square, Piazza del Comune, originally the forum of Assisi (in Roman times). The city hall palace is next to the Roman temple, Minerva. In the 16th century, the temple was converted into a Catholic church named Santa Maria Sopra Minerva. This lies on the “decumanus,” the name given to streets in the ancient Rome to indicate it was a main street running on an east-west axis.

If you’ still have the time and energy for more churches, we recommend having a peak into either San Damiano or San Ruffino. We also suggest a visit to the Eremo delle Carceri, an isolated hermitage where Francis sometimes lived. It is a very spiritual place that Francis chose to be able to live in isolation and concentrate on prayer and meditation. It is located next to a convent on Subasio Hill about 800 meters above sea level fully immersed in holm oaks woods.


Santa Maria Degli Angeli

On the way out of town, we’ll wind our way down the hill into the valley below where the small town of Santa Maria Degli Angeli is located. This city was built around a prominent church named Santa Maria Degli Angeli, the Basilica of St. Mary of the Angels. This Basilica was commissioned by Pope Pius V and built in the 16th century. It is a very unique place because it was built over the original tiny chapel known as the Porziuncola. Francis loved this small church so much that he chose to die here. Once you step inside, you will notice it has the smaller Porziuncola inside, a very tiny but complete church with its roof and sidewalls.


Miracle Rose Garden of St. Francis

Our final stop will be the famous rose garden that you can visit where one of the miracles of St. Francis occurred. The legend says that St. Francis had a nightmare, a vision of the devil trying to weaken his faith. Francis resisted him and ran to the rose garden to punish himself. He rolled in the rose thorns as punishment for permitting the devil to come into close contact with himself. A miracle happened when instead of getting hurt by the thorns he emerged from the bushes with a celestial white light and no wounds. In fact, to save the body of Francis, the roses had been transformed into thorn-less roses, which still grow in the same garden today.



After leaving Assisi, the next highlight along this itinerary from Rome to Tuscany is undoubtedly the capital city of the region of Umbria, Perugia, about 20 km north of Assisi.

Perugia sits on a hill, at 493 meters above sea level. Although the name Perugia comes from the Roman name for the town, Perusia, it was actually founded much earlier by the Etruscans. It is still possible to see the Etruscan walls and gates that mark the old city edges. This ancient area is still the main center of the city today and is the uppermost part of the city with restricted car access.

The Perugia city center has two main squares. The first square, Piazza IV Novembre, is the seat of the Priori Palace, which dates back to medieval times. It is famous for the Umbrian art collection housed within since the 13th century. The San Lorenzo Cathedral is a Gothic church located in the same square with significant frescoes and paintings dating back to the Renaissance. Moreover, this square has an interesting fountain, Fontana Maggiore, which is decorated with bass reliefs representing zodiac signs and biblical scenes and occupies the middle of the square.

Perugia is also the seat of one of the oldest Italian universities, founded in 1308, as well as another university for foreigners wanting to study in Italy.

The city of Perugia is famous for its chocolate, including the famous chocolate candy invented in the town called Baci Perugina or Kiss of Perugia! If you are a chocolate lover, you might want to consider coming during the yearly festival in October called Eurochocolate. During the festival the entire town becomes a chocolate-lovers dream, with opportunities to buy, taste and enjoy all kinds of chocolate from the town and from around the world, as well as take master classes and enjoy special meals in the city’s restaurants.

From Perugia the drive on to Florence is around two hours where your transfer-tour will come to an end when you take you to your hotel in Florence or Siena for check in. You will not regret taking the opportunity to see a different side of Italy. Our clients always tell us that these transfer days are often their absolute favorite days during their trip to Italy!


Umbrian & Tuscany Itinerary Number 3 – Trasimeno Lake, Cortona and Arezzo

This day trip-transfer tour from Rome to Florence includes a stop at the sparkling shores of Lake Trasimeno and then a visit to the charming Tuscan town of your choice, such as Cortona or Arezzo. After picking you up with your luggage at your hotel in Rome, we will reach Lake Trasimeno from Rome in just over two hours by driving due north on the A1 highway. This is the perfect transfer tour for anyone who loves the water, birdwatching and nature and also wants to visit the city of Cortona from “Under the Tuscan Sun” or Arezzo and the surrounding area.


Trasimeno Lake

Lake Trasimeno is the largest body of water in central Italy, on the border between Umbria and Tuscany. This lake was formed 3 million years ago from a depression created by geologic fractures, and is not technically a lake at all! Historically speaking, Trasimeno Lake was crucial in the Second Punic War. Hannibal, a Carthaginian general and political leader, was leading the Carthage Army with 50,000 soldiers under his command. He crossed the Alps with his soldiers and 37 elephants, marching against the Roman Republic. On June 21, 217 BC, they crushed the Roman Army, killing more than 10,000 soldiers in an ambush near Trasimeno Lake. Incredibly, archeologists even found at ossuary, very close to the present day town of Tuoro, containing thousands of bones belonging to these poor Roman soldiers.

Today, Trasimeno Lake has a vibrant fishing industry. Tourism is also a huge part of the local economy with numerous lakeside resorts, campsites and hotels. The most important towns include San Feliciano, Passignano, Tuoro, and Castiglion del Lago.

The lake even has three islands, Polvese, Maggiore, and Minore, which can be visited using the local ferry service that connects the mainland to the islands daily. Of the three islands, only Maggiore Island is inhabited year-round.



Unless you’ve been living under a rock for the last 20 years, you have certainly heard of the famous book “Under the Tuscan Sun” by Frances Mayes or the film of the same name. It has inspired endless trips to Italy in search of the beauty and magic of Tuscany. The town of Cortona and the famous “Villa Laura” in the surrounding countryside is where the book and movie are set.

Cortona is located on the southern border of Tuscany, a few kilometers from Trasimeno Lake in Umbria. Below the town is the famous Val di Chiana a valley renowned for its agriculture, especially the Chianina cow breed that is used for its meat, specifically the Florentine T-bone steak. The name Chianina comes from the Valdichiana (The valley on the Chiana River) that lies between Trasimeno Lake and the hill where Cortona is located.

Cortona was founded during the age of the Etruscans under the name Curtun. In the 7th  century BC, Cortona joined the Etruscan League, becoming one of the most important towns. The city of Cortona is encircled by three kilometers of Etruscan walls that can still be seen today and it preserves most of its ancient features, including also the city gates.

Slightly outside the city walls there are important Etruscan chamber tombs. The tomb nicknamed “Sodo” is open to visitors. If you are interested in learning more about the Etruscans, consider a visit to the Museo dell’Accademia Etrusca located in Palazzo Casali with exhibits on Etruscans but also on Roman and Egyptian civilizations as well.

As you stroll through the picturesque streets and medieval squares, you will come across stunning palaces such as Palazzo Comunale as well as beautiful churches like the Cathedral of Santa Maria. Be sure not to miss the city’s most important art treasure: two panels by Fra Angelico in the Diocesan MuseumAnnunciation and Madonna and Child with Saints.

After Cortona you can head straight for Florence, or, if time permits, make one last stop to see Arezzo, which is enroute.



Arezzo is one of the 10 Tuscan provinces. Like Cortona, Arezzo was one of the most important cities of the Etruscan League. In fact, its original name was Aritim. Significant remains of that age are still visible in the city, such as part of the walls. Later, Arezzo became a Roman city and during the early Renaissance it was considered the city of the artist Piero Della Francesca. The artist realized some of his best masterpieces, such as the fresco representing Mary Magdalen, exhibited in the Arezzo Cathedral and others in the Basilica of St. Francis. The Basilica of San Domenico is home to a fantastic Cimabue painted cross from the 13th century.

The main square, Piazza Grande, is designed in a sloping red brick and is famous for the Giostra del Saraceno. The “Giostra” is a medieval knights’ game that takes place once each year. Roberto Benigni’s move, “Life is Beautiful” (1997), was filmed in the this square.

On the off chance you still have time during your day tour, or if you want to substitute one of the previous stops, another amazing place to visit is San Sepolcro where you can delve deeper into the work of Piero Della Francesca.

Your day tour with transfer will end when your driver takes you to your hotel in Florence or Siena for check in. Please remember, all these itineraries can also be done in reverse if you are going from Florence or Siena to Rome during your next Italian vacation.

Share on Social!

Some of our tours

Privacy and Cookies Policy - Terms and Conditions - Copyright