12 Charming Assisi Streets with Best Views & Medieval Vibes

Planning a trip to Assisi? Check out these most photogenic Assisi streets with superb views of the medieval architecture and lush green Umbrian countryside

Assisi is a magically atmospheric Italian town that transports you right to the Middle Ages. Having been continuously inhabited for the past 3,000 years, it has been shaped and reshaped by successive generations building on top of the structures left by their predecessors – everyone wanted to live within the protective confines of the city walls.

The medieval streets of Assisi gradually spread over Roman roads, their course altered in the intervening centuries as more buildings were constructed in every inch of available space. The resulting maze of streets and back alleys is wonderfully irregular, with unexpected twists and turns running up and down the slope of Mount Subasio, often opening up to fantastic views of the valley of Tescio below.

Assisi charming medieval streets

I spent 3 days exploring the town and one of my favourite things to do in Assisi was finding these gorgeous back alleys with particularly picturesque architecture and superb views. Here are some of my favourite Assisi streets.

Assisi Streets with the Best Medieval Architecture

There are adorable back alleys hidden all over Assisi, but the two best areas are around St Francis Basilica and San Rufino Cathedral, at the opposite ends of town.

The streets and alleys near St Francis Basilica tend to have fantastic views, so I will describe them in the next section. Here I will concentrate on San Rufino Cathedral area.

Side Alleys off St Maria delle Rose Street – Via S.Maria delle Rose

Sunset in Assisi
Sunset in Assisi

With your back to San Rufino Cathedral, you are looking down via S. Maria delle Rose. This street leads to some of the most adorably irregular alleyways in all of Assisi. Plan to spend at least half an hour here.

Walk along the street for a few meters until you reach Quo Vadis – an incredibly charming B&B with views over medieval rooftops from its rooms. This is where I stayed in Assisi, and you can read my review of Quo Vadis, if you are looking for a gorgeous place to stay in town.

Just past Quo Vadis, there is a little lane – Vicolo della Forteza ducking downhill on your right. Follow this lane, then walk down vicolo S. Agata until you come to the meeting point of three different alleyways with a house standing at the convergence of these alleys, some of which run uphill and others downhill from this point. It’s the most tangled-up arrangement of streets in town.

Things to do in Assisi -get lost in the maze of medieval streets
Maze of irregular medieval streets

Next, walk through the arch onto vicolo del Cipresso. Here a very hardy cypress tree is growing among the walls and pavement of the street. It is amazing that the tree is able to survive and flourish, by the looks of it, in such a uniformly paved environment. Its roots must run very deep.

Now make your way back up to via S.Maria delle Rose and explore the back alleys running up the hill. You’ll find that Vicolo della Forteza re-emerges on your left heading uphill. There are more converging laneways uphill, and if you haven’t been to Rocca Maggiore yet, you can follow these laneways up the hill all the way to the fortress.

It’s about a 10-15-minute waddle to the base of the fortress and you get lovely views of San Rufino and Santa Chiara basilica through the cypress trees that line the hill.

Perlici Street – Via Perlici

Starting from Porta Perlici or the Perlici Gate, via Perlici runs downhill through a particularly atmospheric part of town. If you were to purposefully walk down the street, it will bring you to San Rufino Cathedral in about 5 minutes. But you would miss out on seeing some very photogenic back alleys.

Assisi street

As you head down the street, you’ll notice on your right a brass tap and a small basin built into the wall. This is part of an ancient aqueduct that still brings water to the town from the mountain springs.

Next, you’ll see various vicolos branching off the street. Follow a few of them, they are quite short. Don’t worry about getting lost, as long as you walk downhill, you’ll end up on Piazza San Rufino. Plus, there is plenty of signage around.

The twisting alleys around via Perlici hide some adorable porches lined with potted plants and decorative tiles, houses built at the convergence of two lanes, and Hobbit-sized arches leading down more alleys.

Via Dono Doni

Assisi Streets at night - Via Dono Doni

Back at Piazza San Rufino, there is another adorable street that takes you to Assisi of the early 13th century. This short steep street has been frozen in time, like most of Assisi. The doorways are set into medieval arches, houses are built over the narrow alleyway linking the neighbouring houses and creating a vaulted tunnel below.

Even the pavement here is from the times of booming trade in Assisi – it’s laid out from the famous pink limestone from the quarries on Mount Subasio.

Assisi Streets - Vicolo delle Scalette

I particularly liked this street in the evening when the darkness hid any traces of modern times, leaving the street illuminated by a few wrought iron-clad medieval street lights. It always made me feel like I was a character in a medieval film or book. The realism is a little spooky but very atmospheric.

Assisi Streets with Superb Views

Spilling down the side of a mountain, many Assisi streets have breathtaking views of the medieval rooftops, the city wall, and the green expanse of the Valley of Tescio. Often these views are framed by centuries-old buildings and medieval gates, just like they were during the Middle Ages.

St Margherita Church – Chiesa Santa Margherita

San Francis basilica in Assisi

My favourite viewpoint in Assisi is the town’s most picturesque hidden gem. Looking for a nice vantage point to photograph St Francis basilica I was wondering along the twisting medieval alleys or vicolos that branch off from Via San Francesco.

Meandering without any particular purpose I followed a very picturesque Vicolo San Nicholas and came to a tiny square with magnificent views of the basilica and Umbrian countryside.

View from church of Santa Margherita in Assisi
View from church of Santa Margherita

The square is so small, it’s not marked on Google Maps. It lies at the front of an unassuming 13th-century church – Chiesa Santa Margherita. And because it’s well concealed among the maze of back alleys, hardly anyone comes here.

The easiest way to reach the square is via Vicolo Santa Margherita, just around the corner from Porta San Giacomo (San Giacomo Gate) – the one with the olive tree growing on top. Or follow Vicolo San Nicholas up the hill from via San Francesco. It’s only a short stroll through some of the best medieval architecture in town.

It is a serene little spot. There are two wooden benches at the square facing the panoramic view over the stone wall. If you come here for sunset, you’ll likely have the view and the square all to yourself.

Fontebella Street – Via Fontebella

Things to do in Asissi - rooftops of Abbey of St Peter
Rooftops of Abbey of St Peter

Starting at the Basilica of San Francis, Via Fontebella has some of the best views in town. About halfway along the street, there is a gorgeous viewpoint over the rooftops and the green countryside below. The best view is from the metal terrace next to Hotel Giotto. While this is not the viewpoint marked on Google Maps, it is the most panoramic view on Fontebella Street – almost 180 degrees.

The view takes in the ornate rooftops of Chiesa di San Pietro (St Peter’s church) and the surrounding buildings and opens up to the brilliantly green fields of the valley below.

A few meters up the street, next to Fontebella Palace Hotel, there is another viewpoint – this one is framed by two buildings and a charming wrought iron street light hanging off one of the walls.

Things to do in Assisi - see the view from Fontabella street
View from the official Fontebella viewpoint

Another few meters up the street, there is a third viewpoint, marked as Panoramica on Google maps (Via Fontebella, 15). And if you haven’t had enough of this particular view, walk up Vicolo Degli Esposti, past Bar Sensi and climb up a few stairs to get another view framed by the buildings. Bar Sensi is a lovely small patisserie that sells a wide range of traditional Assisi sweets and is a great spot to enjoy the view with a cup of coffee.

Illuminati Alley – Vicolo Illuminati

View from Fontabella Street in Assisi
View from Fontabella Street

How could you pass an opportunity to go up Illuminati Alley? And the best thing is – there is a stunning view from the stairwell just before this alley climbs up to Via Fontebella.

The view is similar to what you see from Fontebella Street, framed by the rustic walls of two buildings on the sides of this steep narrow alley. Vicolo Illuminati is one of the most picturesque streets in Assisi, so you might like to walk the full length of it, it’s not long. If you’d rather walk downhill, then start on via Fontebella and walk down to Via Monsignor Giuseppe Placido Nicolini.

San Damiano

San Daniano monastery in Assisis

San Damiano was the first monastery of the Order of Saint Clare – the Poor Clares. The theme of holy poverty seemed to reoccur all over medieval Europe, just think of barefoot Carmelites of Avila in Spain. This rustic and charming 12th-century church and monastery is located a 15 min stroll downhill (and a slower waddle uphill on the way back) through tranquil olive groves towards the lush green Umbrian countryside of the valley of Tescio.

This is not a single viewpoint, rather the entire walk is one long view of gorgeous green fields framed by the iconic spire-like cypress trees and distant hills. You can enjoy the views from the little plaza in front of the monastery, or you can walk a little downhill to the little Cantico delle Creature B&B that has unobstructed views of the valley.

The Big Castle – Rocca Maggiore

San Rufino Cathedral viewd from Rocca Maggiore in Assisi
San Rufino Cathedral viewd from Rocca Maggiore

Rocca Maggiore is a fortified castle guarding the citadel of Assisi from the top of the hill, across the valley from another hill, topped by a smaller fortress – Rocca Minore.

Visible from much of the town, Rocca Maggiore appears to be quite a hike away, but in fact, it’s only about a 10-minute steep walk from San Rufino Cathedral. Follow the signposted stairs of Vicolo San Lorenzo and they will take you right to the base of the castle.

Sunset view from Rocca Maggiore in Assisi
Sunset view from Rocca Maggiore

Once on top of the hill, walk to the furthest end of the castle ‘plaza’ for fantastic views over the Basilica of San Francisco. It’s a lovely walk early in the morning or late in the afternoon when the forest on the side of the hill is bathed in warm light, birds are chirping in the trees, and locals walking their dogs dressed in cozy winter doggie coats.

The sunset views of San Rufino Cathedral, Santa Ciara church and San Francis Basilica are particularly striking from Rocca Maggiore.

Don Aldo Brunacci Terrace – Terrazza Don Aldo Brunacci

Secret view in Assisi - Don Aldo Brunacci Terrace

This is another hidden gem that I discovered while looking for the Roman Tunnel. There is a hidden observation deck – Terrazza Don Aldo Brunacci that can be accessed through a car park on Viale Galeazzo Alessi, near San Rufino Cathedral. As you walk into the boring-looking foyer, following the sign to Tunnel Romano, take the elevator to the top or walk up the stairs. You come out at Terrazza Don Aldo Brunacci with beautiful views of the town and Santa Chiara basilica.

If you are interested in checking out the Roman Tunnel, follow the terrace and you’ll soon reach it. This area is filled with Assisi’s Roman heritage (you can find more details in my guide to Roman Assisi). At the end of the tunnel, walk up the steps and you’ll emerge at Plaza Matteotti – Assisi’s main bus station.

St Clare Church – Basilica di Santa Chiara

Assisi view from Basilica di Santa Chiara

Basilica di Santa Chiara, and particularly Via Borgo Aretino that runs between Porta Nuova and the basilica have some unobstructed panoramic views over the Tescio valley framed by the wall and the bell tower of Santa Chiara. There are stone benches that run the entire length of Borgo Aretino Street which make for a perfect spot to enjoy your lunch and the views

Popolo Tower – Piazza del Comune & Torre del Popolo

Best views in Assisi - Popolo tower

Located on Assisi’s main plaza – Piazza del Comune, adjacent to the magnificent colonnade of the former Roman Temple of Minerva, Popolo Tower is the iconic feature of the town. This 47-meter tall tower commands sweeping views over Assisi and the valley below. But… the protective wire mesh at the top makes photography all but impossible. Unless you use your phone camera and position it between the wires.

View from Popolo tower in Assisi

The view is quite good. It sweeps over cloud-shrouded Monte Subasio, the green fields of Tescio Valley stretching out to the horizon and the medieval rooftops of Assisi below.

You can climb the tower on Fridays, Saturdays, and Sundays. And the tickets (5 euros) can be purchased at the Tourist office on Piazza del Comune.

Quo Vadis B&B – Room with a View

View from Quo Vadis b&b in Assisi
View from Quo Vadis

And if you would like a room with a view over medieval rooftops, consider staying at Quo Vadis. It is a gorgeous boutique hotel that does not charge boutique rates. The owners live in the same house upstairs, so you’ll be staying in an authentic Assisi house, a historic palace, in fact.

The hotel part on the ground level is completely separate from the house upstairs, so you’ll have all the privacy of a hotel with the warmth and care of a lived-in house. And waking up to a view like this you completely forget what century you are in. You can read my review of Quo Vadis for more details and photos.

Plus, the hotel is located on Via S.Maria delle Rose, right opposite San Rufino Cathedral and the maze of irregular back alleys behind the hotel is one of the most picturesque medieval areas of town.

How to get to Assisi

Assisi is conveniently connected by train to RomeFlorence, Perugia and other major cities. The journey from Rome takes about 2 hours on a direct train and about 2.5 hours with a change at Foligno. You can check train schedules and buy your tickets online.

The tickets bought online already have a date and time stamp and don’t need to be validated. You don’t even need to print your train tickets. If you download the Omio app, you can simply show your ticket in the app to the conductor.

Things to do in Assisi - walk the medieval streets

Assisi train station is located in the valley, about 5km from the walled town. The taxi costs about 20 euros. There is also a bus (Line C) that will take you to the historic town centre. You can get your bus ticket at the little newsagent store inside the train station.

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