Tucked between Tuscany and Le Marche, Umbria often slips quietly under the radar – and that’s precisely part of its charm. Here, time moves at its own pace amidst countless medieval villages that crown its hilltops.
Many of these pretty small towns are UNESCO world heritage sites, steeped in centuries of history. They offer an authentic experience, far from the crowds and polished tourist trails. From Todi’s honey-hued piazzas to Assisi's sacred sites, every town in Umbria is unique in its own way.
Chances are you only have limited time in Italy. So, where to begin? We have created a guide to the most beautiful small towns across the region, each with their own charm, history and character. If you are staying in one of our luxury villas in Umbria, these lesser-known spots offer the perfect day out.
Todi
Surrounded by blooming sunflower fields and olive groves, Todi is at the centre of Italy’s lushly green and rugged heart. This charming hilltop town feels delightfully removed from the usual tourist trail, with tumbling streets and tiny alleys frozen in time from the Middle Ages.
Offering fine views from high on its hill above the River Tiber, it comes as no surprise that this small hilltop town was once voted one of Italy’s most liveable cities. After all, it’s home to Umbria’s prettiest square, Piazza del Popolo, the perfect spot to pause and linger with a cappuccino or aperitivo.
We have a select portfolio of villa rental near Todi, so you can slow down, unwind and adjust to Umbria’s laid-back pace.
How to get there:
Getting to Todi takes around 40 minutes by car from Perugia or 2 hours from Rome, making it an easy day trip or weekend escape.
Three essential stops?
Piazza del Popolo, Umbria’s prettiest square; a climb up the bell tower for panoramic views of the Umbrian countryside; and a leisurely stroll around the Tempio di Santa Maria della Consolazione. Read our travel guide to Todi for more local tips.
Montone
Though small in size, Montone is rich in history and charm, offering an authentic experience far from the tourist crowds. Lean into its fascinating history with a walking tour of its palaces and preserved churches.
The main square is framed by authentic trattorias and secret gardens, with towering plants that provide shade in the summer. Enjoy an alfresco lunch to the sound of chirping birds and the fragrant scent of rosemary and wisteria.
How to get there:
Montone is just a 25-minute drive from Perugia San Francesco d’Assisi Airport and about two hours from Rome, making it an easy stop on an Umbrian road trip.
Three essential stops?
L’Antica Osteria for delicious local food and wine; a prestigious film festival in July; and the local Abbey turned museum chapel, which has rare biblical iconography from the late 1400s.
Orvieto
The Umbrian town of Orvieto is one of the most ancient in Italy. Roughly a 90-minute drive from Rome, this tight-packed city is raised high above the Tiber Valley on a dramatic volcanic rock plateau.
A ride on the funicular brings you to the top, where you’ll find the magnificent Orvieto Cathedral and a maze of medieval streets. Underground, a subterranean network of mysterious tunnels and passages reveals the town’s ancient history.
Meeting the locals is a highlight of visiting Orvieto, thanks to its friendly and welcoming community. The wine and olive oil are just as exceptional, with exclusive guided tours available. Slow things down at a family-run trattoria to try local olive oils, salume and black truffles. Coro on Via Duomo is so good it deserves a Michelin-star.
How to get there:
The best way to get to Orvieto is via Rome or Perugia. You can also take the train from Rome or Florence, which drops you just below the town. From there, a funicular whisks you up to the historic centre. For the ultimate freedom, rent a car or speak to our award-winning concierge, who can arrange private transfers to and from your private villa.
Three essential stops?
The Duomo, a masterpiece of Italian Gothic architecture; a wander through the centro storico; dine at Trattoria del Conte, just outside town, for an authentic Umbrian meal.
Spello
This charming Italian village is a must-visit on any Umbrian itinerary. Ringed by ancient Roman walls, its centro storico (historic centre) still preserves remnants of both Roman and medieval architecture. Indeed, the town’s long and layered history can be found just about everywhere – in its cobbled lanes, Gothic churches and flower-filled alleys.
Mostly, though, the real charm of Spello lies in its relaxed rhythm. Amble its cobblestone streets, pause in quiet piazzas and stumble upon family-run trattorias, where meals are made from home-grown produce.
How to get there:
Spello is about a 30-minute drive from Perugia San Francesco d’Assisi Airport and roughly 90 minutes from Rome.
For a seamless journey, speak with our award-winning concierge to arrange a private transfer or car rental, so you can explore the town and surrounding countryside at your own pace.
Three essential stops?
Highlights of Spello include Piazza della Repubblica, the town’s lively heart perfect for coffee or people-watching; Santa Maria Maggiore Church, renowned for Pinturicchio’s Renaissance frescoes; and the majestic Porta Venere with its ancient Augustan walls.
Gubbio
Once a powerful medieval comune, Gubbio has been beautifully preserved, with houses of rosy-pink stone. This remote medieval town feels frozen in time, where narrow streets, ancient palaces and tranquil piazzas transport visitors back through centuries of Umbrian history.
There’s plenty to do in the surrounding countryside to warrant a villa stay. Parco del Monte Cucco offers endless hiking and mountain biking trails. Our local concierge can help you plan the best routes to suit your pace and preferences. Read our guide to Umbria’s national parks for more inspiration.
How to get there:
Gubbio is just over two hours from Rome by train, with connections via Foligno or Perugia, or roughly two and a half hours by car.
Three essentials?
Make the Piazza Grande your first stop, a 3-sided square with views across terracotta rooftops. Then wander to the vast Palazzo dei Consoli which houses the town’s museum and picture gallery. Pause for a picnic atop the Monte Ingino.
Read our travel guide to Gubbio for more highlights.
Montefalco
Situated in the central west of Umbria, Montefalco is locally known as the ‘balcony of Umbria’ for its front-row views of the countryside. Five grand entrance gates set the tone, each leading to Piazza del Commune, the central piazza.
The town is synonymous with Sagrantino grapes, a bold and celebrated red, native to the region. Vineyards surround Montefalco, and many are open for tastings and tours. Equally, you can indulge in a private, sommelier-led tasting from the comfort of your villa near Montefalco.
How to get there:
Montelfalco is a 30-minute drive from Perugia San Francesco d’Assisi Airport and roughly 90 minutes from Rome.
Three essential stops?
Must-sees in Montefalco include Piazza del Comune, the San Francesco Museum and the surrounding vineyards and enotecas for Sagrantino tastings.
Assisi
As the third most visited pilgrimage site in Italy, Assisi is an irresistible destination for history buffs and anyone on a spiritual path. In fact, millions come as an act of faith to visit superbly preserved churches covered in exquisite frescoes.
Religion and history aside, this charming hilltop town enchants visitors with its narrow cobblestone streets and bustling piazzas. Getting lost and stumbling upon a hidden, rosy stone trattoria on a quiet backstreet is all part of the Assisi experience.
Staying in one of our private villas near Assisi gives you the chance to slow down and enjoy the calm of the evenings and early mornings.
How to get there:
By car, Assisi is about two hours north of Rome.
Three essential stops?
Don’t miss the Basilica of San Francesco for its iconic frescoes by Giotto, and a slow stroll along Via San Francesco’s steep alleyways to the Piazza del Comune.
Bevagna
The true joy of Bevagna is adapting to its relaxed rhythm. Home to two of Umbria’s finest Romanesque churches, this pretty small town in Italy’s rugged green heart sits on the western edge of Foligno.
Ringed by ancient medieval stone walls, its charming historic centre, Piazza Silvestri, is exceptionally well preserved, offering a glimpse of Umbrian life as it would have been centuries ago. Save for a 19th-century church fountain, nearly every aspect is entirely medieval.
Step back in time with a look inside the churches of San Silvestro and San Michele. Visitors can find a host of Roman ruins, including a mosaic floor in an ancient public bath, dating back to the 2nd century AD.
How to get there:
Fly to Rome or Perugia for easy access to Bevagna. From Rome, it’s a scenic two-hour drive through rolling Umbrian countryside, while Perugia’s airport is just 30 minutes away.
Three essential stops:
Start with a waltz around Bevagna’s backstreets to the medieval Piazza Silvestri, followed by a visit to the Museo di Bevagna, which showcases the town’s history in a three-part exhibition space. Stop for lunch at La Bottega di Assù if you’re on the way to Gubbio from Rome.
Plan your perfect Umbrian getaway
Italy’s green heart has its fair share of pretty towns and villages. Deciding where to go all comes down to preference. Whether you’re after traditional cuisine, pretty medieval streets or a spiritual awakening, there’s plenty to choose from.
Allow our Villa Specialists to curate your perfect village hopping adventure, offering exclusive access to the finest villas in Umbria. All of our handpicked villas in Umbria come with a dedicated Concierge team included, fully versed in the best local experiences in Todi, Spello, Assisi and beyond.