Umbria’s 3 Essential Cities

The region of <a href="https://www.butterfield.com/places-to-go/europe/italy/umbria">Umbria</a> in <a href="https://www.butterfield.com/places-to-go/europe/italy">Italy</a> is known as the nation’s “Green Heart,” thanks to its vast expanses of beautiful natural parks and reserves nestled within its borders. But there’s plenty to see and do in Umbria’s cities as well, whether it’s noshing on some famous chocolate or following in the footsteps of St. Francis.Here are our top three cities in Umbria that you definitely should not miss.<h3>Perugia</h3>As the capital city of Umbria, Perugia charms with an ancient city centre dominated by Italy’s largest fortress, the Rocca Paolina. In fact, Perugia’s history can be seen all throughout town, from Etruscan ruins to medieval fountains and art galleries of national importance, but that doesn’t mean it’s a sleepy town.

Perugia is home to a vibrant university community and the Perugina chocolate factory, home of the famous “Baci” bonbons known throughout the world. In fact, Perugia plays host to a Chocolate Festival each October, and the streets of the old city are lined with stalls of chocolatiers selling their wares, one more impressive than the next.Speaking of festivals, Perugia is also home to one of the most important jazz events in the world: the <a href="https://www.umbriajazz.it/en/">Umbria Jazz Festival</a>. Each summer since 1973, the city welcomes jazz legends and royalty to play under the stars. Notable guests have included B. B. King, Prince, Sarah Vaughan, Herbie Hancock, Elton John and Alicia Keys, just to name a few. Whether looking to have a brush with fame, be transported back in time, or simply satisfy a sweet tooth, there is certainly something for everyone in Perugia.<h3>Assisi</h3>Lovers of the outdoors cannot miss the city of Assisi, set against the breathtaking green backdrop of Mount Subasio. Arguably one of the most famous destinations in the region, the city is home to the Basilica of St. Francis — patron saint of animals and ecology. The glistening white complex and UNESCO Heritage Site, comprising church and monastery across two levels, hosts 13thC frescoes by Giotto and Cimabue detailing the life of the saint, and is so expansive that it can be seen stretching across the hilltop city from miles away.

Assisi boasts many other impressive sites, including the ancient Roman amphitheatre, the Temple of Minerva, and the underground Roman forum located beneath the town’s main square. But if you prefer to stretch your legs like&nbsp;San Francesco,&nbsp;take a hike up to the nearby Rocca Maggiore, a 14thC fortress perched high above the city that offers incredible views of the valleys below. Whether visiting as a tourist or a pilgrim, you’ll find a sweet reverence for the town of Assisi.

<h3>Orvieto</h3>Orvieto captivates from the moment your train rolls into the station: the ancient Etruscan town stands dramatically at the top of a sheer cliff, once a volcanic slope in the south of Umbria. Hop into a cable car for a scenic ride up to the city centre while admiring breathtaking views of the surrounding area and getting a glimpse of the ingenious ways in which the town has been built to persevere throughout the centuries.

Orvieto offers everything a quaint Italian town is expected to provide: a stunning Gothic cathedral, quiet cobblestone streets, and perfect&nbsp;trattorias&nbsp;to sample traditional and delectable dishes of the region. However, there is a secret layer of Orvieto that is sure to awaken your inner Indiana Jones. The city’s underground is host to an intricate system of tunnels, caves and grottoes from the Etruscan and Medieval ages. Most notable is St. Patrick’s Well, a masterpiece of Renaissance engineering which affords visitors the opportunity to plunge 53 metres (175 ft) into the heart of the mount along an impressive spiral staircase. Along with a necropolis, ancient Etruscan temple sites and current archaeological excavations, Orvieto is a fascinating double-face of adventure and scenic charm.

Feeling inspired to experience Umbria’s breathtaking cities for yourself? Join our <a href="https://www.butterfield.com/trip/small-group/tuscany-umbria-walking">Tuscany &amp; Umbria small group</a> trip or get in touch with <a href="https://www.butterfield.com/meet-the-designers/courtney-mundy">Courtney Mundy</a> or <a href="https://www.butterfield.com/meet-the-designers/melanie-neu">Melanie Neu</a> to see how they can craft your perfect <a href="https://www.butterfield.com/trip/bespoke/umbria-bespoke">bespoke</a> adventure to Italy's green heart.&nbsp; &nbsp;

Discover Umbria’s three essential cities—Perugia, Assisi, and Orvieto—where medieval architecture, sacred sites, hilltop views, and rich Italian culture define the region’s heart.

Umbria’s 3 Essential Cities | Perugia, Assisi & Orvieto Guide

Cycle hilltowns and truffle forests, walk Assisi and Orvieto on small group or private bespoke trips through Umbria, with agriturismo stays in Italy.

Umbria Bike & Walking Tours | Butterfield & Robinson

Hidden Gem

Exclusive Access

Timeless Charm

Umbria is Italy in soft focus—misty mornings, monk-strolled lanes and vineyards that roll on forever. Wander cobblestone towns where time politely hit pause, sip olive oil like it’s fine wine (trust us), and bed down in castles-turned-hotels. With Reschio’s rustic-luxe magic and a soundtrack of Gregorian chants, Umbria invites you to slow down—and stay awhile.

The ‘Green Heart’ of Italy

Hike Umbria's valleys, explore Orvieto's underground city and join exclusive truffle hunts on a tailor-made itinerary. Italy's green heart, privately guided.

Umbria Private Tours: Orvieto's Underground City & Exclusive Truffle Hunts

B&amp;R’s Women’s Only trips are designed by women, for women to experience new regions, cultures and communities from female perspectives. Venture straight to the heart of Italy through the regions of Tuscany and Umbria, laden with history, cuisine and natural beauty. Wander on foot and by bike through the Tuscan landscape across fields of wheat, rolling emerald hills, stretches of sunflowers and sun-drenched vineyards&nbsp;connecting from one picturesque village to the next. Immerse yourself in your peaceful surroundings with&nbsp;morning yoga and step into our friend Margot’s estate to savour exquisite wines. Cross into Umbria via shady wooded paths and hills blanketed in wildflowers to your hands-on&nbsp;crostata&nbsp;cooking class. Retreat to Reschio, Italy’s finest hotel, and explore its enchanting grounds before dining in the castle. By the end of this journey, you’ll feel a deep connection to this serene and magical corner of Italy.

Local Connections

Luxurious Stays

Active Adventure

Cycle, stretch, sip, repeat—this is Italy at its most rejuvenating, reinvigoratinng and remarkable. Pedal through sunflower fields, wander wildflower trails, and find your flow with morning yoga. Bake crostata in the hills, toast fine wines at Margot’s estate, and retreat to dreamy Reschio, one of Italy's best hotels. It’s a multi-active escape with just the right dose of magic (and vino).

Wander through the idyllic countryside

The itinerary below is a sample and is subject to slight changes in routes, accommodations and activities. Please download the itinerary for your selected departure for precise details.

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Tuscany & Umbria Women's Multi-Active | Butterfield & Robinson

In Tuscany and Umbria, slow down to a gentle pace of life and wander from golden-hued horizons to lush, verdant lands. Your journey begins tracing the hills of Montepulciano and Val d’Orcia, travelling along age-old routes that were carved into the landscape step by step. Pass vines tended by generations of winemakers and travel through Pienza, a picturesque Renaissance town. In Umbria, indulge in local cuisine and crostata made with our friend Agnieska, and spend a day exploring&nbsp;endless olive groves, flowering meadows and forests. At the end of each day, spend time relaxing at your beautiful hotels—from the brand-new Casa Newton to Monastero di Cortona, a converted monastery, and Hotel Castello di Reschio, a thousand-year-old castle.

Great Walks

One-of-a-kind Hotels

Authentic Food

Walk your way through Tuscany and Umbria, where every trail feels like a love letter to slowing down. Trace ancient paths through Montepulciano and Val d’Orcia, bake crostata with our friend Agnieska, and wander olive groves that roll on forever. With castle stays, Renaissance towns, and a thousand golden horizons, this is Italy at its most soul-soothing.

From the Golden Land to the Green Heart 

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Featured stays

Spend 5 nights hiking between Cortona and Umbria's green valleys in a small group. Truffle-hunter trails, hilltop medieval towns and a converted monastery as