A Three-Day Escape into Italy’s Green Heart: Umbria
Hilltop towns, winding roads, and a taste of the good life - our long weekend exploring the charm and flavours of Umbria.
Umbria has been quietly calling to me ever since I first wandered through its more famous neighbour, Tuscany. I’d heard whispers of its similar rolling hills and hilltop towns-but with fewer tourists and a slower rhythm. That sounded like a dream I wanted to chase.
It didn’t disappoint. In just three days, we slipped into a version of Italy that felt deeply rooted, richly flavoured, and full of quiet surprises. This itinerary begins in Rome and winds through medieval streets, long lunches, and sweeping countryside views—just as the region begins to bloom with the promise of spring. It really was incredible and the break I would recommend any seasoned traveller to factor into their Italy plans!
Day One – Orvieto & Todi
Begin the morning in Orvieto, a town perched high on volcanic rock with a cathedral that will stop you in your tracks.
• Duomo di Orvieto – the detail on the facade is reason enough to visit, but step inside and you’ll find frescoes that feel almost heavenly.
• Torre del Moro – take the lift partway, then climb the final steps for a panoramic view of the Umbrian countryside. The bells chime every half hour—consider yourself warned!
• Orvieto Underground Tour – an intriguing look at the hidden tunnels and ancient structures beneath the city.
Lunch at Trattoria del Moro Aronne – rustic Umbrian fare and local wine in a cosy, no-frills setting. Delicious food and homely service!
Afternoon: Todi
Drive around 40 minutes to Todi and catch the funicular (or shuttle if it’s out of action). This peaceful town feels untouched in the best way—stroll the cobbled streets, visit small galleries, and settle into Bar Pianegiani in the main piazza for coffee and dolci under the afternoon sun.
Bar Pianegiani, Todi
Evening: Check in at Nikki’s Resort near Umbertide
We stayed in a beautifully converted two-storey barn surrounded by hills that seemed to wrap around us. Every inch of this place was designed with care—for comfort, flavour, and heartfelt hospitality.
Day Two – Gubbio, Lake Trasimeno & Wine Tasting Bliss
Tucked away in the northeast corner of Umbria, Gubbio is an underrated gem—charming, quietly historic, and with just the right amount of quirky energy. It’s the kind of town that feels untouched, with its winding stone streets and stories whispered through every archway.
Morning: Gubbio Wanderings
Spend the morning getting lost in Gubbio’s rich past:
• Cathedral of St. Mariano and Giacomo - serene and atmospheric.
• Palazzo Ducale & Palazzo dei Consoli -two historic buildings that frame the heart of the town and give a glimpse into medieval life.
• Ancient Roman Theatre - almost always empty, beautifully preserved, and perfect for a peaceful pause.
• Colle Eletto Cable Car - equal parts scenic ride and adrenaline kick! The views from the top are worth every second of the wild little ride.
Snack like a local: Grab a Crescia, Gubbio’s signature flatbread sandwich. Whether vegetarian or meaty, it’s simple, delicious, and made to be enjoyed in the piazza or on the go.
Early Afternoon: Lake Trasimeno
After Gubbio, wind your way west to Lake Trasimeno for a slow afternoon by the water. Rent bikes and ride along the lake’s edge or simply sit by the shore at Café Sol, spritz in hand, taking in the late afternoon glow. This is Umbrian stillness at its best.
Winery stop with Long Lunch: Chiesa del Carmine
As the sun dips, make your way to Chiesa del Carmine for a guided tasting followed by one of the most memorable meals of your trip. Think duck ravioli in truffle sauce and that unforgettable orange and ginger gelato I’m still dreaming about. This place is the full Umbrian package-wine, views, and hospitality wrapped into one unforgettable experience. Read more here.
Day Three – Spoleto & Montefalco
As we made our way toward Spoleto, we took a small detour to a town where time felt like it had paused. Here, at Serafino’s, we were met with the kind of welcome you don’t forget. Daniele and his team served us what might just be the best porchetta panino in Umbria- crispy, crackling pork tucked into soft local bread, bursting with flavour. Paired with a chilled glass of local Spoleto wine (for just €2!), and all for under €6, it was a true taste of the region’s soul. No frills, just generosity and pure joy. Park up on the grass like the locals do and wander over.
Mid Morning: Spoleto
After your belly is full begin your day at the Rocca Albornoziana, the fortress overlooking the town. Walk the scenic path and take in the rolling hills. Then wander down to the Cattedrale di Santa Maria Assunta, home to the stunning frescoes by Filippo Lippi-one of my favourites in all of Umbria. Stroll around this beautiful town, taking in every charming street. I had the best Pistachio gelato at Pistacchieria Crispini- highly recommend!
Afternoon: Montefalco
From here, wind your way to Montefalco, known as the “balcony of Umbria” for its incredible views. This elegant hilltop town is also home to Sagrantino, a rich red wine unique to the region.
Stroll the charming Piazza del Comune, then head to Antonelli San Marcowinery for a long, leisurely lunch and a tasting flight of their exceptional wines, read more about my trip to the winery here. Everything about this stop—from the setting to the flavours—captures the heart of Umbria.
Optional detour: On your way home, consider a stop in Rasiglia, the enchanting “village of water.” With stone houses and cascading streams running through its tiny laneways, it feels like something out of a storybook.
Umbria may be one of Italy’s quieter regions, but it doesn’t whisper- it sings. Through its towns, its tables, and its landscape, it gently invites you to pause and savour. Our retreats are built around these moments: the long lunches, the hidden towns, the seasonal shifts. If you’re dreaming of your own Italian escape, join our mailing list to be the first to hear when retreat dates are released - we’d love to share this part of Italy with you.