Umbria in Spring 2027

Final 2 Places Remaining | Limited to 6 Guests
Explore Our Journey

Umbria in Spring 2027

Final 2 Places Remaining | Limited to 6 Guests
Explore Our Journey

Umbria in Spring 2027

Final 2 Places Remaining | Limited to 6 Guests
Explore Our Journey

the umbria I share with you

I invite you to experience a more intimate side of Umbria, Italy, away from the well-travelled paths.

Limited to just six guests, this personally curated small-group journey unfolds through hilltop villages, family-run farms, artisan workshops and local traditions, with time to know the people and places rather than simply pass through them.

Together, we’ll settle into our 17th-century home among the olive groves and experience Umbria at a considered pace, through shared tables, conversations and encounters that reveal a side of Italy often missed by visitors.

Join me in umbria

14 – 21  May, 2027

Final 2 Places Remaining  |  Limited to 6 guest

I would be delighted to answer any questions personally. – Maria Gentile

BEHIND the journey

I am Maria Gentile, Founder & Curator of Italy in My Pocket.

My connection to Italy began with family and heritage, but over the years it has grown through the friendships and relationships I’ve formed with the people who live here.

I personally curate each journey and I’m there with you throughout our week together. Along the way, I’ll introduce you to the artisans, families and locals who have opened their doors to me — and now, to you.

Whether you’re travelling solo, as a couple or with a friend, with only six guests there is time to get to know one another, share a table, laugh, linger and experience this part of Italy in a much more personal way.

in spring, the roads are lined with poppies, artisans open their doors, farmers tend to their crops and medieval villages filled with the murmur of everyday life

Your room in the hills

Each guest enjoys a private double bedroom with en-suite bathroom, within a beautifully restored 17th-century medieval farming hamlet in the Umbrian countryside.

The hamlet still carries the story of its rural past. Its little piazza, former stables, olive mill, granary and old agricultural spaces have been carefully restored, preserving the character and simplicity of centuries of country life.

Rooms are generous, individual in character and filled with natural light, overlooking the gardens or the little central piazza. Stone textures, timber beams, antique furnishings and warm fabrics create a quiet retreat deeply rooted in Umbrian tradition.

You fall asleep beneath timber beams that have watched over centuries of rural life and wake to the soft light of the Umbrian countryside. Mornings begin slowly over a traditional Italian breakfast, before we gather for the day ahead.

And when we return, there are gardens, quiet corners and the swimming pool to enjoy, giving you time and space of your own before we come together again.

Air conditioning, heating and Wi-Fi are included throughout, bringing modern comfort to a place whose history stretches back centuries.

from those who have walked with me

Martin and Nikki
A bucket list trip is the best description. It is a way of experiencing Italy that is unique, and could not be organised in any other way. It is highly personal, great fun, full of adventures and beautifully organised. The experiences make it immersive in Umbrian culture, and is especially enjoyable if you like artisan crafts and history (...)
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Tim and danielle
Maria our host was amazing. Her attention to detail was second to none. Our accommodation in a 13th century hamlet in the countryside was spot on. Every morning we would receive a hand written note ...The activities were individual and bespoke with some to cater just for me. The relationships with locals is heartfelt. Anything was possible. Maria’s infectious laughter and carefree demeanour delighted all. 10/10 ( ... )
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Day 1 - Benvenuti in Umbria

In the early afternoon, my driver and I welcome you to Umbria and accompany you to our private 17th-century property, where there is time to unwind, unpack, and gently settle into the days ahead.

We then begin our first Umbrian experience with a private visit to a family estate home to more than 1,200 olive trees. Here, you’ll be introduced to the art and history of Umbrian olive oil — its cultivation, traditions, and unmistakable character. Gathered around delicate balloon glasses, we swirl, taste, and learn to recognise the nuanced notes of a truly exceptional oil, guided by the producer himself.

Later in the afternoon, the pace softens. You may choose to relax in our lush garden with a spritz in hand, or retreat to your private space to rest and take in the surrounding views, before we come together again in the early evening.

As the sun begins to set, we gather for our first welcome dinner,  an intimate, unhurried occasion to share a beautiful meal, get to know your fellow travellers, and ease gently into the journey ahead.

 

Highlights: Private tour and tastings. Welcome dinner.

Day 2 - Medieval Perugia and the Artisans

Medieval village in Umbria visited during a curated journey

As morning awakens over our home, we set out for a day immersed in the captivating medieval city of Perugia. We step straight into a 13th-century Franciscan monastery, home to a Weaving Workshop Museum where an 18th-century power loom is still in use. As we approach, the rhythmic hum of the looms draws us inside. Following a private guided visit, you’ll take part in a hands-on workshop, creating your own piece under the guidance of the artisan herself.

The next few hours are yours to wander through Perugia’s medieval corridors, drifting between hidden doorways of small artisanal stores and the sparkle of contemporary boutiques with their distinctive Italian flair. Lunch is enjoyed at a much-loved local osteria, where seasonal ingredients are paired with fine Umbrian wine.

Later in the afternoon, we enjoy an unhurried passeggiata through the cobblestone streets as our private local guide brings Perugia to life — sharing stories of conquests, struggles, and triumphs across the centuries, with insight into the city’s history, art, architecture, and culture.

As the day draws to a close, our driver returns us to our 17th-century home. There is time to relax with a glass of wine and admire the sweeping views, before we gather once more for a traditional Umbrian dinner, enjoyed alfresco as the sun sets and the day’s stories linger.

Highlights: Tour with hands-on workshop. Medieval village.  Private local tour guide.

Day 3 - Truffle Hunt and Candle Crafting

Artisan workshop during a small group journey in Umbria

After a refreshing breakfast, my driver and I set out on a scenic drive spiralling high into the Umbrian mountains, passing through small villages nestled into the hills as we make our way upward. At the summit, we arrive in a tiny village owned by the same family since 1486, where we are warmly welcomed by the custodians, our truffle hunter, and his enthusiastic dogs, already alert to the adventure ahead.

We step into the traditional Umbrian world of truffle hunting as our guide and his devoted canine companions lead us through the woodland in search of treasures hidden beneath the soil. With freshly collected truffles in hand, we pause at the family farm near their flock of sheep to rest and sample their pecorino cheese, accompanied by a glass of prosecco. Back at the family home, we are invited to watch fresh pasta being made before our eyes, ribbons of dough stretched and cut with practiced ease — before gathering at the table for a generous truffle pasta lunch, shared alongside stories of centuries lived in this one small village.

Later in the afternoon, we visit the medieval village of Bevagna, where two artisan brothers welcome us into their tiny, cave-like workshop, perfumed with beeswax and softly lit by candles suspended from the ceiling. Here, you’ll create your own wax and wick using the same methods practised in the 13th century.

We return home to rest as you please, perhaps with a book in our garden with views. As evening approaches, we stroll to a nearby family restaurant for an authentic Umbrian feast. As the sun sets, we share stories and reflections on the journey so far.

Highlights: Family farm experience, private cooking. Medieval village. Hands-on workshop.

Day 4 - Nature and a Dark History

Today we encounter a different side of Umbria, moving away from grand medieval structures toward a gentler beauty shaped by nature and carefully nurtured by human hands over centuries.

Driving through the hills, we uncover hidden oases that must be experienced to be believed, striking, luminous turquoise waters created by the interplay of minerals and sunlight, set against the backdrop of a tiny medieval hamlet. From here, we stroll onward to a waterfall engineered by the Romans more than two thousand years ago, where thundering white tiers reveal a remarkable union of natural force and ancient ingenuity, a refreshing pause in the Umbrian summer.

Midday brings a traditional lunch at a cosy local restaurant, cherished by residents and tucked into a village of just 400 inhabitants, bordered by a gently flowing river.

In the afternoon, we are guided underground in one of Umbria’s medieval villages. Only uncovered in 1979, this hidden network of stone corridors and chambers reveals layers of history, from Roman cisterns to medieval chapels adorned with centuries-old frescoes. As we move through this labyrinth, the weight of centuries becomes palpable, offering rare insight into a lesser-known, deeply evocative side of Umbria.

We return to our 17th-century home for a leisurely early evening at rest, before gathering once more for a sumptuous Umbrian dinner in the gardens.

 

Highlights: Less discovered areas of nature. Medieval village. Private local tour guide.

Day 5 - Village of Flowers and Bookbinding

Hands-on cultural experience during an Umbrian journey

Our morning begins early, while the air is still crisp, as we travel to a small hilltop town set on the slopes of Mount Subasio, built from soft pink stone that gives it a warm, welcoming feel. Its narrow streets lead past Roman walls, old churches, and a well-preserved medieval gate. While flowers brighten the town in spring that continue to thrive in summer, it’s the history and the locals who make it truly special. I’ll introduce you to a few friendly faces before you have time at your leisure to wander and discover centuries-old corridors, browse small artisanal stores, or enjoy a relaxing spritz in the piazza, before we gather again for our small group lunch at an authentic Umbrian restaurant.

After lunch, you’ll become a master bookbinder for the afternoon. A local artisan near Spoleto, will welcome you into his warmly lit workshop, the air filled with the scent of leather, paper, and thread. Step by step, he will guide you as you hand-stitch your own notebook, learning techniques passed down through generations. By the end, you will have a one-of-a-kind memento of Umbria, created with your own hands.

In the evening, enjoy time to unwind  in the fresh gardens of our property, perhaps considering what to write in your new handmade notebook, before we come together again for a candlelit dinner.

 

Highlights: Tastings. Medieval village. Hands-on workshop.

Day 6 - Todi and Deruta Workshop

Today we set out for a village perched on a hilltop in central Umbria, celebrated for one of the region’s most beautiful medieval piazzas, perfectly framed by its cathedral and historic civic buildings. Just beyond the centre stands a remarkable Renaissance church, often recognised as an architectural masterpiece. Here, you may choose to linger on the town’s edge balconies, taking in the sweeping views, or lose yourself in the laneways lined with eclectic little stores, before we gather for lunch at a restaurant run by two sisters whose lively personalities are matched only by the dishes they create, using ingredients sourced from the surrounding farms of their tiny village.

In the afternoon, we travel on to Deruta, a town renowned for its ceramics and the art of maiolica since the 13th century. Shelves brimming with colour and intricate design reveal the skill of artisans whose techniques have been passed down through generations. We step into a working ceramic studio, where clay slabs, scattered remnants, and a turning lathe set the scene for your own hands-on experience. Guided by a generational artisan, you’ll shape your own ceramic piece to take home, learning the craft while hearing the stories that have kept it alive for centuries.

Returning home in the early evening, there is time to refresh at your leisure before we come together once more for a sunset dinner at our 17th-century home.

 

Highlights: Medieval village. Hands-on workshop.

Day 7 - Wine Tasting and Cooking Class.

Our final day begins with a fairy-tale visit to a 17th-century villa set among the rolling landscape near Orvieto. We are welcomed onto this generational, family-run estate for a private visit led by the son of the family, descending into the underground cellars to taste a selection of the estate’s finest Umbrian wines.

Following the tasting, we take part in a hands-on cooking class, preparing fresh pasta together before gathering at a long table beneath centuries-old trees in the villa’s garden. Shared laughter, good food, and wine make this a relaxed and memorable lunch,  a celebration of the journey we’ve shared.

In the afternoon, we travel into the heart of Orvieto to admire the magnificent Duomo, its golden façade a striking masterpiece of Gothic architecture. Afterwards, there is time at leisure to wander the narrow streets, browse for artisanal keepsakes, or enjoy a gelato in the shade — unhurried moments to savour the town in your own way.

We return to our 17th-century home for a final dinner together. Over one last meal, we reflect on the experiences shared, the friendships formed, and the moments that have shaped our time in Umbria, before gently bidding farewell to this remarkable region.

 

Highlights: Wine tour and tasting. Cooking class. Medieval village.

Day 8 - Ci Vediamo Presto

Our final morning in Umbria begins with a relaxed breakfast in the peaceful surroundings of our 17th-century home. It’s a quiet moment to reflect on the days shared together, the experiences, conversations, and friendships formed along the way.

After breakfast, we say our goodbyes. My private driver and I will accompany you to the Assisi station, ensuring a smooth and unhurried transition to your onward journey.

While our time together comes to a close, the connections and memories created here linger well beyond Umbria. Until we meet again. Buon viaggio.

— Maria Gentile

journey details

14–21 May 2027 | 8 days 7 nights
Limited to 6 guests

$9,295 per person | Double or twin room
$9,895 | Private room

A 30% deposit secures your place.

 

What's included

Exclusions

Travelling with family or friends?

For groups of four or more, you may also like to explore a privately curated journey through Umbria, with dates chosen to suit you.

Let's Begin the Conversation

If this journey through Umbria speaks to you, I’d love to hear from you. Whether you’re travelling solo, as a couple, with friends, or considering a private journey for your own group, leave a few details below and I’ll personally be in touch to answer your questions and help you explore what may suit you best.

— Maria Gentile