Come and discover an enchanted territory between Marche, Emilia-Romagna and Tuscany
Historically, this territory was disputed between the Malatesta family of Rimini and the Montefeltro family of Urbino, and it was finally annexed by the Dukes of Montefeltro. A long history that can be seen from its many fortresses and castles.
You will admire magnificent mountains, gentle hills, deep gullies and rocky spurs. You will discover how the culinary traditions of the Marches, Tuscany and Romagna blend to produce a unique alchemy of flavors!
PERIOD:
All year round
your souvenir
Beautiful views and wonderful encounters
Duration
5 days and 4 nights
Accommodation facilities
During this journey of discovery through the Montefeltro, you will spend your first two nights in the charming village of Pennabilli, staying in an adorable stone B&B in the heart of the historic centre – the perfect place to immerse yourself from the very beginning in the authentic atmosphere of the Montefeltro.
For the following two nights, you can choose to stay directly in the historic centre of Urbino, allowing you to experience the city at its most peaceful after the day-trippers have left, or opt for a completely different setting: an ancient farmhouse surrounded by greenery near Urbania, with a swimming pool and plenty of space to relax.
travel journal
DAY 1 – ARRIVAL IN PENNABILLI, THE VILLAGE OF THE TWO CASTLES
Arrive in Pennabilli in the afternoon, where a charming stone B&B awaits you in the heart of the historic centre – the perfect place to immediately immerse yourself in the authentic atmosphere of the Montefeltro.
Pennabilli is known as the “village of the two castles”, and its story began with the coming together of two ancient communities: Penna and Billi, once separate settlements marked by rivalries and disputes. In 1350, they decided to unite and sealed their union with a peace agreement, giving rise to the Pennabilli we know today.
But this small village has many other surprising stories to tell. One of the most fascinating is that of Fra Orazio da Pennabilli, a Capuchin missionary who left for Tibet in 1712 and spent much of his life in that distant land, learning its language and culture and creating a remarkable connection between this little village in the Montefeltro and Tibet.
The Dalai Lama visited Pennabilli twice, in 1994 and 2005, leaving numerous reminders of this special encounter throughout the village, from the Dalai Lama’s Mulberry Tree to the Lhasa Bell.
You will find yourself surrounded by a magnificent landscape: Pennabilli sits within a true natural amphitheatre of mountains, with the Monte Carpegna massif on one side and the other peaks of the Montefeltro on the other. A spectacular backdrop that accompanies you throughout your discovery of the village.
And what about dinner? Here, you will be spoilt for choice!
You are in a true crossroads of culinary traditions: Marche, Tuscany and Emilia-Romagna meet in this borderland, creating a wonderful combination of flavours, recipes and traditional local products.
You can simply walk to a Michelin-starred restaurant, or drive just a few minutes to discover the story of one of the most characteristic products of these hills: Formaggio di Fossa, a cheese traditionally matured underground in special pits. You will learn about this ancient production method and the history behind it, before enjoying a dinner centred around the cheese and other local specialities.
Or, if you prefer to experience the village in a simpler and more relaxed way, you can settle into one of the restaurants in the main square and enjoy traditional local cuisine.
Overnight in Pennabilli.
DAY 2 – SAN LEO, MAIOLETTO AND RURAL LIFE IN THE MONTEFELTRO
After breakfast, set off to discover one of the most spectacular places in the Montefeltro: San Leo.
Perched dramatically on a massive rocky outcrop, the village overlooks the Marecchia Valley and preserves one of the area’s most fascinating fortified complexes. Visit the Fortress of San Leo and discover the military architecture and defensive techniques that once made this strategic stronghold virtually impregnable. You will also learn more about one of its most fascinating prisoners, Giuseppe Balsamo, better known as Cagliostro.
For those who would like to add a walk to the day, it is possible to reach Maioletto, where the remains of the ancient fortress stand dramatically on a rocky spur surrounded by the distinctive badlands of the area.
Here, history meets one of the Montefeltro’s most dramatic natural events: on 29 May 1700, a huge landslide, following around forty hours of torrential rain, destroyed the ancient village of Maiolo and led to the settlement being permanently abandoned.
Today, the remains of the Rocca di Maioletto offer spectacular views across the Marecchia Valley, towards San Leo and, further away, San Marino.
In the afternoon, leave the villages and fortresses behind for a while and step into the heart of rural life in the Montefeltro.
Choose between different experiences with people who still live and work these hills today: visit a small Cashmere goat farm, meet the farmers and discover how this precious fibre is produced, or visit a farm where goats graze freely, learn about the work of the farm and finish with a tasting of its products.
An afternoon spent meeting people, animals and real stories, and discovering a side of the region that is rarely encountered along the usual tourist routes.
Return to Pennabilli and overnight.
DAY 3 – URBINO AND URBANIA, BETWEEN THE RENAISSANCE AND TRADITIONAL CRAFTS
After breakfast, it is time to leave Pennabilli and head towards Urbino, the great Renaissance city of the Montefeltro.
The day is dedicated to discovering Urbino, capital of the Duchy of Montefeltro and one of Italy’s finest examples of a Renaissance city, now recognised by UNESCO as a World Heritage Site.
Wander through its streets to reach the magnificent Palazzo Ducale, the heart of the court of Federico da Montefeltro, and lose yourself among the narrow lanes, historic palaces and elegant squares of the old town.
From the Albornoz Fortress, you can admire Urbino from above: a compact city spread across the hills, with the Palazzo Ducale dominating the landscape. A kind of Renaissance capital in miniature, where art, architecture and history come together within a remarkably small space.
If you have chosen to stay in the area around Urbania, you can also devote some time to discovering this charming town, formerly known as Casteldurante, historically linked to the Duchy of Urbino and particularly famous for its long tradition of artistic ceramics.
Urbania is also home to one of the area’s most unusual sights: the Church of the Dead, which houses the so-called Mummy Cemetery, with 18 naturally mummified bodies displayed behind the altar following exhumations carried out in the 19th century. A fascinating story somewhere between curiosity, tradition and mystery.
Overnight.
DAY 4 – ADVENTURE AND THE FLAVOURS OF THE MONTEFELTRO
The fourth day is dedicated to an experience in nature or an encounter with one of the Montefeltro’s most iconic products: truffles.
In autumn, winter and spring, the more adventurous can experience the excitement of rafting on the Burano and Candigliano rivers, tackling rapids and calmer stretches of water as they make their way through one of the most beautiful natural landscapes of the Pesaro hinterland.
For those who would rather follow a more gastronomic path, head towards the Furlo Gorge and Acqualagna, an area renowned for its truffles.
Here, you can join an experienced truffle hunter and his faithful dog on a genuine truffle hunt, learning to read the signs of nature and discovering the secrets behind this precious product.
And naturally, the experience ends with a tasting dedicated to truffles and other local flavours.
Return and overnight at the same accommodation.
DAY 5 – GRADARA OR SAN MARINO AND DEPARTURE
After breakfast and check-out, choose which final experience to enjoy before heading home.
1) GRADARA – HISTORY, LOVE AND THE MIDDLE AGES
Head to Gradara, one of the most fascinating fortified villages in the Marche, and stroll along its medieval streets and ancient walls towards the magnificent Rocca di Gradara.
The fortress dominates the surrounding landscape and is inextricably linked to the story of Paolo and Francesca, the famous couple immortalised by Dante in Canto V of the Inferno. According to tradition, it was within these walls that their tragic love story unfolded.
But Gradara is about much more than Paolo and Francesca. Its strategic position between the Montefeltro and the Adriatic coast made it a coveted stronghold for centuries, contested by the region’s most powerful ruling families, from the Malatesta to the Sforza, and later the Della Rovere.
An encounter between landscape, history and legend that makes Gradara one of the most fascinating stops on the journey. Its connection with the nearby Monte San Bartolo also reveals this area as a meeting point between the Montefeltro hinterland and the Adriatic Sea.
2) SAN MARINO – A REPUBLIC ON MONTE TITANO
Alternatively, head to San Marino, the world’s oldest surviving republic, dramatically perched on Mount Titano.
Explore the historic centre, wandering through its ancient streets, squares and famous towers along the ridge, with spectacular views across Romagna and towards the Adriatic coast.
Free time before bringing the journey to an end.
PRICEStarting from 250€ per person
the fee includes:
• Accommodation for 4 nights – B&B basis (breakfast included)
• Visit to local producers on Day 2
• Guided tour and entrance fees in Gradara or San Marino
the fee does not include:
• Transfers to and from the accommodation
• Meals
• Optional experiences recommended in the programme
• Anything not specifically mentioned under “What’s included”
SUGGESTED MENU FEATURING FOSSA CHEESE
Starters
• Squacquerone cheese flan on Fossa cheese velouté
• Cream of porcini mushrooms and beans on bruschetta
First courses
• Wheat Stringhetti with vegetables, lardo di colonnata and fossa cheese
• Mezzelune with hazelnuts and courgettes
• Potato gnocchi with Fossa cheese sauce and black truffles
Main courses
• Tagliata of Scottona with Cervia salt and rosemary
• Scortichino with balsamic vinegar and fossa cheese
• Fillet medallions with green pepper
Various side dishes, dessert of your choice, water, wine, coffee and digestive.
Do not hesitate to contact us for more information or to customise your trip!
The package is available from 2 participants.
Contact us for any specific need.
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