Umbria’s Hidden Gems: Assisi & Perugia

Today, we'll visit Perugia split into Upper and Lower towns connected by a series of elevators and escalators. The modern lower city sprawls across the Tiber River valley while its historic core is draped across the ridges of the foothills of the Apennine Mountains. The upper town could be a museum; it's a pristine medieval centre seemingly untouched by modern life. Cobbled alleys undulate and weave passed Gothic palazzi to piazzas framed by solemn churches.

On our guided tour, we'll split into smaller groups to wander along the Corso Pietro Vannucci, the city's main street, a vibrant pedestrian promenade lined with elegant shops, pavement cafés, and historic buildings, including the Palazzo dei Priori, which houses the National Gallery of Umbria. This wide avenue leads to the Piazza IV Novembre – the heart of the city. Here, you'll find the gothic elegance of San Lorenzo cathedral and the intricately carved Maggiore fountain.

From this bustling square, narrow alleyways beg to be explored - with crumbling buildings bathed in warm hues of peach, ochre, russet, and cream, providing plenty of places to people-watch over a local craft beer, a chilled glass of Orvieto Classico or a creamy gelato.

From the Piazza Italia you can take an escalator down to an underground world hidden within the 16th-century Rocca Paolina fortress. This labyrinth of passages and spaces that made up the bastion of the old medieval city. You can also enter the foundations of the fortress through the Porta Marzia gate, one of the stone portals chiselled into the crumbling Etruscan wall that encloses Perugia. Interestingly, this under-city maze is more than just a tourist attraction – you'll see locals hurrying through it to the bus station!

This afternoon will be free for you to explore more of what Perugia has to offer.

After breakfast, we'll head to Assisi, an elegant hill town, a UNESCO World Heritage Site and a site of pilgrimage. While it's actually the birthplace of quite a few saints, it's most famous as the birthplace of Saint Francis of Assisi, Patron Saint of Italy, the environment, animals, and birds. It should be no surprise that the vast Basilica of St Francis complex, including a Franciscan monastery and two churches, dominates the town.

During our tour this morning, our knowledgeable local guide will explain how St. Francis became highly revered in Italy. We will learn about his early life as the spoiled son of a silk merchant, his renunciation of wealth, and the founding of the Franciscan Order of Monks. The basilica and friary complex, built as a shrine to St. Francis in 1228 - just two years after his death - features an austere exterior. However, the interior tells a different story, with both the upper and lower basilicas beautifully adorned with colourful frescoes, including a renowned series attributed to the famous Florentine painter Giotto. In the crypts below rest St Francis and his friend, benefactor and follower, Jacoba of Settesoli.

After our guided tour, we'll have some free time to explore the old-world town centre with its shuttered stone houses, 'hole-in-the-wall' shops and tiny family-run cafes. We highly recommend the silky ‘strangozzi’ pasta with rich, earthy black truffles - it's a must-try! There's also a varied collection of churches and cathedrals, as well as two medieval castles, Rocca Maggiore and Rocca Minore, which jostle for dominance on the skyline.

Travelling to Lake Trasimeno, lovingly called the Sea of Umbria by locals. The lake gives landlocked Umbria a splash of azure amongst the nearby gently sloping green hills covered with olive groves and thick woodlands. From the lakeside town of Passignano, we will take the ferry across the calm waters to Isola Maggiore, the only island on Lake Trasimeno with a permanent, albeit small, population residing in its small fishing village. As we approach, you'll be able to see the 19th-century Guglielmi Castel can nestled in the wooden hillside.

On our voyage back to Casiglione del Lago, you can enjoy the view of the Castello del Leone or ‘fortress of the lion’, before continuing to Cortona with time at leisure to explore. Hidden in the tight muddle of Cortona's terracotta rooftops, is a maze of narrow alleyways and wide piazzas. The spectacular view from the Piazza del Duomo is a must, leading the eye over the city walls and across the Tuscan countryside.

This evening will be a real treat for truffle lovers and non-truffle lovers alike. We'll dine in the heart of Perugia at a family-owned restaurant specialising in the local delicacy prized for its unique and intense aroma. Socialise with your fellow explorers while admiring the passion of the local family whilst sampling a truffle-based menu. For those who are not fond of the taste, the restaurant will gladly provide an alternative.

We'll start with a journey to Spoleto for a guided tour. Nestled in the foothills of the Apennine Mountain range, the view of its medieval arched bridge leading to the impressive Rocca Albornoziana fortress seems straight out of a historical film. The city behind reflects the influences of both Roman and Lombard rule. The ruins of the ancient Roman amphitheatre contrast with the Romanesque cathedral that shines in pale stone on the Piazza del Duomo.

During free time for lunch, you might be tempted by the smell of the slow-roasted porchetta that's stuffed into sandwiches and sold from streetside stalls.

After time at leisure, we leave Spoleto and set out once again into the rich landscape of the Umbrian countryside to visit a leading producer of Sagrantino di Montefalco wine, made from the black sagrantino grapes that are indigenous to the region. To help you decide whether this dark, full-bodied "vino russo" deserves a spot on your wine rack, we will enjoy a tasting of various Sagrantino di Montefalco wines, paired with typical local products such as delicious cheeses and cold cuts.

Between Umbria and Adriatic is the Marche region, our destination today. Here, we'll visit Italy's greatest caverns, Le grotte di Frasassi - or Frasassi Caves. Discovered by local speleologists in 1971, the incredible karst caves can easily trick the eye with their pure-white walls and icicle-like stalactites and stalagmites.

Our tour will take us into the cathedralesque Great Cave of the Wind as we learn more about their formation over a million years ago, it's impossible to remain unmoved by our magical and beautiful surroundings.

After our visit to the Frasassi Caves, we'll drive through the undulating hills and picturesque groves of Italy, traditionally suited to the cultivation of olive trees. We'll stop at a local olive mill in Bevagna to learn more about the production of this centuries-old tradition. While we're here we'll taste some of the oil produced at the mill alongside some delectable, local accompaniments.

Our last day of Etruscan discovery, will take us to the Umbrian town of Orvieto. Sitting on a natural pedestal atop volcanic rock, Orvieto looks almost at one with the red-hued rock. It's unspoilt, undercrowded and home to some of the most beautiful buildings in Italy. Its standout feature is the Gothic cathedral.

Beneath its medieval centre, lies the eerie underground ruins of another of this mysterious Etruscan civilisation's 12 key cities. A glimpse of this sparse subterranean city can be had from the family owned Well of the Cave, a secret passageway leading to nine caves underneath a traditional pottery shop.

After taking a ride up the tree-lined funicular tracks to the old town, we'll admire the intricate façade of a stunning Gothic building adorned with gilded frescoes, which make it look as though it is illuminated from within.

Following our exploration of Orvieto, we'll stop at a rural restaurant, locally known as an agriturismo. This cozy establishment embodies the spirit of the Italian countryside, nestled amidst rolling hills and picturesque vineyards. Here, we’ll savour flavours that reflect the rich agricultural heritage of the area, with a menu featuring traditional dishes made from fresh local ingredients grown in the heart of Italy.