Step into a world where medieval hill towns meet Renaissance brilliance and the rhythms of rural life flow into the serenity of the sea. From Orvieto’s golden frescoes and Montefalco’s bold wines to Urbino’s palaces and Senigallia’s Michelin-starred shores, this exclusive itinerary reveals Italy at its most authentic and refined.
With private chauffeurs, expert local guides, and insider access, you’ll uncover treasures known only to those who take the slower, more graceful road. Every day invites you to taste, to linger, and to truly live la dolce vita between the green heart of Umbria and the gentle tides of Le Marche.
A selection of high-touch inclusions, designed to elevate every moment.
Step into Assisi’s Basilica as morning light dances across Giotto’s frescoes. Later, the aroma of black truffles fills a rustic Norcia kitchen as you taste the earth’s essence on handmade pasta. In Urbino, Raphael’s youthful genius surrounds you before the road unfolds to the Conero cliffs, where a Michelin-starred dinner overlooks the Adriatic.
This journey doesn’t just show you central Italy — it lets you feel its soul. Balanced between sacred history and coastal serenity, each day flows effortlessly between culture and cuisine, offering you the true rhythm of Italian life.
Highlights:
Your private driver greets you in Rome, ready to guide you into the soft landscapes of Lazio and Umbria. The day’s first chapter unfolds in Orvieto, a hilltop jewel where the Duomo’s striped façade shimmers in the sun and Giotto’s frescoes guard the chapels within. Descend into the Pozzo di San Patrizio, a spiraling feat of Renaissance engineering, before wandering quiet medieval streets.
Lunch is at Cantina Barberani, where crisp Orvieto Classico wines meet pecorino and local olive oil. The journey continues towards Todi, where Relais Todini awaits — a stone manor wrapped in vineyards. Settle in before a relaxed dinner in the hotel’s dining room, where the flavours of the estate’s own produce shape the menu.
*Relais Todini with Breakfast *Private Transfer *Orvieto tour
The morning begins at an easy pace, strolling through Piazza del Popolo and along Todi’s cobbled lanes. The Duomo steps open onto a panorama of the Tiber Valley — a view unchanged for centuries. Late morning, your driver takes you into the vine-covered hills around Montefalco, known as the “balcony of Umbria.”
At Arnaldo Caprai, you enjoy a private tasting of bold Sagrantino DOCG, paired with aged cheeses and cured meats. A visit to a nearby olive mill reveals the peppery freshness of new-season oil. Dinner is at Osteria La Palomba, a cosy, family-run spot where hand-rolled pasta and truffle dishes take centre stage.
*Relais Todini with Breakfast *Private Transfer *Sagrantino tasting and olive oil tasting
Today’s journey crosses gentle plains towards Assisi, where the pink-hued stone glows in the morning light. Inside the Basilica of St. Francis, Giotto’s frescoes recount the saint’s life in timeless colour. The lanes leading to Santa Chiara are lined with artisan workshops and quiet piazzas.
Lunch is at Enoteca Properzio, an intimate wine bar pairing Assisi DOC wines with salumi, bruschette and Umbrian legumes. The afternoon leaves room for a slow wander through the upper town before dinner at Il Vicoletto, where recipes follow age-old monastic traditions. Return to Todi in the evening, the silhouette of hill towns lit under the stars.
*Relais Todini with Breakfast *Private Transfer *Guided tour of Basilica of St. Francis and Assisi
After checking out from your Todi retreat, your private driver will take you to Perugia, the elegant hilltop capital of Umbria. With your expert guide, stroll through Piazza IV Novembre, admire the intricate carvings of the Fontana Maggiore, and step inside the Palazzo dei Priori to explore the Galleria Nazionale dell’Umbria, home to masterpieces by Perugino and Pinturicchio. Continue along Corso Vannucci, lined with Renaissance façades and lively cafés, before enjoying a refined aperitivo with panoramic views.
In the afternoon, the road leads to Gubbio, a medieval gem where honey-colored stone buildings cling to the slopes of Monte Ingino. Explore the Palazzo dei Consoli and its breathtaking terrace before descending through narrow cobbled lanes filled with artisanal workshops.
As evening falls, arrive in Urbino, the UNESCO-listed Renaissance city of Federico da Montefeltro, and check into your hotel, ready to immerse yourself in its timeless atmosphere.
*Albergo San Domenico with Breakfast *Private Transfer *Tour of Perugia and Gubbio
The morning is devoted to Palazzo Ducale, home to masterpieces by Piero della Francesca and Raphael. After a coffee in Piazza della Repubblica, your driver takes you east into the rolling vineyards of Jesi. At Villa Bucci, the cellars open to reveal their most celebrated Verdicchio dei Castelli di Jesi Riserva, poured alongside seasonal antipasti. Lunch follows at Trattoria La Cantinetta, a rustic spot overlooking the hills.
Returning to Urbino, the evening is yours to wander the softly lit streets before dinner at Il Cortegiano, pairing Marche cheeses with local reds.
*Albergo San Domenico with Breakfast *Private Transfer *Palazzo Ducale tour
An early start leads through winding Apennine passes to Norcia, famed for its truffles, cured meats and lentils. In the heart of town, Bianconi welcomes you with a lunch where black truffle tagliolini and aged pecorino take centre stage. The afternoon includes a visit to an artisanal producer for prosciutto di Norcia IGP and pecorino tastings, followed by time in the wildflower meadows of Castelluccio.
*Albergo San Domenico with Breakfast *Private Transfer *Norcia’s black truffle experience
Check out from Urbino and descend towards the sea. Your first stop is the Conero Riviera, where white cliffs meet turquoise waters near Sirolo. Lunch at Ristorante Trattoria Osteria del Moro offers a menu of freshly caught Adriatic fish and shellfish, paired with Rosso Conero.
By late afternoon, arrive in Senigallia and settle into Hotel Bel Sit, where sea breezes and a private terrace welcome you. Dinner is at Madonnina del Pescatore, a Michelin-starred restaurant celebrating innovative seafood.
*Hotel Bel Sit, Senigallia, with Breakfast *Private Transfer through Conero and Senigallia
This relaxed day begins in Ancona, exploring the Duomo di San Ciriaco, perched high above the port, and strolling the lively harbour. Lunch is a light affair in the old town, leaving room for the evening’s culinary highlight: Uliassi, a three-Michelin-starred restaurant where chef Mauro Uliassi crafts a tasting menu that marries sea and land. Between courses, watch the sun set over the Adriatic from your table.
*Hotel Bel Sit, Senigallia, with Breakfast *Private transfer *Ancona tour
Your final day takes you south to Ascoli Piceno, where Piazza del Popolo is framed by Renaissance palaces and the arcades of Caffè Meletti. Savour authentic olive all’ascolana at Ristorante Migliori, followed by a tasting of Anisetta, the town’s signature liqueur. Spend a final afternoon among elegant streets and hidden cloisters before checking in at Palazzo dei Mercanti.
*Palazzo dei Mercanti, Ascoli Piceno with Breakfast *Private Transfer *Ascolti tour and Olive Ascolana tasting
It’s time to check out of the hotel and begin the journey back to Rome. The return trip takes you through landscapes that now feel like old friends. The rolling hills of the Marche region wave goodbye with their sprawling vineyards, and the Apennine mountains stand on the horizon like a sleeping giant. As the road leads you back to the city, you carry with you the unforgettable taste of an authentic Italy—one that still has the power to surprise and move you.
*Private Transfer
