Country Roads of Tuscany & Central Italy

Choose from a hand-picked selection of Perugian restaurants for a Dine-Around evening. Select the ambience and menu that appeal to you, making dinner a more personal way to experience Umbria’s capital.

Perugia’s dining scene reflects the region’s affection for seasonal produce and distinctive local flavours. This organised choice offers the pleasure of exploring a restaurant that suits your tastes while sharing an intimate culinary experience in the city.

Meet your Travel Director and fellow travellers over dinner at a local restaurant in Rome. Taste Roman specialties in a setting chosen to introduce the flavours of Lazio, rather than simply provide a meal.

Roman cooking draws character from straightforward ingredients and closely held traditions, from fresh pasta to regional cheeses. The shared table offers a welcoming introduction to the city and the people travelling with you.

• 4 Dinner (D)
• 8 Breakfast (B)
• 1 Lunch (L)

• “One thing I really love about showing guests about Italy is how art and beauty can be found around every corner of some of Italy’s cities, which are real open air museums.”
• “One fun fact people don’t usually know before they come to Italy is that the Italian alphabet only has 22 letters.”
• “I really love about showing guests the huge variety that Italy has to offer, from quaint countryside villages to cities full of stupendous art and architecture.”

Insight Vacations

• Business class coach with extended leg room
• Top-rated dining, from farm-to-table to local restaurants
• 4 & 5-star stays

See St Peter’s Square in Vatican City, the monumental public space framed by Bernini’s sweeping colonnades. Take in the obelisk, fountains and grand facade of St Peter’s Basilica from the square.

For centuries, pilgrims have gathered here for papal ceremonies and blessings. Its vast scale and carefully designed approach make this a striking introduction to the Vatican; the experience is a view of the square, not an advertised visit inside the basilica.

Visit Rome’s Colosseum with a Local Expert and examine the immense amphitheatre built for public spectacles in ancient Rome. Look across its tiers and arena while hearing how crowds, performers and gladiators experienced this elaborate setting.

Completed in the first century CE, the Colosseum remains one of the clearest expressions of Roman engineering and imperial ambition. Expert commentary helps bring its surviving stonework into focus as a place of both entertainment and power.

Join Giovanni and his dog Chris for a truffle hunt near the Umbrian village of Baschi. Learn how a trained dog locates these prized fungi and why truffles hold such a special place in the region’s food culture.

Watch Chef Lorenzo demonstrate pasta-making and enjoy lunch accompanied by Orvieto Classico wine. Together, the woodland search and kitchen demonstration connect Umbrian ingredients with the skills used to bring them to the table.

Explore Perugia with a Local Expert, navigating its layered network of streets, alleys and arches. Walk along Corso Vannucci towards the historic centre, where the Palazzo dei Priori and Fontana Maggiore anchor the main square.

Umbria’s hilltop capital preserves centuries of civic life in its pale-stone buildings and underground passages. The guided walk reveals how medieval streets and public spaces fit together in a city shaped by its steep terrain.

Meet Marta and her team of weavers at Perugia’s Laboratorio Giuditta Brozzetti. See how traditional looms are used and learn about the patterns and techniques passed between generations of Umbrian artisans.

This MAKE TRAVEL MATTER® visit highlights a women-owned workshop that provides education and employment opportunities for local women. Hearing directly from its makers gives the textiles a deeper meaning: each piece helps sustain a living craft and its place in Perugia’s cultural heritage.

Explore Assisi with a Local Expert, from its preserved medieval lanes to the 13th-century Basilica of St Francis. Step inside the basilica to learn about its celebrated frescoes and their influence on later Italian art.

In the valley, see the Church of St Mary of the Angels, associated with the final days of St Francis. Assisi’s hillside setting and enduring religious heritage give these landmarks a powerful sense of place beyond their architectural beauty.

Walk Siena’s narrow medieval streets to Piazza del Campo, the city’s distinctive shell-shaped square. See the Town Hall and imagine the square transformed for the Palio, Siena’s fiercely contested horse race.

The Campo has long been the centre of Sienese civic life, its sloping brick surface drawing the eye towards the Palazzo Pubblico. Its unusual shape and living traditions make it more than a picturesque piazza: it remains a gathering place with a strong local identity.

Choose to visit Siena Cathedral with a Local Expert as one of two included Insight Choice experiences. Explore the city’s great medieval church and discover details of the architecture and artistry that express Siena’s historic wealth and ambition.

The cathedral is renowned for its striped marble and richly worked interior. Expert interpretation places its craftsmanship within the rivalry and devotion of medieval Tuscany, offering a closer look at a landmark that shaped Siena’s identity.

Choose to taste panforte in Siena as an alternative included Insight Choice experience. Sample the city’s dense traditional sweet, made with fruits and nuts, and get to know a flavour closely associated with Tuscan celebrations.

Panforte has deep roots in Siena, where recipes balance sweetness with warming spice. This tasting offers a different way to understand the city’s heritage: through a local food tradition that has endured alongside its medieval streets and piazzas.

Explore San Gimignano with your Travel Director, winding through serpentine streets and hidden squares beneath its surviving medieval towers. Their striking skyline has earned the Tuscan town its nickname, the “Medieval Manhattan.”

At Piazza della Cisterna, taste artisan gelato from Sergio Dondoli, a world champion gelato maker known for distinctive flavours. The tasting adds a contemporary craft to a visit defined by stone lanes, historic towers and the atmosphere of a remarkably preserved hill town.

Walk through Florence with a Local Expert to view the marble-clad Cathedral of Santa Maria del Fiore, crowned by Brunelleschi’s dome. See Giotto’s bell tower and the baptistery’s celebrated Gates of Paradise before visiting Piazza della Signoria.

The piazza’s sculptures and civic buildings evoke the artistic and political energy of Renaissance Florence. This guided exploration concentrates on the city’s defining public spaces and their extraordinary concentration of architecture, craftsmanship and history.

Enjoy a farm-to-table dinner in the Tuscan countryside, with dishes prepared from locally grown ingredients. Savour homemade pasta and regional flavours alongside traditional Chianti wine, surrounded by the rural landscape near San Gimignano.

The featured farm, Il Vecchio Maneggio, grows produce among its vineyards, olive groves, saffron crop and orchards. A drink with views across the hills sets the scene for a meal rooted in the land and the people who cultivate it.

Visit Bagno Vignoni, a small Tuscan village celebrated for its mineral-rich thermal waters. Take in the historic spa-town setting and the great water-filled basin that gives its central square an appearance unlike other Italian piazzas.

Travellers have sought out the village’s warm springs for centuries. Its compact stone buildings and unusual centre reveal how bathing culture shaped this settlement in the Val d’Orcia, making it a distinctive stop in the Tuscan countryside.

Visit Pienza, the Tuscan hill town reshaped in the 15th century as an ideal Renaissance town. Discover a historic centre whose harmonious streets and buildings reflect a deliberate vision of urban design.

Set above the Val d’Orcia, Pienza is also closely associated with pecorino, its traditional sheep’s-milk cheese. Architecture and local food give the town two distinct expressions of place; the visit is included, while a cheese tasting is not specified.

Choose an optional excursion to Cortona, a historic hill town in eastern Tuscany. Its steep streets and elevated setting offer a different perspective on the region’s enduring small-town character.

Cortona’s heritage reaches back to the Etruscans, while its medieval buildings speak to later centuries of Tuscan life. This experience is at additional cost and bookable on tour; the supplied itinerary does not specify particular guided visits or admissions.

Choose an optional excursion to Lucca, a Tuscan city known for its intact Renaissance walls and atmospheric historic centre. The broad ramparts encircle streets, churches and piazzas that preserve the feel of an independent Italian city.

Lucca’s long history is visible in the layers of its urban fabric, from Roman-era street patterns to later fortifications. This experience is at additional cost and bookable on tour; specific guided visits and admissions are not detailed in the itinerary.