See the Church of St. Mary of the Angels in the valley, then explore Assisi’s cobbled medieval streets with a Local Expert. Step inside the Basilica of St. Francis, the monumental church built in honour of the saint.

Set on the slopes of Mount Subasio, Assisi retains stone lanes and churches closely tied to Franciscan history. The basilica’s 13th-century frescoes, including works associated with Giotto, mark an important development in European painting and lend depth to this hill-town visit.

Insight Vacations

• 5 Dinner (D)
• 10 Breakfast (B)
• 1 Lunch (L)

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

• Vatican City: Visit the Vatican Museums and witness the genius of Michelangelo in the Sistine Chapel.

Meet your Travel Director and fellow small-group travellers over dinner at a local Roman restaurant. Taste specialities associated with Lazio while getting to know the people who will share your journey through Italy.

Rome’s cooking draws on ingredients and recipes long associated with the city, from pecorino and guanciale to artichokes when in season. The meal offers a welcoming introduction to Roman food traditions in a neighbourhood restaurant setting.

Explore the Vatican Museums with a Local Expert, moving through galleries that hold centuries of art and craftsmanship. Enter the Sistine Chapel to see Michelangelo’s painted ceiling, and view the exterior of St. Peter’s Basilica.

The chapel remains the setting for papal conclaves, giving its celebrated frescoes a living role in Vatican history. With expert guidance, the artworks become part of a wider story of Renaissance ambition, religious patronage and artistic achievement.

Discover Rome’s archaeological heart with a Local Expert, seeing the Circus Maximus, the Arch of Constantine and Palatine Hill before visiting the Colosseum with a Local Specialist.

Hear how chariot races drew vast crowds to the Circus Maximus and how imperial victories were commemorated in stone. Inside the Colosseum, consider the spectacles that filled this first-century amphitheatre and the enduring place it holds in the story of ancient Rome.

Savour a dinner of Tuscan flavours and local wine at a restaurant in Florence. Share the table with your fellow travellers and discover the region’s approach to cooking through dishes rooted in local produce and tradition.

Tuscan cuisine is known for allowing straightforward ingredients to speak for themselves, while its wines reflect a landscape of vineyards and hill towns. Dining in the heart of Florence brings those rural food traditions into the setting of a Renaissance city.

Walk through Florence to admire the marble-clad cathedral, bell tower and baptistery, including the recreated Gates of Paradise. Explore Piazza della Signoria, where statues stand before the Palazzo Vecchio in the city’s historic civic centre.

The square has been a stage for Florentine political life for centuries, while its sculpture makes it feel like an open-air gallery. The walk reveals how medieval streets and Renaissance art remain woven into the city’s everyday life.

Choose to visit Florence’s Accademia Gallery and stand before Michelangelo’s David. See the monumental sculpture at close range, from its carefully worked anatomy to the poised expression that gives the figure its intensity.

Carved from a single block of marble in the early 16th century, David became a powerful emblem of Florence. This is one of two included Insight Choice experiences; the alternative is a walk with your Travel Director to sample a local Italian treat.

Choose to walk with your Travel Director to a local Florence favourite and sample a classic Italian treat. Hear how it became part of the area’s food culture while enjoying a taste of something residents return to time and again.

The short walk offers a more informal way to experience Florence, through a familiar local setting rather than a gallery. This is one of two included Insight Choice experiences; the alternative is a visit to the Accademia Gallery to see Michelangelo’s David.

Explore Pisa’s Square of Miracles during an orientation with your Travel Director. See the cathedral and baptistery, and admire the famously tilted Leaning Tower of Pisa, built as the cathedral’s freestanding bell tower.

The ensemble brings together some of Italy’s most recognisable medieval buildings in a broad, open square. Look closely at the marble details and colonnades as your Travel Director introduces the landmarks; the experience is an exterior visit, not a climb of the tower.

Glide through Venice by private boat past churches and waterfront palaces, and explore the city’s streets and squares with your Travel Director. See St. Mark’s Square and Basilica, the exterior of the Doge’s Palace, the Bridge of Sighs and the Rialto Bridge.

Venice was shaped by centuries of maritime trade, visible in its grand facades and canal-side architecture. Travelling by water and on foot reveals two sides of the city, from its ceremonial landmarks to its maze of smaller passageways.

Ride a gondola through Venice’s canals as your gondolier steers beneath bridges and alongside historic buildings. From water level, take in details of the palaces and narrow waterways that are easily missed on foot.

Gondolas have long been part of Venetian life, their slender shape suited to the city’s intricate canal network. The gentle movement of the boat offers a distinctive perspective on a place where water is both a thoroughfare and part of the city’s character.

Visit a Venetian glassblowing workshop and watch expert artisans shape heated glass by hand. Observe the precision needed to turn a molten material into delicate finished pieces, and hear about the techniques behind the craft.

Venice’s glassmaking heritage reaches back centuries, with its traditions closely associated with the lagoon. Seeing the artisans at work makes the skill tangible: each controlled movement depends on knowledge passed between generations and preserved by workshops still practising the craft.

Visit Casa Barone on the slopes of Mount Vesuvius, a family-run farm growing rare Piennolo tomatoes. Learn about its low-impact cultivation methods and taste produce from the surrounding land during a farm-to-table lunch.

Piennolo tomatoes have been cultivated around Vesuvius for generations and are prized for their place in local food traditions. By continuing to grow this variety, the farm helps preserve agricultural biodiversity as well as the flavours of the Vesuvian countryside.

Cross the Bay of Naples by boat to Capri, arriving at Marina Grande beneath the island’s steep slopes. Ascend to Capri town and explore its winding lanes with a Local Expert, passing whitewashed houses, cafés, boutiques and artisan studios.

Capri has attracted visitors since Roman times, including Emperor Tiberius. Between its close-set streets and views across the Tyrrhenian Sea, the guided walk reveals both the island’s long history and the coastal setting behind its enduring appeal.

Walk through Pompeii with a Local Expert, following ancient streets past the remains of homes, shops and public buildings. See the Forum, once the city’s civic and commercial centre, and examine the details that illuminate daily Roman life.

Mount Vesuvius buried Pompeii in ash during its eruption in AD 79, preserving an unusually detailed record of the town. Expert commentary connects its surviving spaces with the people who lived and worked there nearly two millennia ago.

Enjoy dinner at a Roman restaurant with Italian cuisine and wine, accompanied by a private performance of well-loved Italian music. Listen as opera favourites and familiar melodies bring a live musical dimension to the meal.

Italy’s vocal traditions have long filled theatres and gathering places alike. Hearing these songs performed at close quarters offers a different kind of cultural encounter, pairing the sound of Italian music with the convivial atmosphere of a shared table.