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Italy

Expert-led Italy guided tours that turn art, history, and regional identity into meaningful discoveries.

Dive into Italy

Discover These Cities

The land of republics and renaissances awaits... Where will you go?

Bologna

Historic Italian city with medieval towers, long porticoed streets, rich food culture, and Europe’s oldest university.

Rome

Walk streets where emperors, popes, and republics left stone and story in every piazza, shaping Rome’s timeless civic life.

Florence

Renaissance patronage shaped Florence, where Michelangelo, Dante, and the Medicis left a legacy of art, culture, and ambition.

Venice

Canals usher you past palazzos and secret calli in Venice, where waterborne life and artistic legacies define every turn.

Naples

Alleyways open to lively piazzas where opera, Neapolitan song, and globally loved pizza reflect Naples’ spirited cultural energy.

Sicily

Sicily’s rugged landscapes, baroque towns, and ancient ruins reveal a Mediterranean island shaped by millennia of migration.

Milan

Futuristic meets Gothic in Milan, where fashion houses, art galleries, food and architecture converge in Italy’s design hub.

Lake Como

Glacial waters frame villas and footpaths around Lake Como, where Alpine hills and Roman legacies invite timeless exploration.

Siena

Siena’s winding brick lanes, Gothic palaces, and bustling piazzas reveal a city steeped in rich medieval character and history.

Lucca

Walls encircle Lucca’s cobblestone lanes where towers, promenades, and piazzas reveal the intimate charm of medieval Tuscany.

Pisa

Leaning monuments draw eyes upward in a compact city where medieval ambition and architectural quirk meet on the Piazza.

Verona

Historic northern Italian city with Roman ruins, winding medieval streets, the Arena amphitheater, and layered heritage.

Arezzo

Historic Tuscan city with medieval piazzas, Renaissance masterpieces, artisan workshops, and a long tradition of antiques and craft.

Genoa

Medieval streets descend toward a historic port where maritime trade and palazzi reflect centuries of Mediterranean commerce.

Let Your Curiosity Shape Your Journey

Join passionate experts on intimate walking tours that reveal a city's unique stories, spark conversations, and leave you seeing the world—and yourself—a little differently.

Experts, not guides

Explore with 1,200+ Experts, from historians and architects to chefs and archaeologists.

Crafted for conversation

With fewer than ten guests, engage your Expert through questions and immerse fully.

Structured, never scripted

Your interests guide your Expert, leading to stories and perspectives that matter to you.

Curious or connoisseur

First-time visitor or seasoned explorer, our tours span city highlights to deep-dives.

Expertly Led,

Personally Delivered

“ What I love about Context is the flexibility in a tour's itinerary: not only to satisfy our guests’ requests or needs, but especially to renew my interest and my passion for this fantastic town. ”

Italy, Seen with Context

Italy isn’t just a collection of iconic cities. Travel with an expert to discover how art, power, and regional traditions shaped a culture that continues to influence the world.

Hear from our customers

26,621 Reviews

Cesare is an exceptional guide. We benefited from his knowledge and love of Michelangelo and Leonardo da Vinci. It was a privilege to see Michelangelo’s Rondanini Pieta and da Vinci’s Last Supper with Cesare as he enhanced our understanding of these great works of art.

Photo Shared by Randal with their review

Priscilla is a wonderful guide - knowledgeable, humorous, and kind. We so appreciated the information she imparted and the historical context she provided. Highly recommend Priscilla!

Our tour guide Cecelia was excellent. She was so knowledgeable, pointing out details, telling stories or historical background of paintings, sculptures, altars, as we walked around. Both the Basilica and chapel are absolutely beautiful and brought a special feeling as we walked around. Thanks so much for the tour!

Photo Shared by Kathleen with their review