Italy Private and Small Group Walking Tours
Home to many of the world’s greatest works of art, architecture, and gastronomy
The cradle of European civilization, Italy has often been described as one big living museum. As you explore the country, you’ll find yourself face-to-face with some of the world’s most influential thinkers and artists throughout history.
"Alessia is a very knowledgeable guide. We had a great discussion with her from religion to culture during the trip. She has left a deep impression on us, and made our trip in Rome so memorable!" – Sherry
Rome
Hit the highlights and then venture further into the Eternal City
Florence
Birthplace of the Renaissance
Venice
Where Architecture Dances on Water
Naples
Complex Neapolitan Soul
Sicily
A Rich, Diverse, and Vibrantly Scenic Historical Land
Milan
Fashion Capital
Lake Como
Italy's Timeless Retreat
Siena
Medieval Marvels and Wine Tasting
Lucca
Historic, Medieval Charm
Pisa
The Leaning, Historical, Architectural Gem of Tuscany
What Context Italy Travelers Say
–
23,620 Reviews
Reviews can only be left by Context customers after they have completed a tour. For more information about our reviews, please see our FAQ.
We really enjoyed our Introduction to Venice Tour with Emanuele! He was very informative and helped us learn a lot about the History of Venice as well as specifics about St. Mark’s Basilica. The lace of our tour was excellent! If you get the chance, this tour will not disappoint.
Dan
Mar 24, 2025
Olivia was incredible! We enjoyed her so much, her love for art and history, stories where fun and memorable, she kept two teens fully engaged and answered all or our questions. This tour made us feel like we were VIP. The best part about Olivia is we ran into her another day at another sight and she engaged with us and helped us navigate a different spot. This tour was recommended to us from a coworker and was something we spent the extra funds towards and so happy we did. Thank you, Olivia we will remember your insights for a lifetime! April, Josh, Georgie and Keegan!
April
Mar 24, 2025
Matteo was so knowledgeable, thoughtful, and did a wonderful balancing act between providing knowledge and entertainment for our children and for us. He really made our trip special!
Victoria
Mar 24, 2025