private walking tours

Experiences Guided by Curiosity

Where will your curiosity take you?

Holiday Magic with Context

Picture yourself wandering Vienna’s Christmas markets, snow falling softly, as a historian shares the wild imperial tales behind every steaming mug of glühwein. Or slipping into a tiny Naples workshop where an artisan shows you how they’ve been crafting those glowing nativity scenes for generations.

That’s the magic of diving into a Context holiday tour. No loud groups, no scripted lines. Just you, a ridiculously knowledgeable local expert, and the kind of stories that make you forget the cold. 

Whatever lights you up—art, history, food, architecture—we’ll match you with the perfect guide who turns twinkling lights into stories you’ll retell every December for the rest of your life.

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holiday tours with context travel

Deep, Engaging, Tailored: The Tour for Everyone in Your Party

Conversations, not umbrella tours

"Tim was great. Knowledgeable. Cheeky. Motivating. It was a wonderful tour. We could have talked for hours. This is the exact reason small groups are the best. One on one, non scripted information from a dedicated and knowledgeable professional. Thank you, Tim."

William L.
London, UK

Experts, not guides

“William literally writes the book(s) on the D-Day memorials which led to an incredibly informative day tour. From age 77 to 11, we were all captivated by his knowledge and his ability to connect the dots.”

Carolyn B.
Normandy, France

Tailored, not one-size fits all

“Fantastic way to learn or refresh your understanding of key aspects of the history of Britain... One of the great things about a Context private tour is your guide. You can tailor your experience to your group's individual interests. This was our third Context tour. We are 3 for 3 in terms of top shelf guides, each very knowledgeable and personable. Highly recommended!"

Owen M.
London, UK

What our guests are saying

81,063 Reviews (4.81)

Reviews can only be left by Context customers after they have completed a tour. For more information about our reviews, please see our FAQ.

Our walking tour with Eric was extremely informative and very enjoyable. He pointed out so many details that we would have missed and explained such a lot about the history of the area and all the different aspects of Buddhism. He patiently answered all our questions too! A really great introduction to Kyoto and would highly recommend to anyone coming here for the first time.
Photo Shared by Sharon with their review
Michael was a wonderful guide and a fountain of knowledge. Mr Middle Ages. Great tour of Noter Dame, Cluny and surroundings.
This was a very special experience, one we will remember with gratitude for many years to come. Eric provided a lot of detailed information about Geisha culture, and our time at the tea house was amazing. He and the maiko and geiko were wonderful at answering our many questions. Throughout, the women were beautiful, with a grace we don't usually have the fortune to experience. Playing a traditional game with them was a nice contrast - we all laughed together, and the warmth and humanity of that encounter truly touched us.