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

80,991 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.

Adam was absolutely wonderful! He made our trip to the Prado so enjoyable with his intimate knowledge of the museum, artists, and paintings. He always included our 12 year old son in the discussion and made the tour so fun. We would not have had the same experience had we gone to the museum on our own. I would 100% recommend booking a tour with Adam!
Miyo planned a perfect tour catered to our individual needs. She met us at our hotel instead of the Dotonbori which was hectic and crowded. She asked good questions to try to get to know us and was sincerely interested in our lives. Her English was perfect and easy to communicate.
Photo Shared by Pat with their review
We enjoyed the tour very much. We were renting an apartment in the Cannaregio sestiere and, since Elena lives there, she was able to give all kinds of helpful hints (great bakery, produce stand, etc.). We’ve been in Venice before, but she provided plenty of new information. She was fun, entertaining and knowledgeable all at once. Very highly recommended!