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.

Anthony was an excellent tour guide. He was knowledgeable about culture and history, well-prepared with images and stories, and flexed the day to suit our private group’s interests and energies. A very nice person with whom to spend the day - many thanks for a hugely enjoyable tour, Anthony!
The Valley of the Temples is nothing short of magical! Our guide, Salvatore, with his incredible knowledge of history, archaeology and Sicily made the two hours fly by. We learned so much and thoroughly enjoyed our time with Salvatore!
Our tour with Giulia was another great Context tour! She was super knowledgeable about the history of the art in the Vatican and how to navigate the crowds. She prepared us for what we would see in the Sistine Chapel in terms of the art, but the surprise was witnessing a marriage proposal!
Photo Shared by Lisa with their review