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

81,088 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.

Aline was an engaging, knowledgable, and personable guide. We all loved her and were totally enjoying her tour. Too bad there was a bomb threat in the Musée d'Orsay and we had to leave the building which was then closed for the rest of the day, half-way through the tour. Aline took us outside and then to a typical Parisian cafe to wait, and was able to get our coats back for us after we finished. You could tell she felt terrible about the interruption and closure. We would definitely take another tour with Aline.
We had the most incredible experience on our tour with Fedra. She was everything you could hope for in a guide—knowledgeable, kind, impressive, fun, and so personable. She took us to the most amazing places and shared interesting insights that brought everything to life. Her tips were spot-on and made the rest of our trip even better. Fedra’s warmth and energy made us feel like we were exploring with a good friend who happens to know everything about the area. We truly loved our time with her and can’t recommend her enough!
Photo Shared by Caitlin with their review
What a fun enjoyable adventure!
Photo Shared by Dixie with their review