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

81,019 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.

Tour was fun and we enjoyed ourselves. When it was over it would have been great to have had a list of the stops we made. I wanted to gioback to a few spots but it was impossible because we criss crossed and went all over in the dark and couldn’t reconstruct where we went. I also appreciated that right up front he light-heartedly set our expectations so we understood there was no guarantee we would actually see a Geisha. We did get lucky and had a few brief and one really up close sighting!
Gina was fabulous. She is a foodie’s foodie. Her depth of knowledge and warmth of heart shine well within her love of Italian and Roman history, food, wine and culture. We had a splendid, unhurried day immersed in such things that went all too fast. Steve & Mim
Photo Shared by Steve with their review
We really enjoyed our tour with Giacomo. He was really engaging and a wealth of knowledge about The Last Supper and Leonardo. He also included a beautiful church and a WW II artifact remaining on a building as we were walking about. We really appreciated the shopping and dining tips too! After our tour we had lunch at Peck. So delicious and we never would have know about the bistro inside.