private walking tours

Experiences Guided by Curiosity

Where will your curiosity take you?
(4.81)
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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

Ways to experience Context

Private Tours

Just you, an expert, and your travel companions

Small Group Tours

Connect with other travelers

Audio Guides

Explore the city at your own pace

Pre-Trip Lectures

Inspire future travels and learn before you go

Excursions & Day Trips

Venture out a little farther

Tours for Kids

Perfect for young, curious travelers

What our guests are saying

81,097 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.

Mayukmi is an outstanding guide. She is extremely knowledgeable and presented information to us in a very understandable manner. She tailored the tour to our interests. We learned a lot and had a great time. Thank you for enhancing our understanding of the history and culture of Japan tour the tour of the national museum
We very much enjoyed our day with Marc. He is truly an encyclopedia of Japanese history, particularly as it relates to Kanazawa. We did a lot of walking through different districts and Marc shared lots of information regarding different classes of people, including samurai and geishas and how they all related to one another. The pacing, for us, was quite good and we appreciated his sharing how his personal experiences influenced his tours. All in all, we had a very enjoyable day and look forward to contacting him again when we make our way to Kyoto.
We had a great time with our food tour. John is a lovely person and tailored the experience well for us. He took us to lesser-known areas to try great options. His background in food safety also added much information to the culinary adventure. Lots of fun choices throughout the tour. We particularly enjoyed the final yakitori experience at a very local location upstairs in the middle of everything. You could tell this was frequented by locals and not tourists. Overall, we had a great time and would highly recommend John and this tour to anyone who wants a balanced evening of education and great foods.
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