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.

We learned so much history about early Tokyo through the last shogunate and enjoyed the walk with Stewart even though the inner gardens were closed. It was really fun to put the city in its historical context!
Nick was a personable, friendly, and knowledgeable tour guide, whose knowledge of the history of Japanese food and drink was impressive and also accessible. He clearly knows his stuff. I would recommend him for a future tour, and both my son and I had a wonderful day in Osaka.
His enthusiasm is unmatched. He was flexible and asked about our preferences often. He knows so much about the Singapore food history and any other side question that you have. Be prepared for high energy from his explanations but there is waiting to eat while it is freshly prepared. It's hot walking around the city but he works too keep you comfortable. Dress lightly. The food was delicious and exotic to our US taste buds. Don't miss this experience where most of Singapore eats.... Clean, delicious and unique with a Michelin star at some spots.
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