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

81,094 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.

I walk slowly with a cane. When I saw the size of the Uffizi I was concerned how I would keep up. The guide suggested that a wheelchair would be available to borrow. It made all of thew difference. I was able to enjoy my tour as was my friend and the guide because I didn't slow everyone down and I could concentrate on the exhibits.. I was so appreciative!
So much information, we learned so much! Thank you!
Liz gave us her undivided attention, professionally navigating us through the overwhelming crowds to well-selected viewpoints that allowed her to share her wisdom in a calm and normal tone. Liz never gave us the feeling of being rushed, and paced the information and the distances perfectly to suit our energy levels. I would highly recommend Liz and her broad insight on Roman life and Italian architecture was superb! Coincidentally, we just realized Liz was the same Context guide hired by our Aunt and Uncle almost 10 years ago - we just discovered this recently as we recalled our separate trips to Rome - and figured out it was the SAME Liz!!