On a hot September afternoon, I walked up to the visitors’ center of the historic Washington Monument — one of the most impressive structures in DC (which is a city of impressive structures in itself) — with my friend and fellow travel blogger, Leticia Barr.

Of course, Leticia took the opportunity to snap a selfie upon arrival.

There we met Jonny Grave, a journalist and guitarist (complete with long hair and aviators), who not only had substantial knowledge on Washington politics and history, but had grown up and lived in the city his entire life (he was also easy on the eyes, though you can see that for yourself in the video).

Jonny is a docent for Context Travel, which organizes private and small-group walking tours with expert guides in cities all around the world. It caters to the “intellectually curious traveler” – the person who wants to not just breeze through a new place, but rather truly understand its background, its culture, and even its current challenges.

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Taking Your Own Two Feet

If you’re like me, thinking about a tour brings to mind images of enormous charter buses, inauthentic meals, and limited wandering time. They’re not the most appealing to a globally minded, locally engaged travel lover.

Yet, there are other tours that can actually enhance your travel experience.

Small walking tours allow you to supplement your visit with information you may not have picked up otherwise, from someone who lives in the city, while also not feeling dragged along from point to point. Not interested in seeing the Baroque sculpture at the end of the rose garden? No problem – we’ll skip it.

Perhaps the best thing that a walking tour can give you, though, is a good grasp for a new place. There’s nothing quite like seeing a city with your own two feet, and with someone beside you who knows where they’re going.


They can help you identify things on a map to orient yourself. They can tell you how that crazy metro system works, or which bus lines are least likely to get delayed. They can give you the goods on that secret jazz club tucked between the pizzeria and the Thai restaurant that only the locals know about. And they can do that while also explaining to you the architectural history of the structure you are looking at right now.

It’s kind of like getting a quick orientation to your new place. Or having a friend join you for a couple hours to teach you the ropes.

Context Travel: Small Tours, Big Payoff

Thanks to a sponsored opportunity with Context Travel (view Wanderful’s disclosure statement here), Leticia and I got a taste of what a real Context tour is like.

Typically three hours, these tours involve no more than six people, so you can spend as much (or as little) time as you like in each location, ask questions to your heart’s content, and get to really know the person who’s taking you on this journey.

Plus, since they’re local, it’s a great opportunity to ask about favorite restaurants, bars, and other activities to do after the tour is over.

For a semi-private tour, the price point is appropriate. One ticket will cost you about $85 USD, which is very worth three hours of someone’s personal time, especially if you’re jonesing for a special activity like a unique bachelorette party or a honeymoon.

Of course, we wouldn’t be very good bloggers if we just experienced the tour for ourselves. So we took 400 of our favorite community members with us by broadcasting the whole thing on Facebook Live. This way, you can see a Context Travel tour before taking one. And if these tours are a total bust, you’ll be the first to know.

Courtesy of Leticia Barr.
Courtesy of Leticia Barr.

Spoiler Alert: We Had An Outstanding Time

On our National Mall Tour, Jonny told us why the Washington Monument is two colors (3:30), gave me one of my new favorite stories about Teddy Roosevelt and the invention of the teddy bear (29:50), and took us to the very spot where Martin Luther King, Jr. made his famous “I Have A Dream” speech during the 1963 march on Washington (43:30).

As someone who once lived in DC for two years, I had spent many an afternoon walking through the National Mall and gazing at its fascinating monuments, but never knew any of those things. Even Leticia (a local herself) was thrown a few surprises.

Take a look at the video above to watch the tour in full, or skip around for some highlights. If this is any indicator of the quality of Context Travel tours, this won’t be my last one.

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Have you ever taken a walking tour? Tell us about it in the comments!