Show up to a designated meeting place.

Locate tour guide.

Receive a heavy receiver and headset.

Join a crowd of 20+ people.

Attempt to keep up with said group through a fast-paced city.

Attempt to keep your interest in said tour guide’s pre-drafted spiel.

Clamber around said group to capture the perfect photo of the subject spoken about, but fail.

Leave never having spoken to your tourmates or tour guide, except a quick “thank you” and tip exchange.

Does this routine sound familiar?

I’ve been on countless city tours, both in the U.S. and abroad, and this routine is pretty much universal. While it is effective (and I’d be lying if I said I haven’t enjoyed many tours given in this format!), there comes a time in one’s travel career when you feel inspired to dig a little deeper.Exploring New York with Context Travel_15

Enter Context Travel.

Context Travel specializes in small-group tours (no more than 6 people – always!), led by Ph.D. and MA-level docents. These guides REALLY know their stuff and happily lead travelers into the heart of a city to explore the history, architecture and culture that gives it life.

Operating in 35+ cities around the world, Context provides travelers with a deeper view of your destination – often taking you off the beaten path of a traditional city tour.

A tourist comes to a city to snap some photos and check boxes off a list. A traveler comes to a city to mingle with its people, to taste the flavors of its cuisines, and to learn the history and struggle of those who made the city what it is today. It is the intellectual traveler, one intent on getting under the skin of a city, that would feel most at home on a Context tour.

I was fortunate enough to be invited to experience two Context tours on my recent trip to New York: History of Finance and Brooklyn: Portrait of a City.

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History of Finance

I showed up to meet my tour group for History of Finance, not quite knowing what to expect. My guide, Bill, made me feel at home right away. He introduced me to the two others (only two – this is fantastic!) that would be joining us, and we began winding through the streets of the Financial District and Wall Street.

As we went, Bill, shared stories with us about how New York rose to power as one of the financial powerhouses of the world. From our start seeing Alexander Hamilton’s grave at Trinity Church, and learning about his role in the creation of the first Bank of the United States, to visiting the New York Stock Exchange, there was a rich history behind every new site we visited.

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Bill, a former Wall-Streeter himself, brought his own personal history into the tour as well. He shared his favorite after-work haunts with us, showing us the popular restaurants and taverns for after-hours finance deals. As we ended the tour in front of the World Trade Center, he also shared his own personal story and take on 9/11 with us, which I found deeply moving. I had planned to head over to the Statue of Liberty after the conclusion of the tour, but after speaking with Bill about the World Trade Center and being so moved by our conversation, I chose to visit the 9/11 Memorial and Museum immediately after.

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Brooklyn: Portrait of a City

I was particularly excited to visit Brooklyn, as I’ve heard from many about what a colorful place it is. I joined my guide, Matico, an architectural historian, and four others, to dig into this incredible borough.

We started on the Manhattan side of the Brooklyn Bridge, where we learned about the methods architects used through the years to guard their buildings from fires. Then, we crossed the Brooklyn Bridge together, while learning how it came to be as a gateway between Manhattan and Brooklyn, as well as learning about the parts of its structure that make it unique.

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After crossing, we passed through DUMBO, a warehouse district turned trendy gallery neighborhood, and into Brooklyn Heights. Brooklyn Heights is the area directly across from Manhattan and features stunning views of the city. We wound through the neighborhood snapping photos, while Matico pointed out the nuances of the brownstones lining the streets, many featuring different architectural styles. Our tour ended in front of the Brooklyn Historical Society, a building adorned with beautiful depictions of scholars and historical figures.

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Thoughts on Context

I originally thought Context would be just another tour experience. However, I was so surprised by the in-depth knowledge our tour guides had. Our guides weren’t reading off a script – they were genuinely interested in and excited about the information they shared with us. They didn’t seem frustrated or put-out by travelers asking questions, as I’ve experienced on other tours. Instead, they reveled in sharing their knowledge with us.

My favorite thing about Context, by far, was that I felt as if I was exploring the city with a group of friends, not a tour group. I kept pace with my guides and fellow tour-goers. We made jokes, asked lots of questions, made bathroom stops (usually not possible on bigger tours because of the sheer number of people), and took detours. Rather than sticking to a mapped-out route, our tour guides took us to different spots in the city, based on our interest areas and the questions we asked. We were able to bond with each other in a way that isn’t usually possible on larger tours.

For those looking to dig a little deeper into a city and see beyond the typical tourist attractions, I highly recommend booking a Context Travel tour. You’ll make new friends, explore places you wouldn’t see normally, and learn from someone who genuinely knows their stuff.


See more from my adventures in New York here:


What’s the best tour experience you’ve ever had? Let me know in the comments below!

Disclosure: I joined the History of Finance and Brooklyn: Portrait of a City tours as a guest of Context Travel. The tours were a gift, but as always, all views and opinions expressed here are my own, based on my personal experiences on the two tours.