Chris Shelley: Exploring NYC, One Step at a Time

“New York is a city of possibility and endless exploration. There’s always something new to discover around every corner.” – Elizabeth Gilbert

Guest Introduction: 

Welcome to Exploring the Seasons of Life: Travel Edition. I’m Cindy MacMillan, your host and the owner of Pangea World Travel Agency, a boutique agency located on the Space Coast of Florida.

If you enjoy today’s episode, I’d love it if you shared it, left a review, or spread the word. Your support helps us inspire even more travelers to embark on their own adventures.

So, pour yourself a cup of coffee or tea, settle in, and let’s explore the world together—one incredible journey at a time.

Now, it’s my pleasure to introduce our guest today.

Chris Shelley is a licensed New York City Sightseeing Guide. He offers private walking tours through his company Walk With Chris.

He is also a Professional Wedding Officiant who has performed hundreds of ceremonies all around the country. His book Best Ceremony Ever, published by WW Norton, helps couples and wedding pros make ceremonies fun. He's a very social guy who loves his two very social, very unique jobs.

With his diverse experiences and deep love for New York City, Chris is sure to bring fresh insights and great stories to today’s conversation!

Here’s a glimpse of our conversation: 

Welcome to the podcast Chris.

1:58 I moved to New York City in 1992, right after graduating from Boston University, where I was part of a small acting conservatory. All 12 of us in the program moved to New York, hoping to make it in theater—or maybe even TV and film—since so much of the industry was based there. I was such a good actor that I ended up working on Wall Street.

4:40 My wife and I were in New Orleans, Louisiana, taking a walking tour with a local guide—something we love to do wherever we travel. We've done walking tours all over the world—Italy, Iceland, France, the Czech Republic, and many other places. But during this particular tour, I had a Eureka moment. I suddenly thought, Could I do this? It had everything I loved—social interaction, storytelling, even elements of stand-up and acting. I had always assumed you needed to be a history professor or an expert to lead tours, but in that moment, I started to see it differently.

9:35 When I take people to Rockefeller Center, St. Patrick’s Cathedral, Grand Central, and other iconic landmarks, that’s where I truly shine—I light up because I’m genuinely interested. Sure, I could learn a bunch of facts about different parts of the city, but without a personal connection, it just wouldn’t be as engaging.

14:56 Tourists often stick to the middle of Manhattan and rarely venture to its edges.

28:41 I’d take them to Rockefeller Plaza. Yes, it’s touristy, but it still feels like a unique and fascinating hub of the world. Unlike Times Square, it isn’t all about commercial glitz—it’s about the stunning architecture and the iconic sunken plaza. For part of the year, it’s a skating rink, but the rest of the time, it transforms into a space for art exhibits and picnic tables. It’s an incredible place with an energy all its own.

31:23 Rockefeller Center, the southeast corner of Central Park, and Washington Mews.

You can find Chris Shelley at:

Website | Instagram | Illuminating Ceremonies

Thank you so much for joining me on Exploring the Seasons of Life: Travel Edition. I’m Cindy MacMillan, and you can find me at PangeaWorldTravelAgency.com. If you enjoyed this episode—and I truly hope you did—be sure to hit the subscribe button so you never miss an episode.

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Until next time, keep exploring, stay curious, and take care!