Filming crew on location

We Were on NBC's 'New York Live'!

Watch me take 'New York Live' on a surprise road trip!

Last summer, I packed my bags, hopped on a plane to NYC, and joined host Lauren Scala for a surprise road trip adventure along the Delaware River.

Our day perfectly captured what Guess Where Trips is all about: the thrill of the unknown, the joy of discovery, and the magic of supporting local businesses in your own backyard.

How the opportunity came up:


This whole adventure was months in the making! The NBC team and I went back and forth coordinating schedules, logistics, and timing.

But the second I got the green light that we were actually doing this? I booked my flight immediately.


I brought along my best friend Olga (from @minijetsetter) who became the unofficial behind-the-scenes documentarian of the day. We've traveled a lot together over the years, but it was so special to share such a major business milestone with her.



Jess with the New York Live crew!

❗️ Spoiler Warning

The video below highlights some of the stops on our surprise trip from New York City and Philadelphia, Along the River. If you live in the area and want to be surprised, maybe skip this part...

The Best Kind of Road Trip Companions


Lauren and the New York Live team were incredible! Their energy, curiosity, willingness to just trust the journey was so appreciated on a day that could have been overwhelming! They got it immediately, and we couldn't have asked for a better road trip crew.

Fun Fact: Despite traveling in early June, is was 88° and we were all melting. A lot of iced coffee was consumed, makeup was constantly reapplied, and we became very strategic about finding shade. 

When I started Guess Where Trips over six years ago, I never pictured this. Being on TV in New York City. Features in newspapers across the country. Sitting down with journalists and hosts to talk about uncovering hidden gems and the magic of supporting small businesses. And yet, here we are.

But here's what I've learned: when you build something that genuinely helps people rediscover joy in their own backyards, when you champion small businesses that make our communities special, and when you take the stress out of planning so people can focus on the memories, people notice.

Thank you for trusting us with your weekends!

Jess with the New York Live crew!
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