Travel expert Annie Pezza started as one woman who dreamt of finding a better way to travel. With a goal of bringing people together to share their travel experiences in a real way, Pezza formed Pinerary.

When I incorrectly guessed the name came from a combination of Pinterest and itinerary, Pezza told me I was not alone in that thought. The real story behind it is more interesting, but I’ll leave that for the Talking Travel interview.

What matters more, though, is what Pinerary is. It is a platform where people can go to see peoples’ experiences on trips. A clearer picture arises from more shared experiences. With thousands of visitors monthly, Pinerary is developing a large database of destination experiences.

Pezza discussed working with hospitality and travel brands to collect the user-generated stories, but she states it will never be a paid situation. While she said Pinerary will integrate AI into the platform, it will never be at the authenticity of the experience.

One other thing I like about Pezza was the first thing I learned about her travel mindset. Pezza stated the best part of a trip is being in bed on the first night. All of the major planning is done and it is time to just enjoy.

Raised in Denver, Pezza married a Chicagoan and resides there now. I took the opportunity to get her thoughts on some Chicago favorites.

Before ending our interview, Pezza told me there are a few new things in the works for Pinerary, but she couldn’t discuss them yet. That means a return Talking Travel interview will be needed in the future.

Talking Travel is an interview series on Global Traveler. Subscribe to the GT YouTube channel to be notified of all future interviews and other travel-related videos.

— John Wroblewski, podcaster