The Makers Among Us: Annie Pezza
When most people return from a trip, they unpack their suitcase, scroll through a few photos, tell the same stories to family and friends and move on. Bluffer Annie Pezza wondered what happened to those stories after that. She believed they deserved a place to live. That idea eventually became Pinerary (a blend of the words pin and itinerary), a platform where travelers share the experiences that changed them and inspire others planning adventures of their own. “I didn’t realize this when we first launched,” she says. “I thought it was all about sharing travel.” It turned out to be something much bigger.
Today, Annie describes Pinerary as a community built on generosity, where travelers don’t simply post itineraries; they preserve memories that help someone else discover a place they may never have considered. “What we really want from you is your travel story,” she says. “We all have them.” Those stories serve as a lasting digital travel journal that can be revisited years later, shared with friends or even turned into a photo book. Just as importantly, they help someone else travel a little more thoughtfully.
“What we really want from you is your travel story,” Annie says. “We all have them.”
Starting Pinerary wasn’t easy. In fact, Annie calls it one of the scariest things she’s ever done. She first shared the idea with her husband, Paul, on their anniversary in 2018. While he was working toward his MBA, he encouraged her to take the leap. During the pandemic, Annie immersed herself in the travel industry, researching trends, reaching out to founders, networking and attending conferences but there were inevitable setbacks. After spending a year building the first version of the platform, the project fell apart. “I almost gave up,” she admits. Instead, new connections led her to a different development team, and Pinerary officially launched in July 2024. Building the platform in public has been intimidating. “It’s a community,” she says. “And when you build a community, it usually has to begin with your own.”
Paul, Annie, Francesca, Cole and Jeannie Pezza
Annie describes herself as a seeker. She’s the person who’s always curious about what’s behind the locked door or around the corner with the “Do Not Enter” sign. “That probably got me into trouble as a teenager,” she says with a laugh. “I’ve never been satisfied with a simple, ‘No, you cannot.’ I ask, I find a way, and I usually get my answer.” That curiosity has shaped the way she thinks about travel. She believes the most memorable trips aren’t defined by a checklist of luxury or tourist attractions but by the moments that stay with us long after we return home. “Pinerary is a home for those stories.” She also discovered an unexpected lesson after launch. At first, she asked friends to upload their itineraries. “It sounded like homework,” she laughs. She quickly realized that wasn’t what people wanted to share. Instead, they wanted to tell stories about the meal they still think about years later or the tiny café they stumbled across with the sweet owner. Pinerary takes those stories and turns them into structured itineraries that others can actually use. “I have hundreds saved,” she says. “Usually, it’s a combination of the destination, identifying with the traveler, the photos they shared and how the place impacted them.”
Like many entrepreneurs, she’s wrestled with self-doubt and imposter syndrome. She’s learned to let go of worrying about judgment and focus instead on the value she’s creating. “We’re celebrating some of the best moments of life,” she says. Her family reminds her how far she’s come whenever she begins to question herself. “They’re proud of me for doing something daring.” If Pinerary disappeared tomorrow, Annie says she’d miss the people most of all. The travelers, founders and overall hospitality community that has welcomed her along the way. “I learn every day,” she says. Whether she’s building a travel startup or someday greeting guests as a barista or restaurant hostess, the mission would stay the same. “I want people to feel seen and welcome.”