Going Places: A Conversation with Chari Chin-Young Caston

By Amanda Wowk

November 23, 2022

Going Places is a new series from TripIt that highlights frequent travelers to showcase their unique travel styles and insider tips. 

Growing up in Queens, New York, Chari Chin-Young Caston knew she was living in the heartbeat of the U.S. But, thanks to many trips to her parents’ native Jamaica when she was young, as well as her time in France and Spain during college, Chari’s eyes were opened to what being a citizen of the world could mean. 

In 2015, Chari and her now-husband both quit their jobs and embarked on a two-year backpacking journey through Asia. 

“That trip changed my life—my whole perspective—and made me want to remove material things, shift priorities, and reconsider: ‘what do I really want?’” Chari said.

Ultimately, that trip inspired her mission: to spend her time helping others experience the world like she has. In addition to being an entrepreneur, content creator and mom to daughter, Zen, Chari is the co-founder of World Peace Connection, a non-profit organization with the goal of connecting people with service missions around the world. 

Chase deals, not destinations 

So, what does a day in Chari’s life look like? 

“By day, I’m a budget travel strategist. I help people plan the trips they don’t think they can afford to take,” she said. “My motto is: ‘Chase deals, not destinations.’ And that starts with knowing your budget—and then building out your itinerary from there.” 

A top tip? “Know your geography!” she quipped. “If you’ve always wanted to visit Spain, but you saw a great flight deal to Portugal, why not visit both—and save money in the process?”

She also advised to pack light to save on checked-bag fees. “I only bring a small backpack on trips. Four outfits? That’s plenty.”

Tip: Follow Chari on Instagram for tips for saving money on flights, packing light, traveling with a toddler, and much more.

As for the travel tool she can’t live without? “TripIt! I love the app for keeping all of my plans organized,” she shared. 

“I also rely—heavily—on the TripIt blog to source ideas for where to travel next; for me, and my clients. I especially love the City Break guides. They save me so much time in my research process.” 

Get inspired like Chari: Check out our City Break guides.

On getting lost—and finding yourself 

When it comes to her personal travel style, Chari likes to balance planned activities (that she keeps track of in TripIt) with time to be spontaneous. “It’s something I love about travel that others seem to hate: The feeling of being lost.”

And for Chari, that can mean physically—or emotionally. “Travel is not just about the experiences you have when you’re in a new place. It’s also an opportunity to learn more about yourself—to figure out who you are when you’re in a faraway place.” 

So, what faraway places have meant the most to her? “Ghana. I loved learning about the richness of Ghana, and discovering its beautiful landscapes, waterfalls, and beaches. As well as Portugal—I would love to go back and share it with my daughter when she’s older.” 

Her final tip? “Travel with all of your senses. And if you can’t plan a trip right now, remember that you don’t have to be on a plane to travel the world. Talk to your neighbors. Get on YouTube. Be curious. That’s what travel is truly about.” 

Catch up on all Going Places features to learn new travel tips, discover underrated destinations, and more.