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Trip Diary: On the Road

How one group of friends gets paid to travel


Rico bowls a frame at Nashville’s Pinewood Social, subbing bowling shoes for moccasins from one of their sponsors.

@getlostwith tinerary

Nashville: 3 days
Asheville: 1 day
Charleston: 6 days
Savannah: 1 day

By leveraging their photography skills and collective social media presence—nearly 50,000 combined Instagram followers—a group of San Diego creatives formed the Get Lost With Us project (@getlostwith), secured a few like-minded sponsors, and hit the road. Here, photographers Rico and Rachel Castillero; wedding planner Tori Hendrix and her DJ/filmmaker husband, Austin; and videographers Molly and Max Cutrone (plus three dogs and a toddler), share a few snapshots from their most recent trip, through the American southeast.

Scenic route

“Since we are all artists in some sense, we really value places that are interesting or beautiful,” Tori says of the group’s choice to visit cities with food and art cultures and to stay in unique properties they find on AirBnB instead of chain hotels.

Got recs?

Once they arrive in a city, the group crowdsources recommendations on where to eat and what to see from its Instagram followers, which led them to this tasty breakfast at Asheville’s Barista Parlor. Rachel says, “It’s definitely one of the best ways to travel.”


Baggage is good

“If you have children, don’t let that stop you from traveling!” advises Tori, whose three-year-old daughter, Lucca Valentine, tags along on the trips. (Her legs are pictured here, at a shop in Charleston.) “It makes them more adaptable little people.”

Go with the flow

“We all share the same travel philosophy, which is that we like to be flexible and experience the overall feeling of a city instead of doing touristy things,” Rachel says. “We love getting lost and embracing the unexpected.”


Get Lost With Us’ road trip playlist

“The Stable Song” by Gregory Alan Isakov
“Hey Mami” by Sylvan Esso
“Work Song” by Hozier
“Beth/Rest” by Bon Iver
“Ohio” by Patty Griffin
“Slow Love” by MØ
“Ghost Town” by Sam Outlaw

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