Caitlyn Sipes

Caitlyn was raised on adventure thanks to her mom, Kimberly, and no stranger to the thrill of the unknown. Her childhood was filled with waterfall hunts, “left or right?” coin-flip road trips, and even the occasional hot-air-balloon chase.

By age 10, she was already navigating airports on her own, gaining real-world experience traveling as an unaccompanied minor both before and after 9/11. Over the years, she’s confidently tackled trains, buses, cabs, and airports all across the map. In high school, her explorations took her even farther: an Italian exchange program, sailing catamarans in the Caribbean, dog sledding through the Rocky Mountains and a helicopter tour over Maui, Hawaii, just to name a few.

As an adult, her travel style has evolved, mostly. Though her heart still belongs to spontaneous adventures, like that one New Years Eve spent at Epcot... She has learned that having a trip booked is the best motivation to get to work in the morning! :) 

When she isn’t on the move, Caitlyn calls Western Massachusetts home, where she lives with her son, Sam, and her partner, Mike. She works in accounting for a small town, funding her passion for exploring. Sam, a seasoned traveler himself, has flown across the country many times to visit family and has become a true little travel pro. One of Caitlyn’s biggest goals? Taking him to all 50 states before he graduates high school. Luckily, Kimberly and Reuben (dad) live just five minutes away, helping ensure that Sam grows up with the same sense of wonder and love of discovery that shaped Caitlyn’s own childhood.