Kaitlyn Kelley

My Story

Meet Kaitlyn Kelley – Your Personal Travel Enchantress ✨

Kaitlyn has always believed in the magic of storytelling, adventure, and a little pixie dust. A lifelong Disney fan and proud Ravenclaw, she first visited Walt Disney World at 18 and instantly knew she wanted to help others experience that same spark of wonder. While she may not be an official Disney Princess, she wears her crown and tutu proudly—especially when exploring the parks with her own crew of magical companions.

At home, Kaitlyn’s world is filled with imagination and laughter. She’s married to a brave Gryffindor and mom to two boys—a clever Slytherin and another fearless Gryffindor—who share her excitement for every adventure, whether it’s casting spells in Diagon Alley or sailing the high seas. For the Kelley family, travel isn’t just a vacation—it’s a way of life. In fact, it’s even become their favorite Christmas gift tradition!

Over the years, Kaitlyn has traveled in nearly every way possible—solo, with friends, as a couple, while pregnant, and with little ones in tow. She’s even coordinated large group adventures, including taking 19 family members on a cruise—because she knows that the best memories are the ones shared. That firsthand experience gives her the unique ability to anticipate her clients’ needs and craft truly personalized itineraries for every kind of traveler.

Clients often say that Kaitlyn makes trip planning feel just as fun as the vacation itself. Her approachable, easygoing nature and deep knowledge of destinations take the stress out of planning, allowing her clients to relax and actually enjoy the process. From the first idea to the final details, she’s there every step of the way—making sure every experience is seamless, special, and sprinkled with a little extra magic.

Whether you’re dreaming of Disney, craving the thrill of Universal, setting sail on a family cruise, or exploring tropical islands and historic destinations abroad, Kaitlyn is dedicated to making your journey effortless and unforgettable. Her goal is simple: to ensure every client feels confident, cared for, and ready to have the most fun, magical adventure possible—because she truly believes anticipation is half the fun.

Happy Clients

"I have always been a Disney fan since birth! The princesses were my all time favorites of course as well as other movies. Disney has changed my life in so many ways and may sound weird but the music has been there for me in tough times. Fast forward gave birth to my own princess and all I ever wanted for her was to be herself and love herself. Disney had taught her more than just life lessons. One day while scrolling on Facebook I came across Kaitlyn and her beautiful family having the most amazing time and I said I need to be next. I was led to Kaitlyn with second story travel and the rest was history!. She did EVERYTHING FOR ME! Booked my Disney Cruise that was AMAZING! Kaitlyn answered each and EVERY question I had day or night, made sure everything was set and told me everything I needed to prepare my travel. Sent over every piece of paperwork that we needed plus fun activities for our daughter to do during the cruise in spare time (not that we had much of because there were so many activities she told us about haha) we are truly grateful for this experience because of Kaitlyn we couldn’t be anymore grateful! Thank you sooo much again for everything you have done for me and my family. You made one of my dreams come true! Definitely will be booking again very soon!"
-T Jenkins