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- Kayla Fagan
Kayla Fagan
Chesapeake, VA Travel Agent
Areas of expertise
Destinations:
Italy, Walt Disney World, DisneylandInterests:
Disney Vacations, Cruises, Christmas MarketsSuppliers:
Disney, Norwegian Cruise Line, Royal CaribbeanAbout Me
Independent Contractor
My love for travel started early, thanks to my parents. From Spring Break trips to Disney World to weeks-long road trips through National Parks, my siblings and I were lucky to explore much of the U.S. at a young age.
While completing my undergrad at Virginia Tech, I took a Travel and Tourism class, dreaming of becoming a travel agent one day. But life had other plans. A government job led me to my husband, an active-duty Air Force officer, and together, our adventure began.
As newlyweds, we spent three years in Northern Italy, making the most of our time abroad by visiting 30 countries—many of them on Norwegian Cruises. I naturally became the group’s travel planner, spending countless nights scouring booking.com and Skyscanner for the best last-minute deals. One of my most memorable trips was a road trip from Italy to Poland with my dad and sister along for the ride.
After our European adventure, my husband and I spent three years in the Mojave Desert, where we started our family and continued traveling as often as possible—weekends at Disneyland, road trips to Washington State, and even a getaway to Disney’s Aulani Resort in Hawaii.
In 2020, we returned to the East Coast, and like many, our travels paused due to the pandemic. After a brief 10-month assignment in Alabama, we are finally settled for the next three years in Chesapeake, VA.
Now, with our youngest turning two this spring, we’re excited to dust off our passports for our first family cruise this summer! After dreaming about it for over a decade, I finally took the leap in January 2025 and became a travel advisor with Destinations to Explore. I can’t wait to help families plan their dream vacations—whether it’s a magical trip to Disney World (our personal favorite!), a Caribbean cruise, or an unforgettable European adventure!
Areas of expertise
Destinations:
Italy, Walt Disney World, DisneylandInterests:
Disney Vacations, Cruises, Christmas MarketsSuppliers:
Disney, Norwegian Cruise Line, Royal CaribbeanCertifications & Awards

