Kayla Fagan, Travel Agent in Chesapeake, VA

Kayla Fagan

Chesapeake, VA Travel Agent

Kayla Fagan

Chesapeake, VA

Kayla Fagan Photography and Travel, an independent agent with Destinations to Explore, a Travel Leaders Network Affiliate Agency

Areas of expertise

Destinations:

Italy, Walt Disney World, Disneyland

Interests:

Disney Vacations, Cruises, Christmas Markets

Suppliers:

Disney, Norwegian Cruise Line, Royal Caribbean

About Me

Independent Contractor

Disney World 2025 with my favorite travel buddy!
Disney World 2025 with my favorite travel buddy!

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!

Certifications & Awards

NCL University - Master's Degree
NCL University - Master's Degree
Seacademy - Violet Certification
Seacademy - Violet Certification