Sara Jane Stroupe

June 2023 Issue

by Edwina Hoyle
Photos courtesy of Sara Jane Stroupe

Sara Jane Stroupe was only four years old when she first traveled to Europe. Even at such a young age, Sara Jane remembers those childhood trips. Her grandmother, Bette Anderson, who is now 95 years old, was appointed undersecretary to the Treasury by President Jimmy Carter. She also served on the board of International Telephone & Telegraph (ITT), which owned Sheraton Hotels at that time. Sara Jane said every year ITT would hold their board meetings in Europe. Along with her Mom, Dad and sister, they would travel with her grandmother. Little Sara Jane got to visit Switzerland, England, Italy, France, and Germany.

One of her best memories of a trip with her grandmother happened in Switzerland. Bette grew up on a farm and wanted a big Southern breakfast. “We went to a McDonald’s, and of course, they didn’t have anything like that. And there was a language barrier. Growing frustrated, Bette got louder and louder as she tried to explain what she wanted, finally yelling out in English. So, we ordered her a croissant to quiet her down.”

These adventures with her grandmother planted a seed that would sprout into a passion for travel. Last year Sara Jane traveled to eight countries, and so far, this year, has been to Portugal, Mexico, Italy, and will soon go to Greece. Sara Jane’s two children, Hayes (age 4) and Hadley Kate (age 8), accompanied her to six countries last year.

Six years ago, she and her husband, Ryan, took Kate to Disney World for the first time. Sara Jane did a lot of research and planning to make it the best, most magical trip possible. Afterward, friends and family would ask her to help plan their trips to Disney World.

At one time, Sara Jane owned and operated a boutique children’s clothing store for twelve years. She studied fashion merchandizing at Ole Miss (University of Mississippi) always dreaming of having her own store. After graduation she took a job working for Dillard’s buying program in Dallas. Then she returned to Savannah and made her dream a reality.

Her passion for travel plus her side gig of helping families make travel plans led Sara Jane to accept an offer from a college friend to work in her travel agency on the side. Her business took off and six years ago she closed her store to become a self-employed travel agent for Cupcake Castles Travel Company. “My business grew so much it was making more money, and I got to spend more time with my kids. I went from luxury children’s clothing to luxury travel, melding my two passions.” The motto of Cupcake Castles Travel Company is to sprinkle magic, but Sara Jane likes to say that she prefers to sprinkle pixie dust. “I’m a bubbly person and like to make unique opportunities for families.”

As a professional travel agent, Sara Jane has opportunities to travel in order to become familiar with different resorts, hotels, and locales. “It’s important for your travel agent to travel to become knowledgeable about places they are recommending. It has its perks,” she said.

“I like to quote Walt Disney: ‘If you can dream it, you can do it.’ People always wait to travel with kids. They ask me when they should include children. I tell them whenever you’re ready, do it,” explaining that even small children will hold onto memories.

Sara Jane is also amazed by her own children. “At such young ages, kids can come together with other children. They can communicate even though they don’t speak the language. They come together, play together, and it’s amazing. I wish in this world that we adults could do more to understand one another and communicate better.”

“When kids experience different foods, different places, and things from history… it’s like a history lesson. You can learn so much outside a classroom,” Sara Jane said. “Getting out and experiencing different cultures opens your mind and gives you a different viewpoint. For some people safety is a concern, but there is danger right here in America today. Every trip you take, you come back a different person. You grow, you learn—it’s a form of self-care.”

So, what was Sara Jane’s favorite trip? She studied abroad while in college. She went to Australia and spent an entire summer exploring the whole country. “We toured resorts discovering each area to be quite different. You go from the jungle to the desert, to the ocean. It was so clean, and so safe, and everyone was nice.”

Up Close:

• Bette Anderson, Sara Jane’s grandmother, also served as President of the National Association of Bank Women (1976); managed a budget of $5 billion while in Washington; and introduced the Susan B. Anthony dollar coin (1979).

• Sara Jane and her husband, Ryan, have been married for nine years. Ryan chose Jamaica as their honeymoon location! Of course, this was before Sara Jane became a travel agent.

• Sara Jane has two different colored eyes: one is green, and the other, brown.

• Sara Jane’s family includes two yellow labs: Annabelle is 10 years old, and Millie is 3 months old.