Wishful Wanderings: Heather Wilkinson finds her calling and a career in travel-planning

Heather Wilkinson has always had a knack for planning.

But it was a trip to Walt Disney World with her family that unexpectedly transformed it into a passion and a career.

“Our son was stillborn, so my husband and I were looking for a place to go with our daughter. She’s a Disney princess, and I love Disney, so naturally, we picked Disney,” said the 43-year-old, who relocated to Dubuque from Michigan with her family in 2014. “I’m a planner by nature, and we ended up having an amazing time. After our trip, I had friends coming to me, asking me to help them plan their trips. I thought, ‘This is something I really enjoy.’”

Deciding to leave the healthcare industry, Wilkinson began working for a local travel agency. But amid the COVID-19 pandemic — and wanting to help individuals return to travel safely — she took a leap of faith, striking out on her own and launching Wishful Wanderings Travel.

Established in October 2020, what began as a team of seven — many of whom followed Wilkinson from the previous travel agency — has grown to 28 women (in addition to a husband-and-wife travel-planning team), with agents located throughout the United States.

Led by Wilkinson and continuing to be based in Dubuque, the company specializes in Walt Disney destinations, Universal Studios, Royal Caribbean, cruises, Caribbean locations, and domestic and international travel for a multitude of occasions, with each travel agent specializing in specific locations.

“We help people plan for everything, from quick weekend getaways to Chicago to longer excursions abroad, destination weddings, family trips, reunions, guided group travel, you name it,” she said. “There’s obviously a lot of tools for people to use through the internet and A.I. to book trips. But in working with experienced travel agents, we are in-the-know about the best deals, travel trends, travel restrictions, how to pack. When something happens with your flight, we’re the first ones on the phone, making sure we’re getting you to where you need to be and within your budget.”

In the years following the COVID-19 pandemic, Wilkinson said global travel has continued to surge.

According to the U.S. Travel Association, the travel industry experienced 1.52 billion travelers in 2025, marking a 4% increase from the previous year and officially signaling a return to steady, pre-pandemic growth trends.

This trend is projected to grow another 3% to 4% throughout the course of 2026.

For summer travel, Wilkinson said Disney destinations always will remain popular among families but added that cruises and visits to national parks also are top travel picks.

Alaska, among Wilkinson’s specialties, is another location of which she is particularly fond.

She also added that a trip to Europe should be on everyone’s bucket list.

“People love pre-planned, all-inclusive travel because it takes so much of the guess work out of it for you,” she said. “These days, people are investing more in it. They want less stuff, less clutter in the home and more experiences.”

And while trips abroad might hold a certain appeal, Wilkinson said sticking close to home for those looking to pinch a few pennies also can yield memorable experiences.

“There are a lot of places off-the-beaten path throughout the U.S. that are absolutely worthwhile,” she said, counting her native Michigan’s Upper Peninsula among them.

But, Wilkinson said, it’s helping create memories for clients that makes the most of her career shift.

“I never expected to be doing this,” she said. “But it’s really special to be a part of that for people.”

Megan Gloss writes for the Telegraph Herald.