Life Is a Highway!
by Kevin Fritz
Meet the Dooleys, a local family of four that has left their traditional way of life behind for the open road and a world full of possibilities.
Parents Jill, 35, and Derek, 36, along with their young daughters Maddie and Rylyn, traded brick-and-mortar lodging last year to live full time in an RV – opting for new experiences and memories over set schedules and routines. They document their fun and relatable adventures, including the occasional bump in the road, on Instagram (search for Rolling with the Dooleys).
“We have wanted to travel for a long time,” says Jill, who met Derek when they were students at Lake Mary High School. “We always wanted to experience more than Central Florida.”
The closest the couple had come to traveling was when Derek went to college in Nashville, Tennessee, where they spent a couple of years. When Maddie, now six years old, was born, they moved back to Seminole County to be closer to family.
A few years went by, but their yearning for adventure remained. Derek suggested the couple buy a recreational vehicle and live on the road, traveling wherever they wished to point the headlights. Jill, however, was hesitant.
Roll With It
“I had never even been camping,” she says with a laugh, “but once Derek put that idea into my ears, I couldn’t stop thinking about it, and it began to happen very quickly. Within two months, we had sold our house in Sanford and bought an RV.”
A teacher at Woodlands Elementary at the time, Jill knew she had the ability to homeschool their daughters. And because Derek worked remotely in data analytics, the die was cast.
By June of 2025, the Dooleys were on the road, making life a daily adventure in the family’s 42-foot Jayco 5th wheel, weighing 28,000 pounds fully loaded. Pulling their new home was the family’s other new purchase, a Chevrolet Silverado 3500HD truck. In between their excursions, the Dooleys have a base at Jill’s parents’ home in Lake Mary, who have an RV hookup on their property.
The RV the Dooleys selected has many homey amenities, including a kitchen with an island, a living area, dining space for four, and two sleeping sections – a bedroom for Jill and Derek and a kids’ play area with a loft for bedtime.
“It’s a tiny home with modern conveniences,” says Jill. “And everybody still has their own space. That’s important.”
On the Road Again
By the beginning of 2026, the Dooleys had been roving for 15 weeks, remaining in Florida the whole time and visiting places that these Sunshine State natives never knew existed.
Some of the family’s favorite spots have been the spectacular Blowing Rocks Preserve on Jupiter Island and exploring Key West, while staying on Long Key for 10 days. Maddie and little sister Rylyn, who is four, are fully embracing their new lifestyle, including homeschooling with their mom. They love the outdoors. And no matter the destination, there is usually a pool at their disposal.
“I love going to new places and meeting new friends,” says Rylyn.
“I like going back and forth to different campgrounds,” adds Maddie. “There is so much stuff to do!”
In May, the Dooleys will make their first out-of-state trek, driving up the East Coast, with the end goal being Acadia National Park in Maine. In 2027, the family will venture out West.
“It has been an adventure and a learning curve,” says Derek. “But we’re learning as a family, and I love the fun we have had together.”
Adds Jill, “We have met families doing the same thing and we’ve also met new friends. We may be a family of four, but we are part of a big community.”