Willa and Andy Powless – Soaring Through Life with Grit, Grace, and Gulf Breezes

If you ask Willa Powless what makes Tierra Verde special, she doesn’t hesitate.
“It’s our island of paradise,” she says with a smile. Since 2002, Willa and her husband Andy have called this slice of sun-drenched serenity home. “Our backyard is the beautiful Gulf of America, and we are so blessed that we get to wake up to that every day.”  What more could you ask for?

Anchored in Love & Adventure
Andy is a small-town guy from Flora, Illinois, who had big Florida dreams. Willa was born on Columbus Air Force Base in Mississippi and raised in Tampa. They met, fell in love, and started their dental practice on Davis Island together. In their spare time they restored an old family sailboat together and Andy sailed it to Cuba. “There was no way I was doing that,” she laughs. “So I stayed behind in Naples with his family. Little did Willa know he was going to ask her to marry him in Cuba. But the magic wasn’t lost. On the return voyage, Andy proposed off the coast of Anna Maria Island at sunset. “That was the beginning of our boating passion,” Willa says. The couple married shortly after and moved from South Tampa to Tierra Verde, where they’ve been rooted for over two decades.
Their home, one of the original houses on the island, needed major renovations. “Everything was pink, white, and mint green—pure ‘80s!” Willa recalls. “We left three walls standing to keep the taxes down. We got in after the housing crash, bought materials at a discount, and took advantage of tax credits.”

A Close-Knit Family with Big Hearts
Married for 24 years and together for 30, Andy and Willa have three kids: Ava (22), a recent graduate from the University of Kentucky majoring in Fashion Merchandising and Communications; Johnny (19), studying at USF; and Jake (15), who attends St. Pete High and is actively involved in 100 Teens who care. Each has a heart for service and resilience to match—just like their parents.
Willa, a registered nurse, currently cares for her 92-year-old father in assisted living. She’s on leave from working at Andy’s dental practice, where the couple has weathered more storms than most.
“We had a devastating fire at the dental office,” Willa shares. “We lost $300K in renovations, then Andy had a bad ski accident right afterward.” With seven surgeries, he couldn’t work for six months.” But they didn’t let it break them. Instead, they rebuilt—working from borrowed spaces until they found a temporary office and eventually restored their own. “Our daughter Ava even changed schools to drive the boys to class so I could work,” Willa says. “She wrote her college essay on how our family doesn’t wallow. We just keep going.”
Fortunately, a new chapter is unfolding. Ava and Willa recently bought Canvas Fashion Gallery on 1535 4 St N. “That is our newest endeavor,” smiles Willa. 

Weekend Vibes & Sunset Rituals
Weekends in the Powless household are all about connection. Whether they’re hosting friends, doing yoga at home, enjoying sound bowl meditation, or watching the sun dip below the horizon at Fort De Soto or the Don CeSar, they make time for each other.
“We used to be on the boat every weekend at the sandbar or Shell Island,” Willa says. “It’s under repair right now, but we’ll get back out there soon.” Andy grew up boating, and their love of the water has become a family legacy.
When they’re not on the sea, they’re often in the sky. Andy is a pilot, and they keep a small plane at Albert Whitted Airport. “I’ve been flying with him for 30 years,” Willa shares. “Now I’m working on my pilot’s license, too.” They even unwind with aviation documentaries like Why Planes Crash—“so we know what not to do,” she laughs.
Their Jack Russell terrier, fittingly named Jack, rounds out their crew.

Giving Back, Lifting Up
Beyond the beach and family time, the Powlesses pour their hearts into the community. Willa is a committee member of 100 Women Who Care St. Petersburg, a philanthropic powerhouse that donates directly to local nonprofits. “That is my number one group,” she says proudly. “My best friend Christina Norstar started it, and I’ve been with it since the beginning.”
She’s also active in the new Tierra Verde Rotary—both she and Andy are corporate sponsors—and Andy recently joined 100 Good Guys, a giving circle of like-minded men supporting local causes. Together, the two groups are driving grassroots impact across the area.
The family also supports The Kind Mouse, a nonprofit feeding children in St. Pete. “Their office is right next to ours, and our kids volunteer to pack backpacks full of food,” Willa says.
Willa’s also involved in various human trafficking awareness efforts and hopes to one day launch a nonprofit tied to dentistry. “When bad things happen, you don’t really have a choice,” she says. “Our strength grows when we all work together.” 

Stronger Than Ever
Through the fires, literal and figurative, the Powless family has emerged even stronger. “When you have unity, you can get through anything,” Willa says. “We’ve lived that truth. And we don’t take a single day in paradise for granted.”
So the next time you see Willa and Andy out walking Jack, catching a sunset, or hanging out at the beach—say hello. They’re the kind of neighbors who remind us all what it means to live with heart, humor, and a whole lot of hope.