At 21 years old, Alexa Wheeler was already working the real estate scene in Gainesville after graduating from the University of Florida. After some time in north Florida, it was back to South Miami with her husband, to own and operate a gas station during the very beginnings of self service. During those years, the couple purchased their second home in the Keys, and eventually, made the move south. After arriving and working three years in the vacation rentals industry, Wheeler decided to start Freewheeler Vacation Rentals in 1987. Five years later she opened Freewheeler Realty.

Wheeler has a little more free time now to vacation herself. She spends that time riding around on her Harley Wide Glide and flying around in her Cessna. Much like she did as a kid, she travels the country extensively. She’s been to the Bahamas, St. Thomas, all over Florida, North Carolina, Texas, Colorado, and is considering completing her “dream trip” sometime soon.


What’s the biggest difference in the vacation rental business over 30 years? Taking a call and writing it in the ledger book. We use to have index cards. It was amazing the time involved for that sort of thing. The automation of today’s industry is incredible. Everything is online. That and the governmental regulations.


What’s the most rewarding apart of helping someone find a home to stay in? Having visitors turn to me and say, “That’s the best vacation I’ve ever had, and I’ll be back next year.”


How does the vacation rental industry compete with trending companies like Airbnb? We work with those vacation booking platforms. Our new reservation system is integrated with those sites like VRBO, HomeAway, Airbnb, and Trip Advisor. It’s helped us.


Had you not gone into real estate, what could you see yourself doing? I would have stayed in the gasoline business. Before I looked into the real estate business I thought about buying a gas station down here. I looked at two places in the Upper Keys, and had that come to fruition I would have probably stayed doing that.


You and your husband met at the tender age of 15, and have been together ever since. Do you remember your first date?

We met water skiing. He went with a bunch of guys, and I went with a bunch of girls. We met one Memorial Day weekend. Our first date he picked me up and we went to Jimmy’s Hurricane in Coral Gables. In the backseat of his friend’s Volkswagen bug, the radio broadcast its nightly “kissing tone” and we had our first kiss.


Speaking of story book endings, you also are an avid reader. What’s your favorite book? I read at least one book when I’m away flying. I can’t say I have a specific type. I like the Vince Flynn government James-Bond type of books. Every once in a while I get a free book on the Amazon Kindle. I also read two or three articles out of my flying magazines in the morning, and the afternoon I’ll pick up my book.


Flying your own plane must be a hoot. Where’s your “dream trip” take you and your Cessna? From Florida to the west coast would be my dream trip. I think she can make it in three days. I just want to fly over so I can see the Pacific Ocean, then come back.


Have a nickname for the plane? Hawk, because it’s a Hawk XP. I have an Indian insignia of a hawk hanging from the sun visor, along with the set of wings my first instructor gave me.


If you could have lunch with any historical figure, who would it be, and what would you ask them? Amelia Earhart. And I would want to ask her, ‘What the heck happened?’


Describe the perfect day spent outdoors. I’d get up early, do a little yard work. Then I’d get out on the boat, and snorkel around, maybe look for lobster. Then I’d ride over and float out in the bay by Founders Park in a noodle.


Being outdoorsy, you must have some survival skills. That being said – you’re offered ten million dollars to survive in the wilderness for a month. You’re allowed one friend, one tool, and one type of food to eat for the duration of the time. Who and what do you bring? I’d bring my husband because, he’s a logical thinker. He was also in the Navy. A Swiss Army knife, but a big one, with lots of tools in it. Basically a shovel. And beef jerky, because it’s nutritious, it’ll last, and I like it.

Keeping active is something you say you’ve always done. How would encourage someone to do the same? I would tell them to surround themselves with people who are active the same way. Surround yourself with young people and positive people with the same mentality. And try to do something new every year.

Alexa Wheeler knows a thing or two about Keys vacations – and vacationing in general. GABRIEL SANCHEZ/ Keys Weekly


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