After growing up in North Carolina, I moved to St. Petersburg, Florida, at the age of 18 for college. That’s where I fell in love with my now-fiancée — and the surrounding Pinellas County.
We both adored Florida’s beaches, took regular weekend trips to Key West and Manasota Key, and thoroughly enjoyed life in the Tampa Bay area.
At times, I thought we might just stay there forever — but after graduation, the world felt wide open. So, we started “shopping around” the country for a new place to call home.
We tested Oregon, then returned to Florida — but neither was a perfect fit for us
My partner and I packed up my truck and started our adventure by road-tripping across the Western United States.
We camped in the Badlands, swam in the Yellowstone River, slept in a canyon in Idaho, and in 2020, landed in Portland, Oregon.
Portland was the epitome of cool — the kind of place where you could hike in the morning, grab a craft beer at night, and feel like you were living the hipster dream.
However, after six months, I found myself struggling with poor air quality from local wildfires and missing the familiarity of St. Pete.
So, we moved back to Florida, hoping to relive our college days with close friends and potentially settle down.
However, my fiancée and I struggled to put down roots.
Pinellas County and its housing market had undergone significant changes while we’d been away. Homes were selling for significantly more than they had been a few years ago, and many of those prices were far beyond our budget.
The rental market remained competitive as ever, too. We ended up renting a 400-square-foot ADU in the area for about $1,100 a month. At the time, it was the only place we found within our budget that had in-unit laundry and a decent location.
We made it work, and I even became friends with my landlord and his wife. However, heavy rain routinely flooded part of the unit, and after one particularly severe hurricane, the carpet was so soaked it had to be removed.
Between the worsening storms and rising house (and insurance) prices in the area, the idea of buying our first home here felt increasingly unrealistic.
We’d already been spooked by Hurricane Irma in 2017, and this felt like a small taste of the possible issues to come if we stayed.
Fortunately, by this point, I had a solid remote job, and we’d been building up our savings to put toward a down payment on a house.
Now, we had to figure out where to go next.
A small town in southern Wisconsin ended up being a great fit for our lifestyles and wallets
My fiancée suggested we move to southern Wisconsin, near where her family lived. Real estate was cheaper there, and we could stay with her parents while house-hunting.
I agreed, we moved, and we’re still happily here years later.
Our lives immediately felt different in a southern Wisconsin county with a population of about 100,000, in a town of less than 10,000.
After living in one of the most densely populated counties in Florida, home to nearly 1 million people, I was thrilled to find a quieter place to call home.
I’ve also fallen in love with the Wisconsin outdoors and all the adventures it has to offer. I’ve hiked Kettle Moraine State Forest, surfed on Lake Michigan, tested new fishing holes, and explored the lakes I’d only heard about before moving.
The locals seemed to welcome us instantly, and the community feels rich and full of life — new businesses always seem to be opening: a huge coffee shop, a speakeasy bar, and even a high-end restaurant.
Plus, the local “lake life” offered the same laid-back vibe we used to enjoy finding around Florida’s beaches.
Soon, we bought a four-bedroom house in the area, securing a mortgage that costs us less than $1,500 a month.
In less than a year, we’d gone from living in someone else’s tiny suite to having our very own four-bedroom home for a comparable monthly cost. We could hardly believe it.
Sure, winters can be a lot colder and tougher out in the Midwest, and we sometimes miss Florida, but I like the life we’ve built.
I always say if the hipsters in Portland or the beach bums in Florida knew about small-town Wisconsin, they’d move here in a heartbeat (or at least visit in the summers).
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