IT Manager
Roadtrips, Taxes, and Bougie Brunches
My go to friend for
Winter Park, Florida
2,858 miles
distance from bay area
How did we meet?

Alex and I met at work in 2016. He's the kind of guy that you just feel like he's lived a hundred different lives because you could pull a random topic out of a hat and he has an anecdote about it or has a good friend who is an expert on the topic. He's charming and enthusiastic and can get you motivated to start basically any project. He's also a badass baker.

We became friends after we went climbing for the first time after work. During that time I was trying to conquer my fear of heights and Alex, being the motivator that he is, convinced me to go with him despite the fact that I wasn't feeling ready. I cried as soon as I was 5 feet off the ground.

Despite a dramatic start, he decided to keep inviting me to hang out. We live a few blocks from each other and we started walking home from work and getting brunch together. We've talked about basically everything and if you need someone to praise the wonders of Florida, he's your guy. We have taken trips LA, Yosemite, Marin County and with this project I'm finally looking forward to Florida being exactly what he's been advertising because he sure has been hyping this trip up for almost three years.

welcome to

Winter Park, FLORIDA

population: 30,879
settled in 1882
surburbia but also palm trees

Winter Park is a suburb north of Orlando, right in the center of Florida. I think Alex was originally born in the adjacent suburb but Winter Park is his chosen hometown because the lakes there are "superior". Nothing personal, Maitland.

As many other areas of the country, Winter Park experienced most of its growth during the post-war boom of suburbia. The houses, now largely renovated, were once a string of mid-century modern designs placed in luscious yet perfectly manicured plots within a few minute drive from beaches, lakes, theme parks and all kinds of coastline resort entertainment.


Why is your hometown called Winter Park?

“Basically people in the early 1900s would travel down the coast to escape the harsh New England weather and they found this spot. Pretty much a resort from the beginning.”

Water activities are the backbone of Floridian life. Just in Winter Park there are one five lakes; so we did the math: When in Winter Park you are probably no more than a mile from a lake in any direction. So what do you do with that many lakes? Activities include tubing, fishing, and boating. Alex's dad has a boat and he's taken it on multiple adventures. "I've seen Carrot Top's lake side house from the boat, and I will take you to see it" he promised. Can't say no to that.

Suburban looks in Winter Park, much like the rest of the country mean multiple cul-de-sacs, parks, racket clubs and a golf course. The neighbors know each other and their kids go to soccer practice together. Alex's former grade school and middle school are so close, he says, that he could hear the school bell ring in the morning.

A key difference is that there just aren't too many suburban kids that get to live so close to the happiest place on earth. "It's a 30 minute drive from my house, with traffic." The impact of Disneyworld in the area is huge, with a large portion of the residents being employees of the company. Alex has been to the 4 different parks inside the compound dozens of times throughout his life and knows all the ins and outs but he's still thrilled to show me around. I'll make sure to say hi to Mickey.


What do you miss the most about it?

“The block parties that'd be thrown during the year. My block was the Christmas party block with fake snow and everything"


March 14-18, 2019

Winter Park Sidewalk Art Festival
Take the boat out for a ride
Go to Disneyworld (yay!)
Visit Florida Southern College
Ride down the St. John's River

see instagram updates from the road ✌🏼