7 cute places to visit in Historic Winter Garden, FL

It is a truth universally acknowledged that apartment hunting sucks.

When Zach and I found out about his new job, we also found out that he had to be in Orlando by the end of July. That was… three weeks away. In a hot real estate market, we knew snagging a decent apartment would be a grueling process, and since I didn’t have a job yet, we knew it’d be an expensive one, too.

We spent a weekend in Orlando touring what seemed like hundreds of complexes. We eventually found a place we really loved, but not before we were tired, frustrated, and super hungry.

To regain our strength during that weekend of stress, we decided to check out Historic Winter Garden. We wanted a quieter outing than one we would get at the theme parks in Orlando, and we also wanted to check out a few local sites in our new home.

Historic Winter Garden did not disappoint…

*Centennial Plaza in Historic Winter Garden.*

The Whole Enchilada

Our first stop downtown was a necessity: food. We’d skipped breakfast in our hurry to get started hunting, and by early afternoon we were starving. We passed the sign for The Whole Enchilada and immediately pulled the car over.

The restaurant features Tex-Mex cuisine. It’s one of those restaurants where you order at a bar and the employees bring you your food. I’ve always found restaurants like that to be a little nerve wracking, especially when I have no idea what’s on the menu. If you’re planning a visit to The Whole Enchilada, I recommend skimming the menu online so you aren’t rushed at the counter.

Zach and I both chose something at random, but I really enjoyed what I ordered. I got Skrimp Tacos, crispy shells filled with shrimp, cabbage, avocado, cheese, and cilantro sauce. The cilantro sauce alone was amazing—zesty but not overpowering. Zach got the Hasselhoff: chicken tacos. He enjoyed them but said he’d like to try something more adventurous next time (seriously, people, know that menu before you order).

*The Hasselhoff at The Whole Enchilada.*

Per an employee’s suggestion, we ate on the roof of the restaurant, where there was a bar and picnic table area set up. It was quite warm so I’d recommend not dining on top of a building in the dead of summer (in Central Florida, nonetheless), but it would be a cool place to eat at night or on an autumn day.

The view of downtown is pretty nice, too.

*View from The Whole Enchilada rooftop bar.*

Boutiques

After leaving The Whole Enchilada, Zach and I wandered down the streets of downtown, neither of us eager to return to the hunt. We stepped inside a few shops, and the Boutique on Plant was one of the cutest.

*The Boutique on Plant in Historic Winter Garden.*

The little store had everything from soft and floaty summer dresses to cool graphic T-shirts. I noticed a few interesting hats. One pink ball cap read in rainbow letters, “NAP QUEEN,” and, let’s be honest here, nothing would have fit me better in that moment.

Another shop I noticed but didn’t have time to browse was Adjectives Market. From what I gathered just by looking online and through the store windows, it’s Pier 1 Imports meets Anthropologie meets antique shop (it is, in fact, an antique shop). “Inspiring a home and style that you love” is Adjectives’ mission, and while I’m far from an interior design junkie, this place might convert me…

Writer’s Block Bookstore

No matter where I go, if there is a bookstore in the immediate area, I will invariably find it. Seriously, if I see any bookstore, be it local or mega, or even if I just see books on shelves, endorphins flood my body. Something happens when people see puppies and babies, right? They get super happy and excited? That’s what happens when I see books.

Anyway, Zach and I passed Writer’s Block Bookstore, so of course we popped inside for a minute. I love local bookstores, and I wish more existed. This one particularly has served the Orlando area since 2014, per its website, and it offers literary events, book clubs, community partnerships, and more.

*Hardcover books at Writer’s Block Bookstore in Historic Winter Garden.*

I decided not to browse too long, since Zach and I really needed to get back to our hunting, but once I get settled in the area I know I’ll be returning for a few titles. As a reader, a writer, and a lover of words in general, I can confidently say Writer’s Block Bookstore is one of the best things about my new home.

Coffee

Before getting back into the thick of things, we had to snag some caffeine. Luckily, Historic Winter Garden had a few options for us. I’m very finicky about coffee, and I usually prefer to make my own or hit up the nearest Starbucks, but every now and then I enjoy seeing what other cafés have available.

Axum Coffee did not disappoint. It had cute summer menu offerings, and the Cold Brew Lemonade was an interesting—but delicious—drink to help continue my day. I can’t wait to return and try The Malibu—cold brew and cream mixed with coconut and rum extract, topped with whipped cream and a colorful umbrella. Talk about a summer drink!

*Axum Coffee in Historic Winter Garden.*

And if you’ve got a sweet tooth (like Zach) you might want to check out Way Chocolate & Coffee. Way’s menu of not just coffee items but of chocolate dipped everything is darn near irresistible. I already know I’ll go back for candy treats, but I’ll also check out the various pastries and crepes the café serves.

*Way Chocolate & Coffee in Historic Winter Garden.*

Garden Theatre

Finally, it was time for Zach and I to hit the road. But we couldn’t get back to the car without passing the front of the beautiful Garden Theatre.

I did some research later and discovered the theater was originally built to show films, but now it puts on plays and musicals, and it shows concerts and “interactive movies.” The theater also hosts private events and summer camps for kids—and as an alumna of such a camp, I adore any organization that helps children discover their passions.

While there was no time that weekend for plays or musicals, I made a mental note to return for a performance soon and support this institution of local art. Big, the musical, will be performed later this year, and that alone is a can’t-miss show.

*Garden Theatre in Historic Winter Garden.*

If you’re visiting Orlando, I highly recommend stopping by Historic Winter Garden as part of your trip. It’s a beautiful location, with amazing food and shops, and you’ll enjoy supporting local businesses while on vacation. Don’t miss out on such great experiences!

Until next time, Dreamers!