We’ve all been to Orlando, right? It’s one of the world’s biggest travel destinations because of all the theme parks, but there is actually so much more to it than that. My favorite place in the Orlando metropolitan area is Winter Park. It’s located about 40 minutes from where I live, so I spend a lot of time there and even go over just to shop at Trader Joe’s quite often.
Why do I love Winter Park? It’s a charming little town peppered with lakes and gorgeous homes of so many different styles. You’ll see a big Southern style house with a wraparound porch right next door to a Spanish casita and a London-style townhouse. On and around Park Avenue, there are tons of independent restaurants and boutiques. On certain evenings every month, you can watch a movie on the grass in the center of town and there’s the most amazing farmer’s market.
The next time you’re in the Orlando area on vacation, definitely check out Winter Park. Here are a few places to start your itinerary.
A darling brunch spot with a yellow-and-white striped awning situated right on the main street of Winter Park, this is the perfect place to go for Eggs Benedict or raspberry and brie stuffed French toast on a happy weekend day, or during the week for shorter wait times.
the glass knife
I love this new spot with its standout black, pink, and gold exterior and cute outdoor seating area. They’ve got a great selection of sandwiches and lots of desserts. This is a good spot for a counter service lunch that feels a little bit more luxe.
black bean deli
They have the absolute best tres leches cake I’ve ever tasted! It used to be in a small counter service spot with no tables, but now Black Bean Deli has a larger space just around the corner.
ethos vegan kitchen
I’ve been going to Ethos for years since well before they moved locations, but the food is just as good as ever! When you’re plant based, it’s so nice to go to a restaurant and be free to order literally anything off the menu. Check out Ethos for vegan versions of your favorite comfort food like lasagna, club sandwiches, and milkshakes.
This is one of my favorite spots in Winter Park because of the thought and quality that goes into each dish. It’s a beautifully decorated Spanish restaurant with great craft cocktails and a super knowledgeable staff. Even their salads are incredible, but I highly recommend you order a Moscow Mule and their cremoso de chocolate.
This chic spot feels like something you’d find in any big city and offers a nice menu of Italian dishes from margherita pizza and potato gnocchi to squid ink mafaldine and campagna.
Notably one of the best restaurants in the region, Hillstone has been featured in publications like Garden & Gun and Southern Living. It’s situated on one of Winter Park’s many lakes, with beautiful views and a menu that makes it a great choice for special occasions.
boca winter park
This cute little spot in the heart of Winter Park specializes in seasonal, sustainable, farm-to-table food. On the menu, you’ll find fresh from the garden dishes like strawberry gazpacho and heritage tomato caprese, as well as things like charcuterie boards, truffle fries, and classic cocktails.
I love this spot so much. It’s a coffee shop/cafe with a rustic feel on a tree-lined street with cute outdoor seating. The coffee and tea is really good, plus they’re eco-conscious with strawless lid cups.
the wine room
This is a really fun place for a girls night or a date if you’re in the Winter Park area. The gist is that you load up a card with whatever amount of money you’d like, then you can go around and fill your glass with all sorts of different wines priced by the ounce. This is where I first tried Meghan Markle’s favorite wine, Tignanello 😊
If you’re shopping along Park Avenue, definitely stop in for a coffee or tea at Barnie’s. It’s a cute little shop that sits on a courtyard where there’s a bookstore and an Origins shop, so it’s the perfect place for a midday break.
New General is somewhere that really reminds me of the places I’d frequent in Williamsburg when I lived in Brooklyn. The concept is a modern general store with sleek, minimalist interiors. You can grab a matcha latte or something off the seasonal menu, things like avocado toast, chia pudding, and granola bowls. Plus, they have a selection of home goods that you can shop while you sip.
One of my favorite shops in Winter Park is The Grove which carries lots of great, Palm Beach-inspired pieces. My favorite part, though, is that there’s a shop golden retriever who spends his days laying on the sidewalk outside or sniffing around customers inside.
This resale shop is across the street from Foxtail Coffee, so I recommend getting a chai latte and heading over. They carry brands like Free People, Supreme, Tory Burch, and more for great prices. Now, they’re not thrift store prices but the shop is curated with good quality pieces.
I love a good stop into Bluemercury, especially the one in Winter Park as it sits on a pretty corner on Park Avenue. Pop in for brands like La Mer, Dermalogica, African Botanics, and more.
This is a really cool plant shop that’s located inside of a huge, old fish factory. I swear, the first time I went in it still smelled like fish, although that’s not the case anymore! 😂 Not only are there rooms full of gorgeous plants, but they also have food/drinks and do events.
winter park farmer’s market
The WP Farmer’s Market is my favorite because it’s located by the train station on the cutest block, always filled with flowers and dogs and nice people. Not only are there produce and flower stands, but there are tons of vendors selling things like kombucha, lemonade, pineapple cocktails, and more.
see a movie at the enzian
This is one of the most charming theaters I’ve ever been to. It’s located on a shady corner in Winter Park with a beautiful outdoor seating area. The theater itself plays indie movies and documentaries while you sit on couches and eat a delicious meal or sip a glass of wine.
visit an art museum
There are actually quite a few art museums in Winter Park to visit, including The Morse Museum of Art featuring works by Louis Comfort Tiffany, the Cornell Fine Arts Museum, and the Orlando Museum of Art featuring exhibitions of both classical and modern art.
take a boutique fitness class
No matter what type of fitness you’re into, you can probably find a spot in Winter Park to do it. Take a spin class at CycleBar, try out Bar Method, Pure Barre, or barre3.