24 Hours in Winter Park (A Travel Guide)

By Brittni • Updated on 02/15/2024

When we were coming back from Harbour Island, Jeff and I stopped in Orlando for just over 24 hours. And I got a chance to show him around the city that I spent years and years of my life in.

Well…Sort of! We spent most of that 24 hours in Winter Park, which is technically it’s own city separate from Orlando.

BUT it’s basically the same thing. Considered part of the greater Orlando area in my book – much more quaint and interesting than Orlando though.

If you’ve never been, it’s definitely worth a quick visit, especially if you’re within driving distance. So, I put together a travel guide to make it easy…

Winter Park Travel Guide

Winter Park is about a 6.5 hour drive from Atlanta. So, it’s not exactly close by. BUT if you fly into Orlando (which is an hour and a half plane ride from ATL), it’s only about a 30 minute drive from the airport.

And if you’re planning to do any of the ‘big’ things in Orlando – Disney, Universal Studios, waterparks, etc, spending one day away in Winter Park is a nice change of pace.

Here are the coolest places to shop and eat in Winter Park…

That plant life

Coolest Places to Shop in Winter Park

New General

Far and away the coolest shop in Winter Park. They carry so many lines I love, from Yield Design and Wray to Herbivore and Minna.

Really well curated and the space is beautiful.

Rifle Paper Co

No Winter Park travel guide would be complete without a trip to Rifle.

You’re probably already familiar with the products that Rifle offers (paper goods and beyond).

And the store carries many of those things, along with some fun extras that I love, like Studio Carta ribbon (which you might remember I bought A LOT of while I was there – all the ribbon, please). And Rifle fabrics, which are a collab with Atlanta based company, Cotton + Steel (which has a studio in the same building as me – small world).

Porch Therapy (at East End Market)

So many plants, so little time.

That’s where all of the plant photos are from….and they have planters too. Plenty lovers unite.

Park Avenue

There’s a tree-lined street in Winter Park with little restaurants and shops and this is it.

It’s a good spot to take a walk and window shop – not tons of cool shops tbh, but worth a visit anyway.

Coolest Places to Eat in Winter Park

Buttermilk Bakery

This spot is really cute and they have AMAZING donuts and baked goods. And I also loved the avocado toast.

If you want something different / unique, try the hibiscus iced tea. Otherwise, their coffee menu is pretty good.

New General

Nope, I’m not having a stroke. I know this is the second time in this post I’m mentioning New General.

BUT aside from shopping, they also have great coffee, tea, and light bites too.

Did I mention, they serve food on some cute AF trays and have things like cold brew ice cream floats on the menu? I rest my case.

Swine & Sons

This spot is part quick eatery, part to-go joint. I didn’t get a chance to eat here, actually.

But it was recommended to me several times as a place to checkout. As far as I know, everyone LOVES this place. Next time, I’m totally going.

Lineage Coffee Roasting (at East End Market)

This is a cool little coffee spot inside East End Market. Everyone was super nice there. They even gave Jeff and I a couple of suggestions for more spots to check out while we were in town – like the next restaurant on the list…

Hunger St Tacos

This spot has a cool backstory and serves up tacos, tostadas, quesadillas, guac, and more.

Did I miss anything? Let me know if you’ve ever been to Winter Park and if I missed anything, be sure to remind me in the comments below.

And for more places to visit in the US, here are a few more of my fave places…
























10 comments | Click here to reply

[…] Winter Park, Florida (part of the greater Orlando, FL area): I lived in Orlando when I was a teenager and Winter Park is by far the best part of the greater Orlando area. We had a quick stay in Winter Park for the 12 trips series and I was able to put together a travel guide with some really great shops! It’s a pretty charming little place. […]

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Yay thank you! Going to Orlando in October actually. Added all these places to the list!



My sister is good friends with one of the co-owners at Lineage and brought back several bags of coffee beans after her last visit. Currently drinking Lineage coffee in rotation with our Atlanta coffees. 🙂


Fabulous place,this garden is beautiful
New post:http://thepinkpineappleblog.blogspot.com/2017/08/haute-couture-street-style-2.html

The pink pineapple

This looks like such a fun place! We’ll have to add it to our bucket list!


Paige Flamm

Aw, Jane. Hometowns are always a soft spot, huh? Definitely let me know how you like these spots next time you go back for a visit.


I grew up in Winter Park, FL and miss it so much! Thanks for sharing this guide – lots of new places to try and things to see when I go back to visit family.


It’s definitely a great place to spend 24 hours in, Michelle. 🙂 I’m not sure there would be a ton to do for more than say 48 hours in WP, BUT there’s plenty more to do in Orlando too, so it’s a good day trip.


This looks like such a cool place!

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