On our way back from Harbour Island, Jeff and I had a little over 24 hours to stop in Orlando. Instead of spending that time in the busy theme-park areas, I took him to Winter Park, the charming small city just north of Orlando where I grew up spending so much time.
Technically Winter Park is its own municipality, but to me it’s part of greater Orlando — only much more quaint, walkable, and full of interesting shops and local restaurants. If you’re in the area or driving distance from Orlando, it’s absolutely worth a day trip. To make planning simple, here’s a focused guide to the best places to shop and eat in Winter Park during a short visit.
Winter Park Travel Guide
Winter Park is about a 6.5-hour drive from Atlanta. If you’re flying, Orlando International Airport is only about 30 minutes away by car, and that makes Winter Park an easy addition to an Orlando trip.
If you plan to do the major Orlando attractions such as Disney or Universal, spending a day in Winter Park is a pleasant, low-key contrast: tree-lined streets, independent shops, and relaxed dining that feels far removed from the theme-park bustle.
Below are my top picks for shopping and dining in Winter Park, all easy to fit into a single day.
Best Places to Shop in Winter Park
New General
New General is the stand-out shop in Winter Park. The curation is on point: home goods, stationery, beauty lines, and designer collaborations I love. The store’s aesthetic and product mix make it a must-visit for gift hunting and browsing a beautifully designed retail space.
Rifle Paper Co.
No Winter Park shopping list is complete without Rifle Paper Co. The store carries the brand’s signature stationery and paper goods plus extras like fabrics and curated ribbons. If you’re into stylish paper goods, this location is a fun stop.
Porch Therapy (at East End Market)
Plant lovers will adore Porch Therapy. It’s packed with greenery and planters and a great place to stroll if you want houseplants or pretty pots—many of the plant photos in this post are from here.
Park Avenue
Park Avenue is the tree-lined street at the heart of Winter Park. Lined with restaurants, boutiques, and galleries, it’s ideal for a leisurely walk, window shopping, and soaking up local atmosphere.
Best Places to Eat in Winter Park
Buttermilk Bakery
Cute, cozy, and full of delicious baked goods. Their donuts are outstanding and the avocado toast is a favorite. Try the hibiscus iced tea for something unique, and their coffee selection is solid if you need a caffeine boost.
New General (yes, again)
New General doubles as a great light-eating spot. In addition to shopping, they serve coffee, tea, and small bites on charming trays. They even offer playful menu items, like cold-brew ice cream floats—perfect for a casual snack or light lunch.
Swine & Sons
This place comes highly recommended by locals. It’s a mix of quick-serve and to-go fare that people seem to love. I didn’t make it there on this trip, but it’s on my list for next time.
Lineage Coffee Roasting (East End Market)
A friendly, relaxed coffee spot inside East End Market. The staff were welcoming and gave us local tips for other places to try—definitely a good spot to refuel while exploring the market.
Hunger Street Tacos
Hunger Street serves tacos, tostadas, quesadillas, guacamole, and more, all with a strong backstory and creative flavor combinations. A great choice if you want casual, flavorful Mexican street-food-style dishes.
Did I miss anything? If you’ve been to Winter Park and have other favorites, I’d love to hear them—leave a note in the comments if there’s a spot I should add next time.
And if you enjoy exploring U.S. towns and cities, here are a few other favorite guides and trips to check out for inspiration on where to go next:
- Places in Richmond that you don’t want to miss.
- My picks for the best coffee in Atlanta (I lived there for five years).
- A Charleston travel guide with favorites for food and shopping.
- One of my favorite road trips: Atlanta to Asheville.