Winter Park – Central Florida’s Hidden Gem

There’s a bit more to Central Florida than Mickey ears and Harry Potter wands, and it’s located in Winter Park, only a few miles from Orlando’s downtown. Built as a winter escape, this enchanting enclave offers up culture, a hot foodie scene, eclectic shopping and a feel good vibe. Here are the can’t-miss-it spots.

Where to Go

Downtown Winter Park is truly authentic – there’s nothing contrived about its quaint and lively sidewalk culture. 

Make your first stop historic Park Avenue known for its brick-lined streets, lush foliage and European-style atmosphere. Yes, it’s sophisticated and on-trend. But it’s also got a nice touch of whimsy – dog bowls outside of shops and quaint side-alleys with trickling fountains filled with sunk pennies and coated with Mediterranean tiles. Explore chic boutiques, indie shops and fun eateries almost all with sidewalk seating. Flanked by a rose garden on one side and a performance stage on the other, Central Park anchors the downtown scene with a huge green lawn and vintage fountains. Find a nice shady spot to sip your iced coffee. Soak up the charm, then plot your next move.

Get Cultured

Long known for its cultural scene, explore the little and well known museums of Winter Park.

Vintage postcard of Palm Plaza Motel, Highway 7 and 92, Winter Park, Florida
Palm Plaza Motel, Highway 7 and 92, Winter Park, Florida. The Tichnor Brothers Collection, Boston Public Library, Print Department. a small town, the cultural offerings loom large. Drop into the Morse Museum of American Art and discover one of the largest collections of Tiffany glass works. Check out jewelry, lamps and brilliant windows. Be sure to explore the Tiffany Chapel exhibit, an intricate mosaic and glass chapel interior are museum highlights. Tucked inside the Rollins College campus, theCornell Museum of Art, is a less known museum that’s a wonder. This tiny jewel box features over 5,000 pieces of esteemed artwork, including works from Bierstadt, Matisse and Picasso. Catch another glimpse of memorable art at the Albin Polasek Museum & Sculpture Gardens. Located on three acres overlooking Lake Osceola, this museum lets you tour internationally-recognized artist Polasek’s home, galleries and sculpture gardens at your own pace.

Shop Here

Walkable brick streets loaded with charm offer up the best in indie shopping at Winter Park’s sometimes posh but rarely pretentious downtown. 

If you’re a book lover, hit up Writer’s Block Bookstore, a cozy independent bookstore that hosts a solid lineup of author events. The atmosphere is welcoming and the book shelves are well-stocked with a variety of titles and book club bestsellers. Wander over to The Grovefor trendy jewelry, unique gifts and cool boutique clothing. Don’t skip Hannibal Square, just a few blocks from Park Avenue. Pop into tugboat & the bird™ for a fairyland of adorable baby and kid apparel & toys. Next, walk a couple of blocks to the flagship Rifle Paper Co. store. Design and art lovers will adore everything from paper goods to Keds sneakers imprinted with artist Anna Bond’s popular illustration art. On Saturdays, you can mosey over to a side room housing discounted treasures in a variety of forms: stylized gift wrap, greeting cards, journals and tote bags.

Where to Eat

Foodie culture is thriving and innovative in this hip Central Florida hamlet, whether lakeside or downtown. 

Do yourself a favor – dine at Prato. This Italian eatery offers a sublime collection of entrees and appetizers created with the freshest ingredients. The creamy farro risotto with mascarpone, the truffle rigatoni, the coveted wood-fire pizzas – it’s all next level good. Even the humble meatball takes on revelatory status here.The Ravenous Pig is another perennial hit with locals. This award-winning New Southern restaurant is a real showoff. Biting into the truffle mac & cheese or the pan seared mahi mahi with grilled lemon and remoulade, you’ll understand why. Don’t leave town without a proper sendoff. Briar Patch still has one of the best breakfasts in town. Get there early and nab a sidewalk table to people watch while you polish off your breakfast burrito or stack of raspberry lemon cream pancakes. Even the restaurant chains have an extra dose of charm here. Hillstone, on the shores of Lake Killearney, offers a terrific lakeside scene complete with a fire pit and scattered Adirondack chairs next to handy side tables for cocktails and appetizers to be enjoyed al fresco.

Best Spots to Imbibe

Say cheers at stylish and ultra-cool bars and gastropubs many within walking distance of each other. 

Bar hounds will be tickled pink by Winter Park’s watering holes. Feeling hungry and thirsty? Skip over to Garp & Fuss, an imaginative gastropub where you can sip clever cocktails and local craft beer in the brick atrium with a glass-ceiling or the lounge area with comfy couches and chairs. Wherever you sit, you’ve got to nosh on the sumptuous charcuterie board – it’s a winner. Park Social, is the hang out for cocktail enthusiasts. Order the Ciro’s Old Fashioned or the I Wanna be Sedated. Everything’s better when you share though, so try one of their punch bowls such as the East 8 Hold Up, a concoction of Reyka Vodka, passionfruit, lime and pineapple. Saturday nights at Fiddler’s Green Irish Pub are filled with frosty pints of Smithwick and Guinness. Catch yourself singing along to Irish bands or guitar soloists – get festive, everyone’s Irish inside of Fiddler’s Green. For non-alcoholic fare, try Krungthep, an unassuming but wonderful tea bar. Menu items include the cult favorite bubble tea as well as a solid assortment of delicious teas and lunch items. Pair your beverage with one of their famous brick toast desserts. Order the Sleeping Beauty – Nutella, strawberries and whipped cream atop vanilla ice cream served on a delicate brioche toast for a sugary buzz.


Slumber at unique hotels right in the heart of Park Avenue, Winter Park’s main drag.

The Alfond Inn, a AAA Four Diamond-rated boutique hotel, is located just a few blocks from the hubbub of Park Avenue but still within walking distance. It’s modern décor, exemplary contemporary art and appealing restaurant, Hamilton’s Kitchen, make it a visitor and local go-to. Plus, you can bring your pooch, so no need to leave your best friend at home sulking. For a bit of old world elegance coupled with Southern charm, make a reservation at the Park Plaza Hotel right in the heart of downtown on Park Avenue. Built in 1922, this grand dame is home to 28 elegant rooms and only steps away from stellar dining and shopping along the avenue.


Embrace this tiny city’s chic culture and small town ambiance at one-of-a-kind events and experiences. 

Winter Park Scenic Boat Tour.
Winter Park Scenic Boat Tour. Photo credit:

Cruise on the nostalgic Winter Park Scenic Boat Tour, which has been in operation since 1938. Gawk at the posh homes and listen to fascinating facts & stories narrated by lively captains on this breezy ride through Winter Park’s lakes and canals. If you’re here the second weekend in March, the nationally-recognized Winter Park Sidewalk Art Festival deserves your attention. Discover talented artists from around the nation and globe showcasing their phenomenal art – watercolors & acrylic paintings, pottery, photography and sculpture all showcased along Park Avenue and Central Park. Plus, the street food is notoriously good. On Saturdays, head over to the Winter Park Farmers Market firmly rooted on New England Avenue staged at an old train depot. Instagram-worthy plants & flowers, hand-crafted goodies, artisanal honey, baked goodies and local food stands deliver the promise of delectable eats and amazing buys all in one spot. Finally, enjoy the free Enzian Theatre’sPopcorn Flicks in Central Parkon the second Thursday of every month surrounded by oak trees dangling with Spanish moss. Bring a blanket or lawn chair for a night at the movies underneath a starlit sky.