The Top Stops in Winter Park

Spend a day in Winter Park, from posh Park Avenue to the picturesque lakes.



Sidewalk cafes are plentiful in Winter Park

©Julie Fletcher/Visit Florida

Winter Park was a tourism destination in Central Florida long before Walt Disney World. Northerners flocked to this picturesque community surrounded by lakes and moss-draped oak trees for the mild climate, hence the name Winter Park. Today, the area still has that same charming allure of 100 years ago, with sidewalk cafes, quaint boutiques, amazing art museums and fun ways to get out on the water. Plan to spend a day—or two—along Park Avenue, in Hannibal Square, on the lakes and on the beautiful campus of Florida's oldest college, Rollins College.

Tips:

  1. Stop by 151 W. Lyman Ave. for free resources, maps and expert advice on exploring the area.
  2. Parking may look scarce on Park Avenue during peak times like lunch and dinner, but there is plenty of parking on the side streets.
  3. Central Park is a great place for a picnic while the children run around and expend energy.
  4. The SunRail train station is walking distance to shops and restaurants on Park Avenue.
  5. Winter Park is extremely walkable, so be sure to wear comfortable shoes for a fun day exploring.

 

ATTRACTIONS & ACTIVITIES

CHARLES HOSMER MORSE MUSEUM OF AMERICAN ART

Gaze in awe at the world’s most comprehensive collection of ornate stained glass windows and lamps, blown glass, pottery, jewelry and paintings by Louis Comfort Tiffany. The museum features the breathtaking Tiffany Chapel as well as a fabulous gift shop.

CORNELL FINE ARTS MUSEUM AT ROLLINS COLLEGE

Located on the picturesque lakefront campus of Rollins College, the free and open-to-the-public museum features an expansive collection of European and American paintings, sculpture and decorative arts, alongside student and visiting artist exhibitions.

PADDLEBOARD ORLANDO

Explore one of Orlando's hundreds of lakes by way of paddleboard or kayak. Choose from beginner lessons on the beautiful Lake Killarney or take a full-day excursion to Wekiva Springs.

WINTER PARK SCENIC BOAT TOUR

See why Winter Park is considered the "Venice of the South" by navigating its beautiful lakes and canals on this one-hour narrated tour. Gaze upon million-dollar-plus waterfront mansions while hearing the history of this quaint community.

SHOPPING

WINTER PARK'S PARK AVENUE

Take a stroll down charming Winter Park's iconic main street where you'll find upscale boutiques offering everything from fine jewelry and high fashion to rare antiques and funky gifts. With a perfect blend of retailers, such as Pottery Barn and Restoration Hardware, and independent  boutiques like Tuni, Synergy and Doggie Door, Park Avenue holds a little something for everyone. Check out the unique beauty and symbolism of Alex and Ani's American-made, eco-friendly jewelry—a must-have for today's mindful fashionistas. Have a craving for a bit of nostalgia? Tap into your inner child and head to Sassafras Sweet Shoppe where you can load up on blasts from the past like rock candy, Pop Rocks and Fun Dip.

TRADER JOE'S

This specialty grocery store chain is a fan-favorite for shoppers looking for unique and quality items at discount prices, like the three-buck chuck wines or the oh-so-good cookie butter. 

RESTAURANTS

COCINA 214

A fusion between a traditional Mexican kitchen and Dallas-style Tex Mex, the contemporary menu combines bold flavors with fresh, local ingredients to create truly unique dishes. Sample one of their 29 draft Mexican beers or a refreshing house margarita.

CASK & LARDER

Described as a "Southern Public House," this local favorite offers distinct seasonal dishes, locally sourced produce and provisions, craft beers micro-brewed on-site and fresh-shucked oysters from the oyster bar in a chic, rustic setting.

THE COOP

A sister restaurant to award-winning Chef John Rivers' local phenomenon 4 Rivers Smokehouse, this fast-casual country kitchen features gourmet comfort food classics made from scratch.

HAMILTON'S KITCHEN

Nestled in the boutique Alfond Inn hotel, this high-end culinary experience encapsulates traditional Southern cooking in a rustic, yet modern atmosphere.

Want more Winter Park? Read Part 2 here. 

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