The Top Things to Do in Winter Park

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.


  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 extemely walkable, so be sure to wear comfortable shoes for a fun day exploring.


Winter Park's Park Avenue

Stroll along Park Avenue, the main street of charming Winter Park, where you’ll find upscale stores offering fine jewelry, antiques, books, shoes, cosmetics and gifts as well as the latest fashions.

Morse Museum of American Art

Featuring the world’s most comprehensive collection of work by Louis Comfort Tiffany, including glass windows and lamps, blown glass, pottery, jewelry, his 1893 chapel interior and art and architectural elements from his celebrated Long Island estate, Laurelton Hall.

Cornell Fine Arts Museum at Rollins College

Featuring a prestigious collection of European and American paintings, sculpture and decorative arts, alongside student and visiting artist exhibitions on the beautiful lakefront campus of Rollins College. Free admission. Open 10 am-7 pm Tu, 10 am-4 pm W-F, noon-5 pm Sa & Su.

Alex and Ani

Alex and Ani have made it their mission to share the benefits of positive energy through the unique beauty and symbolism of their jewelry, which are American made and eco-friendly.

Luma on Park

Creativity is on the menu with dishes such as sesame-crusted salmon and Crystal Valley chicken. The food is excellently served in an ultra-modern space with cutting-edge decor. D (nightly).

Cocina 214

The menu combines bold flavors with fresh, local ingredients to create contemporary Tex-Mex. Try the brisket tacos, chicken tamale or truffle and mushroom quesadillas and take a seat at the bar and enjoy one of its draft Mexican beers. L, D (daily), Br (Sa-Su).

Cask & Larder

This local favorite offers Southern-sourced seasonal dishes and craft beers at a new location in the Orlando International Airport. 


A picturesque setting on the lake with inviting Adirondack chairs and a dock. The dining room serves well-executed steaks, seafood and salads. L, D (daily).

The Ravenous Pig

This nationally renowned gastropub serves gourmet pub fare, raw bar delicacies and pasta. The menu changes regularly, with ingredients reflecting the season. A careful collection of micro-brewed beers are on tap in addition to an extensive wine list. L, D (daily), Br (Su).

The Coop

The fast-casual restaurant leads with southern hospitality featuring comfort food classics made from scratch daily. Signature dishes include "Southern Fried Chicken" and "Low Country Shrimp and Grits"and a wide selection of housemade desserts and seasonal pies.

Hamilton's Kitchen

This spot at the Alfond Inn welcomes friends and families to enjoy traditional Southern cooking in a rustic, yet modern atmosphere. B, L, D (daily), Br (Su). 

Paddleboard Orlando

Orlando is home to hundreds of lakes, and getting out on a paddleboard or kayak is the ideal way to explore. Choose from beginner lessons on the beautiful Lake Killarney or take a full-day excursion to Wekiva Springs. Open daily.  

Winter Park Scenic Boat Tour

Relax on this one-hour narrated tour through the lakes and canals of beautiful Winter Park. See waterfront homes while learning the history of this quaint community. Rides daily from 10 am to 4 pm, cash or checks only.

Alfond Inn

This beautiful boutique hotel has been recognized by Conde Nast and recently opened as a unique fund-raiser partner to Rollins College. The lobby is filled with contemporary art from notable artists, and Hamilton's Kitchen is a popular spot for lunch and dinner among visitors and locals.