Exploring Winter Park, Florida


Winter Park, FL

Whether you are a tourist or a local, if you are looking to experience elegant “Old Florida” charm, look no further than Winter Park, Florida, a city just north of downtown Orlando. Winter Park is home to Rollins College, wonderful museums, theater, festivals, a farmer’s market, beautiful lakes and parks, great shopping, and restaurants ranging from casual to fine dining. Winter Park, chartered in 1887, was originally a winter resort for wealthy Northerners. It would be easy for a family to spend a day in Winter Park and just scratch the surface of all there is to see and do. Here are some of my family’s favorites.


Winter Park really does boast of an amazing collection of museums. Our personal favorite is The Charles Hosmer Morse Museum of American Art on Park Avenue. The Morse Museum houses the world’s most comprehensive collection of the works of Louis Comfort Tiffany, including an entire chapel interior designed by the artist. The Albin Polasek Museum & Sculpture Gardens focuses primarily on American representational sculpture with over 200 works of Albin Polasek.

The Cornell Fine Arts Museum, located on the campus of Rollins College, is described as “one of the nation’s most innovated college art museums,” housing both permanent and traveling collections. Crealde, more than a museum, describes itself as a community based arts organization. In addition to offering classes, it houses three galleries and a sculpture garden on two campuses in Winter Park (the main campus off Aloma Avenue and the Hannibal Square Heritage Center).

Park Avenue

Park Avenue offers shopping, dining, and fabulous people watching. Shopping includes art galleries, one-of-a-kind boutiques, and higher end retail chains. I can’t even begin to select a favorite dining spot to recommend. You can find a range from casual to fancy, many with outdoor seating. One “must visit” for our family is Kilwins for ice cream in homemade waffle cones. There is a large park on one side of the street where festivals (like the Winter Park Art Festival) are held throughout the year. The park is a great place to let the kids run around and burn off energy. It’s also a great spot for snapping some candid kid photos.

Winter Park Scenic Boat Tour   

This is a “must do” on my list of Winter Park activities. The guided tours on an 18-passenger pontoon boat are offered every hour and take you on a tour of the Winter Park chain of lakes. The boats navigate through narrow canals offering views of gorgeous old homes tucked away on these lakes in addition to beautiful natural scenery.


Rollins College

Founded in 1885, Rollins College is the oldest college in Florida. The campus is tucked away on the shore of Lake Virginia. The brick-lined streets, Spanish-Mediterranean architecture, and old trees and plans along the lake make for a great background for photographs. Rollins is home to the Annie Russell Theater where you can catch a great show, and the beautiful Knowles Memorial Chapel.


You have to be lucky to find a parking spot on Park Avenue, but there are several free open parking lots just off Park Avenue. Enjoy exploring Winter Park!


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