The Rodeo Drive of the South

New-world sophistication meets old-world charm in scenic Winter Park, a picturesque city known for its tree-lined brick streets, high-end dining and upscale boutique shops. Originally founded as a winter resort in 1887 for wealthy northerners escaping the cold, Winter Park has developed a reputation as one of Central Florida’s swankiest historic destinations. For families, singles and couples, there are plenty of things to do in Winter Park.

Posh Park Avenue is a hotspot with trendy wine rooms, James Beard-nominated restaurants, adventurous gastro pubs, museums and chic art galleries. Indulge in an off-the-beaten path experience with a guided boat tour through the tranquil Winter Park chain of lakes. Breathtaking views of swaying palms, exquisite private homes and sprawling estates are just a few sights along the way.

Winter Park is also home to charming Rollins College, ranked the No.1 Most Beautiful College Campus by The Princeton Review, 2015-2016. Admire the lush landscaping, Spanish influenced architecture, and scenic lakefront paths on the grounds, and you’ll quickly see why.

We’ve compiled helpful insights from local experts:

A Year-Round Hotspot, Winter Park is Always in Season

Featured Winter Park Articles