Explore Orlando

A Day Well Spent in Winter Park

Grab a coffee and a croissant and then follow our one-day itinerary to exploring Orlando, spotting Tiffany works at the Morse Museum, shopping along Park Avenue and exploring the city's restaurant scene.

Often referred to as "Little Europe," Winter Park gives meaning to the term “living well” and it offers visitors a peak into Florida’s gracious past. Cobblestone streets, pristine lakes and old, and often historic, homes are just part of what make Winter Park a must-see destination for visitors and a coveted neighborhood by locals. Perfectly blended into the tree-lined streets are some of the area’s top museums and galleries, as well as charming chapels with awe-inspiring stained-glass windows and buildings with character that could only exist in a tony town such as this one. While the town may be storied and established, it is anything but sleepy. I've built an itinerary to allow visitors the chance to truly experience the city’s character. Lose yourself in the luxury and relaxation of Winter Park.

8 am: Breakfast Amongst Tiffany

Winter Park is an upscale enclave located just minutes from downtown Orlando. Here you will find some of the city's best museums. A local favorite, the Charles Hosmer Morse Museum is the perfect place to start your morning (after you've grabbed a coffee and a croissant at Croissant Gourmet, of course). Home to the most comprehensive collection of works by Louis Comfort Tiffany, the Morse Museum is one of the most serene places to spend the morning. Prepare to be inspired by pieces like the Tiffany Chapel (shown in the World's Fair of 1893).

Start the morning off with a bit of culture at the Charles Hosmer Morse Museum (©The Charles Hosmer Morse Museum)
Charles Hosmer Morse Museum (©The Charles Hosmer Morse Museum)

1 pm: Shop Around  

A perfect day should consist of a little shopping and some time outdoors, right? Why not get the best of both worlds by shopping along Park Avenue? With a perfect blend of retailers, such as Pottery Barn and Alex and Ani and independent boutiques like Tuni, Synergy and Doggie Door, Park Avenue holds a little something for everyone.

6 pm: Dine Finely 

The beauty of Winter Park is that for every adorable shop, there's an equally amazing place to eat. Sure, you can venture off the Avenue after your day spent amidst art and fashion, but with options such as Prato, why would you? Serving up Itallian classics with a modern twist, and offering plenty of al-fresco dining space, Prato encourages good eating, great drinking and even better people-watching. Care to mingle or simply grab a drink? Grab a seat at the long bar and strike up a conversation with your neighbor.

Italian restaurant Prato in Winter Park
Grab a drink, a bite and a good view at Prato. (©Visit Orlando)