Winter Park, Florida 2024

It’s easy to forget that you are in Central Florida while visiting Winter Park. The central downtown is lined with live oaks covered with Spanish moss and felt more like a small coastal South Carolina town than a suburb of Orlando.

Our goals for a girls’ weekend/college roommates’ annual reunion were easily met, including a little bit of nature and a museum visit, but mostly cocktails and good food. We rented an AirBNB, learning later from a local that the city of Winter Park has a lot of restrictions so they may be hard to find. Our other options were a small boutique hotel in Winter Park or staying just outside town in another part of Orlando.

scenic boat ride

One of the most popular attractions in Winter Park is the hour-long scenic boat tour of Lake Osceola. Tickets are sold first-come first serve from a kiosk. A series of small canals connects different sections of the lake. Our tour guide covered the history of the mansions that line the shores. We saw anhingas, also known as snakebirds, fishing on the lake and learned about the native plants of central Florida. Somehow, alligators had been removed from the lake so it could be more safely used for recreation.

Shopping & Dining

Winter Park is known for its dining scene, with multiple Michelin Star awarded restaurants. We were on a more laid-back last-minute reservation type vacation, so we opted for less fine, but also enjoyable, dining options. We checked off cuisine from around the world with Agave Azal (Mexican), The Bridge (Mediterranean), and Panullos (Italian) all within the downtown. We found the perfect brunch at Barnie’s Coffee & Tea, with outdoor seating in a courtyard that was hidden from the main street.

Upscale shops and small independent stores fill the street front along Park Avenue. Small shopping centers are also tucked back into courtyards and interior hallways and one of the more unique areas was filled with pools of koi fish.

We took a few excursions out of the downtown Winter Park area. The East End Market’s first floor is filled with kiosks and small local shops and restaurants. An elevator to the second floor leads to Neighbors, a bar and kitschy items retailer.

I knew of Gideon’s Bakehouse because I had seen long lines of Disney Springs patrons waiting in queues in the sweltering heat to get cookies. The indoor kiosk in East End Market also had a popular following, but we were able to secure our cookies (there was a strict 7-cookie per person limit) in far less time. We also grabbed vegan snacks from the Winter Park Biscuit Company and ate at picnic tables just outside the market.

Museums

The Charles Hosmer Morse Museum of American Art, Winter Park, Florida, 2023

There are a number of small art museums in Winter Park. The Charles Hosmer Morse Museum of American Art is home to the Louis Comfort Tiffany collection of glass art.

We watched two introductory videos that told the story of how and why the chapel and the rest of the art and architectural elements from Laurelton Hall, Tiffany’s Long Island estate, came together in Winter Park, Florida.

The museum displays The Tiffany Chapel reconstructed in the style of its original display at the 1893 World’s Columbian Exposition in Chicago.