This little Florida city might be your new favorite winter escape

Winter Park, Florida wasn’t just named for winter. It was built as a sunny escape from it.

True to its name, Winter Park was created in the 1880s as a planned community designed to draw affluent Northerners seeking a warm refuge from harsh winters. Today, this picture-perfect Orlando suburb, located just 30 to 45 minutes from the major theme parks, still fits that narrative for vacationers. While it can get a tad chilly — think light sweaters and jackets at night — the weather in winter is usually mild and pleasant.

THE VIBE: It’s a posh enclave of oak-shaded brick streets, a charming town clock, and bright flowering gardens where families love to play and couples walk hand in hand. The kind of neighborhood that feels straight out of the world Mr. Fred Rogers sang about in his famous show’s theme song, “A Beautiful Day in the Neighborhood.” Mr. Rogers actually went to college in Winter Park and spent his winters writing from a quiet home along the lake.

Scenic boat rides glide across the city’s chain of lakes, locals and visitors spill onto Park Avenue for shopping and brunching, and whole days disappear while you wander museums. It’s the perfect escape from theme-park chaos, but close enough if you want to jump in. Winter Park always has something going on, but a big draw in the winter is the Winter Park Sidewalk Art Festival, a premier art show in March. And Park Avenue is always decked out for the holidays.

DO: The Park Avenue District is the shopping epicenter of Winter Park, with a picturesque street lined with high-end boutiques and restaurants. Pop into clothing stores and specialty shops selling everything from olive oil, teas and chocolates.

But this is a smart town, and museums and art also reign supreme. If you love those stained-glass, nature-inspired lamps and leaded glass windows created by Louis Comfort Tiffany, The Charles Hosmer Morse Museum of American Art holds the artist’s most comprehensive collection. Soak up the glittering glass art, lamps, windows, jewelry and more from the Gilded Age. There’s also the Rollins Museum of Art, located on the Rollins College campus, that’s free for all.

One of the best things to do in Winter Park is the Winter Park Scenic Boat Tour, a $20 tour that’s been around since 1938. During the one-hour boat cruise, you’ll drift through tree canopied canals and the different lakes to peep at mansions and hear about the area’s history and notable residents.

Mr. Fred Rogers is a legendary name in these parts, and it’s worth taking the self-guided Mr. Rogers Neighborhood Walking Tour through Rollins College, where he attended school and met his wife. You can download the app for an audio tour, and you’ll see one of his famous sweaters, artwork, and learn about his life-long dedication to serving others.

At sunset, make your way to Kraft Azalea Garden, a peaceful public park that weaves along Lake Maitland. It’s magic at golden hour, with the sun’s rays radiating through the towering cypress trees draped in moss. It’s also a popular place for romantic dates and sunset wedding ceremonies.

Another botanical stunner is the 50-acre Harry P. Leu Gardens, which plays host to regular exhibitions and events that range from lakeside yoga to painting classes.

DINE: Park Avenue is where most of the popular Winter Park restaurants are located, everything from newcomer AVA Mediterraegean, Italian-centric Prato, to the always busy Briarpatch restaurant, which focuses on Florida produce (and there’s always a long line outside).

At the top of the street, you’ll find AJ Chocolate House, a European chocolatier with cases filled with premium artisanal chocolates, some crafted in whimsical shapes like lips or crowns. Expect the unusual, as many are filled with surprising flavors — the blue cheese flavor won me over — and liqueurs. The cabinet filled with decadent cakes like the Dubai chocolate cake will also tempt you to forget about your waistline and splurge for a slice or two. AJ’s is popular for Sunday brunch, and if you’re with the gals, order their tea tower for two, served with waffle bites to be dipped in chocolate, dessert shooters and chocolates of your choice.

Within driving distance from Park Avenue, Flutes Champagne Bar is a buzzy place to grab a glass or bottle of fancy bubbly, while mingling with the locals. They’ll even pair a flight of wines with a selection of AJ’s chocolates, or you can do a board of specialty cheeses.

STAY: Just minutes from the constant parade of people on Park Avenue — and intermingling with the area’s gorgeous residential homes — sits the boutique hotel The Alfond Inn. Like the artsy neighborhood where it’s planted, this refined spot feels like a living museum, filled with ever-evolving pieces from The Alfond Collection of Contemporary Art.

Step into the lobby and you’re immediately greeted by hulking oil paintings and standout works — around 130 pieces in all mediums sprinkled throughout the hotel. (Cool fact: The hotel is owned by nearby Rollins College, and its net income goes directly toward funding college scholarships.)

Guests can spend the day lounging at the rooftop pool or booking a spa treatment that includes access to the private spa pool. The spa features a sauna, steam room, and heated loungers that feel like heaven, and treatments for the face or body are worth the splurge. For breakfast or dinner, grab a table on the outdoor terrace at Hamilton’s Kitchen and dig into Southern comfort favorites like cornbread with whipped orange blossom honey butter or a cozy bowl of chicken and dumplings.

The rooms are perfection, and if you’re lucky enough to reserve one of the luxury suites, you’ll get a full kitchen, separate living and dining areas, and indulgences like a soaking tub. Wake up early and wander the surrounding neighborhood to admire all the beautiful homes.

Tip: If you love art, hotel guests can join 60-minute art tours on the first Wednesday of every month.

This story was originally published December 15, 2025 at 4:36 PM.