Road Trip: Winter Park, FL

PBI maps out must-see destinations around the scenic gem, located only 177 miles from Palm Beach

Although founded as a vacation destination in the 1800s, this idyllic city nestled north of Orlando feels quainter than its hustle-and-bustle neighbor. Winter Park has the vibe and walkability of a European village, complete with restaurants that celebrate Florida’s bounty through myriad culinary languages, as well as a wealth of art, museums, and natural beauty that’s next to none.


Part of Winter Park’s growth was due to the establishment of Rollins College. Today, The Alfond Inn is supporting Rollins students by directing its profits toward full scholarships for incoming liberal arts majors. While this mission is reason enough to book a room, The Alfond Inn also offers an unparalleled location and stylish surrounds. Guests can easily enjoy the city’s main street, Park Avenue, located two blocks away. They’re also invited to explore The Alfond Collection of Contemporary Art for Rollins College, which appears throughout the boutique hotel. Attend a happy hour art tour, held every first Wednesday, or peruse the pieces on your own and snap your favorite to share on social media.

Morse Museum

See + Do

In between all that eating, take advantage of the city’s landscape and museums. Learn

Winter Park Scenic Boat Tour; Photo by Mary Murray

the local history by setting sail with Winter Park Scenic Boat Tour. Afterward, head over to The Charles Hosmer Morse Museum of American Art, a treasure trove of all things Tiffany & Co. In addition to Tiffany jewelry, pottery, lamps, and more, it also houses objects from Louis Comfort Tiffany’s Long Island home, including a restored version of his Daffodil Terrace. The museum’s pièce de résistance, however, is the interior of the chapel Tiffany created for the 1893 Chicago World’s Fair.

Don’t Miss: On your way into Winter Park, stop at East End Market, a food hall situated just outside the city limits. Highlights include La Femme du Fromage, which specializes in innovative grilled cheeses, and Gideon’s Bakery, whose giant cookies have earned a cult following.


Begin at The Glass Knife, a quirky-meets-elegant eatery anchored by a collection of its namesake kitchen tool. The menu balances sweet and savory, including fresh doughnuts, pastries, and desserts. Continue on to Prato, which crafts Italian cuisine from state-sourced ingredients. The menu changes daily, but a reliable favorite is the meatball finished with cipollini agrodolce and polenta. No tour is complete without a meal—or more—at The Ravenous Pig. The seasonal menu is a study in familiar concepts elevated to the flavors of fine dining yet presented in a down-to-earth manner. Save room for the signature Pig Tails, a spin on churros.

Courtesy of The Ravenous Pig

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