Winter Park is just 15 minutes north of Orlando, but it feels light-years away. More upscale college town than suburb, the city of 30,000 got its name in the 1880s thanks to wealthy Northerners who flocked there for a warm-weather escape. Today, it offers the perfect palate cleanser for a theme park–packed holiday.
Things to See and Do
The Charles Hosmer Morse Museum of American Art has the world’s largest collection of Louis Comfort Tiffany works, and there’s much more to the artist than leaded stained-glass lamps. On display is everything from jewel-laden necklaces that make his dad’s Tiffany & Co. diamond rings look dull to a chapel interior with a marble altar, mosaic arches, and bejeweled chandelier. Continue your art tour with a stop at the Albin Polasek Museum and Sculpture Gardens to see the Czech American’s figurative bronze work, and then swing by Rollins College to see the new sculpture of the school’s most famous alum, Fred Rogers. Finally, take a Scenic Boat Tour along three lakes and two canals, where you can spot alligators and ogle Spanish Revival–style mansions.
Where to Eat and Drink
James and Julie Petrakis are considered Orlando restaurant royalty, and for good reason. Their first place, The Ravenous Pig, revolutionized the local food scene when they opened it in 2007.
The James Beard–nominated husband-and-wife team have debuted three more dining concepts since then, but the original gastropub remains a must-visit. Try the house-cured charcuterie, and be sure to add a couple of seasonal vegetable sides (grilled Broccolini with pimento cheese, perhaps?) to your pork belly main course. If you’re craving Italian instead, head to Prato, a see-and-be-seen spot on tony Park Avenue where chef Brandon McGlamery wows with handmade pastas and wood-fired Neapolitan-style pizzas.
Where to Shop
Boutiques are abundant here. Make your first stop Rifle Paper Co. for the local brand’s signature stationery and note cards, as well as floral pajamas, candles, and the cutest doggy bandannas you’ve ever seen. Next, pop into Piante Design for a Zen peek at artfully arranged terrariums and botanical creations. And at Tuni, a women’s clothing shop fashionably curated by a mother and daughter, a stylist will help you decide if you can pull off vegan leather shorts. (Answer: yes.)
Where to Sleep
The Alfond Inn is owned by Rollins College, and your stay will actually help fund a student’s education, as the net operating income of the hotel goes to the school’s scholarship fund. Another perk of that partnership? The property is home to The Alfond Collection of Contemporary Art, a bevy of stunning works from the Rollins Museum of Art’s permanent collection. And the rooftop pool is a work of art in itself; you’ll feel like you’re doing laps at a Spanish-Mediterranean villa, not in Central Florida.
From $332, thealfondinn.com