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Tiffany glass, brick streets and boats gliding through canals shaded by cypress give Winter Park a character unlike the theme-park sprawl around it. The city of about 30,000 lies just north of Orlando and grew in the 1880s as a winter resort for wealthy Northerners, who built homes along its chain of lakes.
Rollins College, founded in 1885, still shapes the town with its Mediterranean-style campus, the Knowles Memorial Chapel and the Cornell Fine Arts Museum on Lake Virginia. Along Park Avenue, boutiques and sidewalk cafes face the oak-shaded Central Park, while the historically Black neighborhood of Hannibal Square has its own heritage center and restaurants.
Art is everywhere: the Charles Hosmer Morse Museum holds the largest collection of Louis Comfort Tiffany works, and the Albin Polasek Museum shows a sculptor's lakeside home. Downtown Orlando is 15 minutes away, and the theme parks under an hour.
Home to the world's most comprehensive collection of works by Louis Comfort Tiffany, including leaded windows, lamps, jewelry and the reconstructed chapel interior he designed for the 1893 Chicago world's fair. Allow at least two hours and check for seasonal free evenings.
The former home and studio of Czech-American sculptor Albin Polasek on the shore of Lake Osceola, with galleries of his work and gardens dotted with bronze and stone figures. The historic Capen House was moved onto the grounds. Guided tours of the residence run several times a day.
Rollins College's art museum on the shore of Lake Virginia, with rotating exhibitions drawn from a collection of thousands of works spanning old masters to contemporary art. Admission is free. Pair a visit with a stroll through the Mediterranean-style Rollins campus next door.
A 1933 Andalusian-style farmhouse designed by architect James Gamble Rogers II that was rescued and moved across the street in 2001 to save it from demolition. Today it hosts free tours, concerts and weddings beside the golf course. Check the schedule for Sunday open house hours.
A one-hour pontoon ride operating since 1938 that loops through Lakes Osceola, Virginia and Maitland via narrow, overhanging canals. Guides point out historic mansions, Rollins College and wildlife. Boats leave from the dock at the east end of Morse Boulevard; arrive early on weekends.
A natural garden with boardwalks through wetlands, a creek, native plant areas, a butterfly garden and an amphitheater, set within the city limits. Volunteers run plant sales and nature programs. Free to visit; mosquito repellent helps in summer, and morning walks are coolest.
A Spanish Mission-style chapel at Rollins College completed in 1932 to designs by Ralph Adams Cram, with a carved stone entrance, painted wooden ceiling and stained glass. It hosts services, concerts and weddings. When open, visitors may step inside quietly between events.
A Mediterranean Revival theater on the Rollins College campus that opened in 1932, named for the stage actress Annie Russell who taught at the college. Student and faculty productions run through the academic year. Look up the season schedule and book seats for evening performances.
Winter Park's main street is lined with independent boutiques, galleries, wine bars and sidewalk restaurants facing Central Park. The brick-paved side streets and courtyards hide more shops. Free two-hour parking is available on side streets and in the garage near the SunRail station.
The green heart of downtown along Park Avenue, with huge live oaks, a rose garden, fountains and benches where trains rumble past the SunRail station. It hosts concerts, art festivals and holiday lights. Bring a picnic from a Park Avenue bakery and enjoy the shade on a warm afternoon.
A small lakeside park on Lake Maitland shaded by enormous cypress trees and planted with azaleas that bloom from late winter into spring. A classical exedra monument frames the view across the water, making it a popular spot for sunset photos and quiet picnics. Parking is limited.
A Saturday morning market held in and around a historic railroad freight depot a block from Park Avenue, with local produce, baked goods, plants, honey and prepared foods. It is a local ritual, so arrive early for the best selection and easier parking, then walk to the shops after.
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