True to its name , Winter Park was chartered in 1887 as a winter resort for wealthy – and cold – Northerners. It evolved into a suburb of metropolitan Orlando, but still retains the charm and character of a wealthy, small town, with excellent shops, bars, and restaurants, and a sprinkling of interesting museums. The areas of Maitland and Eatonville, to the north and east, are more residential, but also have some worthwhile attractions, which make a pleasant change from south Orlando’s mass-market theme parks.
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Morning
Begin with a hearty breakfast at the Briarpatch Restaurant . You’ll probably have to wait a bit, especially on weekends, so grab a newspaper. Then take time to wander the north end of Park Avenue , where a multitude of charming oneoff boutiques cater to up-scale shopping tastes. At Cole Avenue pop in to the Charles Hosmer Morse Museum of American Art ; its outstanding collection of Tiffany glass is a must-see. Follow this with a relaxing trip on the Winter Park Scenic Boat Tour , which departs from a dock on Morse Street, just a 15-minute walk away. On your return, lunch options are plentiful, but if the weather is good, grab one of the sidewalk tables at the R Bistro (see R Bistro of Winter Park) for some good food and serious people-watching.
Afternoon
After lunch, continue south on Park Avenue to Rollins College, home of the excellent Cornell Fine Arts Museum and spend the rest of the afternoon enjoying this small but excellent collection.
Evening
Then, it’s a ten-minute car ride north to Maitland’s Enzian Theater where you can settle in to enjoy the latest in US and foreign independent films with a bottle of wine and a cheese plate. End the day at the bustling Brio Tuscan Grille just a few minutes south by car, savoring a pink cosmopolitan or a gorgonzola-encrusted steak.
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Sculptor Albin Polasek moved here to retire, but in fact he kept producing his figurative works until his death in 1965. Now listed on the National Register of Historic Places, the museum and its sculpture gardens contain works spanning Polasek’s entire career.
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An Irish bar in a hotel usually inspires yawns, but the authentic An Tobar gets thumbs up. The beer selection could be better, but the Guinness and Bass suit the lowkey crowd.
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Think of this place as a halfway house for some of the most impressive examples of Florida’s birdlife. It was cre-ated by the Florida Audubon Society to rescue, rehabilitate, and release wounded raptors (birds of prey). Those that wouldn’t survive being released into the wild are kept here, living a pampered existence in a lovely lakeside location, while helping to educate visitors about wildlife issues and conservation. Guests aren’t allowed to observe the rehabilitation process, but permanent residents on view usually include vultures, bald eagles, screech owls, hawks, ospreys, and more.
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A bakery that doubles as a bar by night. The bakery is open six days (not Sundays) to 5pm, and the bar opens at 6pm Thursday to Saturday.
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The bar at this eaterie is often packed with an upscale crowd more interested in the score with each other than that of the sports matches on TV. Live jazz-funk groups play out back.
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Winter Park’s homey breakfast landmark is known for big omelets and fresh fruit platters, but the creative, healthy American menu will make you consider returning for lunch.
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The trendy grill at Brio is wildly popular, but a lot of people come just to hang out at the bar here. Cocktails flow fast and furious for a crowd of well-heeled locals.
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This local favorite has a huge dining room that buzzes with chatter and the sizzle of grilling in the open kitchen.
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Smoked meat is the name of the game at this family joint. The sauces to put on range from mild to killer hot.
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Restaurant price categories
For a three-course meal for one, a glass of house wine, and all unavoidable extra charges including tax.
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