Winter Park: Orlando

An upscale neighborhood a few miles to Orlando's north, Winter Park is a suburban oasis of brick paved streets, meticulously manicured lawns, and an artful and audacious array of modern and classic Mediterranean style residential architecture. Very few cookie cutter subdivisions exist with builders opting instead to redesign and update existing homes with million dollar facelifts both inside and out. A drive through Winter Park's residential streets is a highly pleasurable way to spend a few hours.

Winter Park is probably best known for the string of posh eateries and chic boutiques that comprise its downtown area, particularly Park Avenue and Hannibal Square. Downtown draws a crowd of Friday night happy hour drinkers, Saturday morning farmer's market snackers, and Sunday morning brunchers, all of which never hesitate to sport their Jimmy Choo handbags and Prada sunglasses. This is a well-healed crowd of hipsters without attitude. The area is beloved by families and couples alike who appreciate the bevy of festivals and free outdoor movies that take place in Park Avenue's Central Park throughout the month. Tours of Winter Park's chain of lakes, visits to its museums, and hours spent sipping and noshing on Park Ave are 'must do' activities. Be sure to take a stroll through Rollins College, the oldest university in the state.
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