All at once uptight (no more burger joints!) and down-to-earth (wanna go get a burger?), Winter Park is the college town that isn't a college town. Park Avenue is prime for shopping and celeb spotting; Hannibal Square can host a hell of a pub crawl if you time it right – they stop serving alcohol at midnight.
One consequence of being landlocked: Orlandoans flock to water like anhinga birds. The landscaped patio at Shake Shack in Winter Park overlooks Lake Killarney, and is a sweet place to slurp a Fair Shake coffee treat and eat a drippy, delicious burger.
Shake Shack, 119 N. Orlando Ave., Winter Park, 321-203-5130, shakeshack.com
Beyond its sandy, stunning Spanish-colonial architecture, Knowles Memorial Chapel on the Rollins College campus houses stained-glass windows designed by Louis Comfort Tiffany. Take in a Bach Festival concert here for an unforgettable evening.
Knowles Memorial Chapel, 1000 Holt Ave., Winter Park, 407-646-2115, rollins.edu
You love soda, sure. But do you love marshmallow soda? How about sweet-corn pop? The walls of sweet shop Rocket Fizz on Park Avenue are lined with Technicolor treats, including plenty of inventively flavored carbonated beverages. Grab a chilled one and walk down the avenue to people-watch.
Rocket Fizz, 520 S. Park Ave., Winter Park, 407-645-3499, rocketfizz.com
From his early dream of opening a BBQ joint with no indoor seating and a line out the door, John Rivers' empire is now vast and varied. His 4 Rivers Smokehouse now has 13 locations, from Jacksonville to the newest spot in Coral Springs (including one at Orlando's City Hall), and he's moved into the fried-chicken arena with his down-home Southern spot, the Coop.
4 Rivers Smokehouse, multiple locations, 4rsmokehouse.com
The Coop, 610 W. Morse Blvd., Winter Park, 407-843-2667, asouthernaffair.com
Bikini-clad Rollins College students and families with kids in tow launch their paddleboards and boats, laze on the sand and swim off the jetty at Dinky Dock, just off Lake Virginia. Winter Park Scenic Boat tours pass through every so often, and wakeboarders show off their moves here, too.
Dinky Dock, 410 Ollie Ave., Winter Park, cityofwinterpark.org
Cheese, please. Toasted's menu of grilled cheeses teems with sandwiches both sweet and savory, but the Fig & Goat – havarti, goat cheese, fig spread, basil and honey – is both elegant and comforting.
Toasted, 1945 Aloma Ave., Winter Park, 407-960-3922, igettoasted.com