New York to Orlando = 2 1/2 hours
You’ve no doubt seen $200 tickets to Orlando advertised and wondered, But what on Earth would I do there? As it turns out, plenty. First, drop your carry-on at the 90-year-old Park Plaza Hotel (from $155; 307 South Park Ave.; parkplazahotel.com) in the budding art exurb of Winter Park. Load up on organic vegan grub at Dandelion Communitea Café (618 N. Thornton Ave.; 407-574-8313), chased with a handspun strawberry milkshake ($7) from Bananas Modern American Diner (924 N. Mills Ave.; 407-480-2200), before raiding the psych, punk, and garage bins at Vinyl Richie’s Wiggly World of Records (2436 E. Robinson St.; 407-864-2231) in the increasingly hip Milk District. Also rather Williamsburgian in spirit: the renovated Sandwich Bar (2432 E. Robinson St.; 407-421-1670), which hosts a sock hop every Monday; the Falcon (819 E. Washington St.; 407-423-2788), a multiuse space run by a couple that serves booze, showcases art, and screenprints T-shirts; and festive Tasty Tuesdays (facebook.com/tastytuesdaysorlando), a “food truck block party” shilling empanadas and artisanal ice pops.