Rebecca McCamy's Sassafras Sweet Shoppe (sassafrassweetshoppe.com), a colorful candy boutique, fits perfectly in her idyllic hometown 15 minutes north of Orlando. Like Rebecca, several other locals have opened new shops that now join older attractions to turn the sleepy resort community into a vibrant vacation spot. "People think that all of Central Florida is just as crowded as the amusement parks," Rebecca says. "But Winter Park is different. It's relaxed without being slow paced."
Rebecca starts her day with a chocolate Bear Paw ($3) at Croissant Gourmet (croissantgourmet.com), a cozy cafe run by French-born pastry chef Francois Cahagne.
Rebecca's next stop is the ultra-feminine boutique Thread (threadwinterpark.com) to stock up on easy summer pieces such as Tory Burch tunics ($295) and Sam & Lavi eyelet shorts ($110). Then it's time for a dose of culture at Casa Feliz (casafeliz.us), a 1932 historic house museum that offers free tours on Tuesdays and Thursday from 10 a.m. to noon. Stop by on Sundays from noon to 3 p.m. for an open house and the "Music at the Casa" variety series. Designed by Chicago-born architect James Gamble Rogers II, the Andalusian-style masonry farmhouse was saved in 2000 after Winter Park residents raised more than $1 million to restore it. After touring the Casa, Rebecca drops by Cocina 214 (cocina214.com) for lunch. The Tex-Mex gem serves melt-in-your-mouth Brisket Tacos ($12) and lively Pop Rocks-rimmed margaritas ($10).
Rebecca's favorite place for afternoon drinks is the Park Plaza Gardens. The restaurant adjoins the Park Plaza Hotel (parkplazahotel.com)—a 28-room historic hotel anchoring Winter Park's main intersection. "Everyone there is so social that you'll often make fast friends with the table next to you," she says. "It's a great way to end a day on the town."