It’s only a couple of blocks this way and that, but Hannibal Square packs a lot into a small area. It’s a picturesque spot for brunching, strolling and window shopping, not to mention it’s just a quick hop from Park Avenue (see page 45) with even more classy joints. This is the kind of mossy, live-oaked neighborhood where the servers won’t kick you out if you’re sitting on the patio for two hours gossiping with your buds over mimosas and snacking strawberries out of your farmers-market haul. Just leave the Louboutins at home – the cobblestone streets aren’t stiletto-friendly.
Armando’s Cucina Italiana and Pizzeria
463 W. New England Ave., Winter Park
553 W. New England Ave., Winter Park
535 W. New England Ave., Winter Park
433 W. New England Ave., Winter Park
Hannibal’s on the Square
511 W. New England Ave., Winter Park
Rifle Paper Co.
558 W. New England Ave., Winter Park
Hannibal Square Heritage Center
642 W. New England Ave., Winter Park
Winter Park Farmers Market
7 a.m.-1 p.m., Saturdays
200 W. New England Ave.
Saturday farmers market with food vendors, local honey and cheese, plants and produce.