Winter Park is a historic neighborhood in Orlando. The area is home to a string of popular lakes, a beautiful downtown area (buzzing with storefronts, restaurants, and al fresco dining), and lush parks where families relax and soak up the warm weather together.
Prato, a modern Italian restaurant, sticks to the seasons with fresh ingredients. The interiors are warm and inviting with plenty of exposed brick and floor-to-ceiling windows that bring in natural light. Dine on house-made ricotta crostini, potato gnocchi with truffle butter, and veal milanese while sipping on a glass of wine.
DRINK: The Wine Room on Park Avenue
Calling all vino lovers: there are over 150 hand-picked wines at this venue, available in 1, 2.5, or 5 ounce pours. The tasting room—which also includes a cheese shop, restaurant, and wine bar—uses extra fancy Enomatic dispensing machines to pour samples from its vast wine collection, allowing you to try plenty of bottles without visiting the bar each and every time. Taking a bottle home? Don’t skip the venue’s spread of meats and cheeses for no-brainer pairings.
There are six lakes in Winter Park, each connected through a network of canals. There’s a handful of ways to hop on these waterways as a visitor (paddleboarding, kayaking, and more), but the easiest option is the Winter Park Scenic Boat Tour. The journey whisks you past historic homes (including the former home of Mr. Rogers) on an hour-long tour guided by local drivers with plenty of stories to tell.
STAY: The Alfond Inn
The Alfond Inn is a boutique hotel that's surprisingly owned by the local Rollins College. Flexing the definition of liberal arts, the hotel has a rather sizable collection of contemporary and museum-worthy art throughout the property, not to mention spacious rooms and chic common areas. The on-site restaurant, Hamilton’s Kitchen, serves riffs on Southern fare—it’s a great spot for a quick breakfast before you head out for the day.
If you do just one thing…
Head to the West Meadow in Central Park for the Winter Park Farmer’s Market. The outdoor market runs every Saturday from 8am to 1pm, and it’s your best chance to get hyper-local goods from dozens of vendors and nearby farms (think fresh produce, cookies, honey, candles, and more).