The best neighborhoods in Orlando

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.

EAT: Prato 

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.

DO: Winter Park Scenic Boat Tour

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).

Although it’s a touch farther than other neighborhoods (it’s just west of Orlando), Winter Garden pulls out all the stops. The quaint neighborhood looks straight out of a movie thanks to its downtown, a charming spot that’s actually listed on the National Registry of Historic Places.

EAT AND DRINK: Plant Street Market

Plant Street Market, a buzzing food hall attached to a craft brewery, is a popular local hangout with 20 different vendors. Here, you’ll find purveyors who specialize in anything from macaroni and cheese to sushi, BBQ, and coal-fired pizza. Don’t skip the adjoining Crooked Can Brewing Company for seasonal brews, and don’t be afraid to head outside where a shaded patio offers an al fresco dining moment.

DO: West Orange Bike Trail

Yes, it’s called the West Orange Bike Trail, but even if you’re keen to run or walk, hop on this 22.26-mile route and work up a sweat. The trail cuts right through the bustling downtown, which means you can stop for a bite or drink if that’s more your speed.

STAY: Airbnb

There aren’t many hotels near this neighborhood, and most are very expensive. Luckily, there are well over 100 Airbnb listings up for grabs—it's a great way to stay in the neighborhood, especially if you opt for a rental with a private pool (hey, you only live once).

If you do just one thing…

Be sure to walk around downtown Winter Garden. The area is oh-so-charming with shops, restaurants, and a historic vibe that’s hard to beat.

Lake Nona, a newer neighborhood not far from the airport, has quickly found its identity as a haven for younger, active locals. As a mixed-use development, the community has the sort of built-in features you might expect (good food, live music, and plenty of fitness-oriented facilities), and the residents are all the more happy as a result.

EAT: Chroma Modern Bar and Kitchen

Head to Chroma Modern Bar + Kitchen if you’re dining with your crew—the restaurant is known for its shareable menu. Dishes like charred shishito peppers, crispy pork belly pad thai, and cheeseburger sliders are certainly crowd-pleasers. The restaurant has three main sections: a lively bar, a softly lit dining room, and a smaller (but brighter) dining room that’s surrounded by windows.

DRINK: Park Pizza and Brewing Company

Sure, it’s hard to say no to wood-fired pizza, but that’s not the only reason locals love Park Pizza and Brewing Company. Here, you’ll find a great selection of small-batch craft beers—the Belgian Wit and Standard Lager are two favorites—that pair great with pizza but stand perfectly well on their own, too. The beer selection changes often with plenty of seasonal brews, so you’re likely to find a different lineup each time you visit.

DO: Boxi Park

Just steps away from Park Pizza and Brewing Company is Boxi Park, a unique hangout with a food truck-style setup and ample outdoor space. Each vendor operates out of a repurposed shipping container, and the options range from burgers to lobster fries and fancy soft serve ice cream. Grab a sweet or savory bite to eat, take part in a weekend pick-up volleyball game, or just enjoy live music while dancing under the stars.

STAY: Airbnb

As this is a fairly new neighborhood in Orlando, your best bet is to book an Airbnb, or stay in another neighborhood and drive to Lake Nona for the day.

If you do just one thing…

We know there are other amusement parks you’re hoping to see, but Nona Adventure Park offers something entirely differen. Right on Lake Nona, an over-water inflatable obstacle course (totalling 1,000 feet) is a bouncy blast for kids, while other activities like wakeboarding and climbing (there’s a massive ropes course) will keep adults entertained, too.

Downtown Orlando means business, and that’s no understatement. The neighborhood is home to some of the best restaurants in Orlando, and it’s certainly the go-to spot for nightlife and culture. Out of all the places to see and be seen, you can even ride a massive swan-shaped boat on Lake Eola in the heart of downtown—if that doesn’t make you smile, we don’t know what will.

EAT: Reyes Mezcaleria

Reyes Mezcaleria isn’t your typical fast-casual Mexican joint. The head chef, Wendy Lopez, uses traditional methods of Mexican cuisine to create a robust menu with dishes like fresh ceviche (made with seabass, shrimp and octopus), gooey queso fundido (plumped up with housemade chorizo verde), and a fantastic chile relleno stuffed with beans, cheese, and corn.

DRINK: The Courtesy

The Courtesy made a name for itself as the first true craft cocktail bar in Orlando. The menu here changes three times a year with an emphasis on seasonality, while a few signature drinks stick around—give their rotating clarified milk punch a whirl, and we promise you won’t regret it.

DO: Lake Eola Park

While Lake Eola Park is home to plenty of real swans, you can play the part by getting out on the water in a large swan-shaped paddle boat. Is it cheesy? Of course it is. But after taking a spin around the tree-lined lake, we have a feeling you’ll leave with a smile.

STAY: Aloft Orlando Downtown

Stay right in the middle of the action at Aloft Orlando Downtown. The hip hotel is all about the location—it rubs shoulders with some of the best restaurants and popular bars in Orlando, and it’s a short drive to other popular attractions (yes, we’re talking about theme parks).

If you do just one thing…

Watch a show or performance at the Dr. Phillips Center for the Performing Arts. Catch tried-and-true holiday classics like The Nutcracker, or Broadway shows like Disney’s Frozen.