The Kessler Collections

Discover Orlando’s Grown Up Side

As one of the most popular travel destinations in the U.S., Orlando is often synonymous with theme parks and larger-than-life characters. However, a lucky few discover there’s a reward in straying from the attractions, the thrills and all the manufactured fun. Orlando, better known to locals as “The City Beautiful” is a cultural gem offering surprises for even the most seasoned and curious travelers.

To make the most of your visit, head straight to the brick-paved, tree-lined streets of downtown. Orlando’s metropolitan footprint is built around Lake Eola Park. A leisurely stroll around its glassy lake reveals a vibrant downtown dotted with classy accommodations, many with rooftop pools and stunning city views. A local favorite is the swank and artsy Grand Bohemian Hotel Orlando, which truly reflects the spirit of the city’s rich performing arts and museum scene.

The neighborhoods surrounding Orlando’s downtown are well known for their laid-back vibe and interesting historical homes. If you’re in the mood to stretch your legs, head east of Lake Eola and explore Thornton Park. This area of the city feels like a funky, old-fashioned suburb and boasts many of Orlando’s best cafés, hip galleries and trendy boutiques. And on the west side of Lake Eola don’t miss a visit to the City Arts Factory, housing one of the largest, most eclectic art collections in Orlando, including a wide variety of local and international pieces in all styles. The best part? Admission is free.

If you feel like trying something completely different, set your sights northeast of downtown and head over to the East End Market. This bohemian, free-spirited marketplace is a collection of the best local purveyors of baked goods, food, art and produce. Bring your appetite and plan to spend a few hours sampling locally grown produce, wine, craft beer, coffee, fresh-pressed juice, pastries and more.

Before you turn in for the night, be sure to check out Church Street Station, the epicenter of Orlando’s bustling nightlife scene. Church Street Station is one of the most historic parts of the city, built around an old Railroad depot, originally constructed in 1889. The depot still stands—an iconic reminder of Orlando’s humble beginnings. If you’re in the mood for a classy night alfresco, head to One80 Grey Goose Lounge, one of the city’s best rooftop bars. If you’re looking for something more low-key, Native Social Bar delivers cocktails, live music and a more relaxed scene. And if you’re looking for a show, check out The Beacham, a converted 1920s building turned concert hall. Wherever you spend the night, soak in the surroundings.