The City Beautiful: A Historic Downtown Orlando Walking Tour

Orlando is far more than theme parks and tourist attractions.

On this walking tour through downtown, you’ll discover the historic heart of a city that evolved from a frontier fort into Florida’s cultural center. You’ll explore Art Deco buildings that survived fires and economic downturns, Victorian structures transformed into speakeasies, and a scenic lake that began as an 80-foot sinkhole and became the city’s defining landmark.

The tour starts at the AC Hotel Orlando Downtown, steps from where the basketball team Orlando Magic plays. You’ll walk past the copper-domed City Hall, through the opulent Grand Bohemian Hotel with its world-famous Bösendorfer piano, and along Magnolia Avenue’s revitalized bar scene.

As you circle Lake Eola Park, you’ll find out how this sinkhole became Orlando’s postcard attraction with swans, a Chinese pagoda, and a choreographed fountain show. Along the way, you’ll hunt for speakeasies hidden behind doors marked “Private,” browse millions of cigars in an authentic shop, and decode public art installations. The tour ends at the Orange County Regional History Center, the 1927 courthouse where Ted Bundy was sentenced to death.

On this 120-minute tour, you’ll have a chance to:

• Browse over two million cigars at Corona Cigar Company, including rare pre-embargo Cuban hand rolls
• Find Hanson’s Shoe Repair speakeasy using a password from their Instagram stories
• Admire the Kress Building’s zinc-pressed metal siding imported from the UK in the 1920s
• See Cheyenne Saloon’s golden oak woodwork where Garth Brooks and Alan Jackson performed
• Pass historic churches, a restored Kress department store, and the building where Cubs shortstop Joe Tinker ran his real estate business
• Discover how 200 S Orange became Orlando’s tallest building at 441 feet with iconic green pyramids
• Visit the Chinese Ting pavilion that was built in Shanghai and reassembled at Lake Eola
• Get a discount at Cocktails and Screams by wearing a costume any night of the year

This tour reveals downtown Orlando’s personality beyond the theme parks, complete with speakeasies, history, and a surprising Shakespeare connection.