Orlando After Dark

Cocktails, jazz, and the city that doesn't sleep

2.5h

Duration

1.5 mi

Distance

Stops

easy

Difficulty

$4.99 per person · one-time purchase

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About This Tour

When the theme parks close and the tourists retreat to their hotels, a different Orlando wakes up. This is the city locals know — a constellation of rooftop bars, hidden speakeasies, live jazz venues, and late-night eateries clustered in downtown's Church Street and Wall Street Plaza districts. This evening walk takes you through Orlando's best after-dark neighborhoods, from craft cocktail lounges to dive bars with more character than a Hemingway novel. Best started at sunset, finished whenever you're ready.

Tour Route Map

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7 stops · 1.5 mi walking route

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Preview (2 of 7 stops)

Church Street Station

Where Orlando's nightlife began — the restored Victorian train station that launched a thousand nights out.

"Church Street Station was the reason people came to Orlando before Disney existed. In its heyday, this Victorian train station complex hosted concerts, dance halls, and bars that drew crowds from across the Southeast. The buildings have been reborn — again — as the anchor of downtown's nightlife revival."

Hanson's Shoe Repair

Ring the bell, give the password, and step into Orlando's worst-kept secret — a Prohibition-era speakeasy that takes its cocktails very seriously.

"The sign says shoe repair. There are no shoes. There is a doorbell, a tiny window, and — if you know the password — a dimly lit bar where the bartenders wear vests and the cocktails take four minutes to make. Hanson's doesn't hurry. Neither should you."