See a very weird play
Mad Cow Theatre
For two weeks each year in May, Orlando becomes home to zaniest theater in the U.S. That’s because the city hosts the Orlando Fringe Festival. The event boasts dozens of unique and uncensored artists and theater acts. Past productions have included a Shakespearean version of Ghostbusters, a musical that takes place completely in a sauna, and a rapping rendition of Dr. Jekyll and Mr. Hyde. If you can’t make it to town during the festival, the local Mad Cow Theatre is usually staging some sort of interesting production all throughout the year.
Catch the sunset from a rooftop
The Orlando area’s frequent showers are annoying but often result in stunning sunsets. The vistas are best appreciated from about 80 feet above sea level on one of Orlando’s many rooftop venues. While a few downtown bars spill out above the cityscape, the most magnificent, unobstructed view is found at Reunion Resort’s Eleven. The bar-restaurant is located on the—you guessed it—11th floor. If you time it right, you can catch a glimpse of Magic Kingdom’s nightly fireworks with a martini in hand.
Freak out at Spook Hill
When visiting Orlando, or anywhere in Florida really, it’s hard to escape the Sunshine State’s trademark weirdness (Case in point: The Skunk Ape). But one urban legend actually worth exploring is Spook Hill, a rural stretch of road about an hour outside of the city where visitors park their car in neutral and are amazed as the vehicle appears to roll uphill without any assistance. Legend says the supernatural site was created during an epic battle between a Native American tribal leader and a massive alligator. It’s probably just an optical illusion, but you can tell your friends back home that you were possessed by a ghost.