No matter where you live or what you do, time seems to escape us. How many times have we referred to "time flying". Despite our best intentions, popular destinations and points of interest in our own backyard that are enjoyed by visitors are always on our "things to do and see list". One of the most common phrases we hear, at Key West Express is... " I've lived in Florida for XX number of years, but I've never been to Key West." Yes, we get it but, "Why NOT? What are you waiting for?" A staycation to Key West is just what the "ho-hum" doctor ordered.
Key West does not slow down when the sun disappears. The island simply changes moods. Sunset crowds gather along the waterfront, live music spills onto Old Town streets, historic buildings become the setting for ghost stories, and illuminated kayaks glide through dark mangrove creeks.
The best things to do in Key West at night include the Mallory Square Sunset Celebration, sunset cruises, live music on Duval Street, drag shows, ghost tours, night kayaking, waterfront dining, theater performances and relaxed walks through Old Town. Most evening attractions are concentrated around Mallory Square, Duval Street and the Historic Seaport, making it easy to combine several experiences in one night.
AQUA Bar and Nightclub, Key West
A visit to Key West is incomplete without taking in a Drag Show!
Shows at Aqua are fun, sharp, sometimes raunchy and a classic part of the Key West experience. Either grab a seat up by the stage or in the shadows in the rear, you are bound to have a roaring good time. The dynamic, high-energy cast create a fascinating and memorable evening, as they perform to famous tunes and outlandish celebrity impersonations!
There are plenty of places to watch a ball drop. Key West, naturally, has a few more colorful ideas. On Thursday, December 31, 2026, you can ease into the evening with a famous sunset, then ring in the new year with a giant red shoe, a glowing conch shell or a pirate wench descending from a schooner mast—all within a short Old Town walk of one another.
That wonderfully odd mix is exactly why New Year's Eve here is so much fun. The air is warm, the streets are lively and a simple midnight countdown turns into a story you will be telling long after you have traded flip-flops for winter boots. The island's current New Year's Eve event guide confirms the big three celebrations, but individual venue details can change, so check the official pages before you head out.
