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Things to do in Key West at Night

Updated on: May 29, 2023 2:29:42 PM

Sunrise through Sunset...before, after and in between...there is always something happening in Key West.  At dusk and after dark, here is a list of things to do in Key West at night.

On Land

Just before the warm island sun sets to light up the sky with breathtaking color, visitors and residents alike gather at Mallory Square, located at the western edge of the island for the world renowned Sunset Celebration.  A one of a kind celebration that pays tribute to the Sun... center of our solar system that holds it all together.

 This nightly arts festival delights attendees with street performers, local artists, magicians, psychics  and plenty of food & beverage carts satisfy your appetite that only arrive to this popular destination at dusk.   

Many claim that Mallory Square Dock is the best place to watch the sun sink below the edge of the world.   We certainly won't disagree! Fireeater-piqsels.com-id-jhnbuPhoto Credit: piqsels.com!

On the Water

If you prefer your sunset experience floating atop the crystal blue waters of Key West,  several charter services offer sunset celebration cruises.  So, pull anchor away from those landlubbers and toast to the close of yet another mesmerizing tropical day in paradise, on the open waters.

Whether by motor or sailing vessel, a few companies welcome guests aboard to celebrate the sunset on the tropical waters of Key West.  There are elegant dinner type cruises and more casual beach type cruises, that all include a menu of food and beverages, while  some include music to dance the night away.

Things to do in Key West

Now that we've suggested some twilight hour activities,  Key West takes on a completely different glow in the truly after dark activities. Out of the mainstream after dark...here we go. 

Night Kayaking

You may be familiar with kayaking and glass bottom boating but "extremely cool not creepy" is how  Paddle Key West describes night kayaking.  We agree...extremely cool!  Explore the underwater beauty of Key West through clear bottom kayaks illuminated with LED lights. This one of a kind guided experience is a tranquil way to explore the mangrove creeks, surrounding nature and underwater world.

Kayaking at NightPhoto Credit: KeyWestPaddle.com

Drag Shows

 Key West is wildly popular for its great entertainment, creative artists and dreamers. Amazing costumes and performances that would be the envy of any Broadway performer make going to a drag show a must do while in Key West.   For an evening of comedy, song and dance that you won't readily forget, this one is for you.  There are various venues and productions to select whichever strikes your fancy.

Ghosts & Gravestones Tour

If you're really looking for the haunting, spooky side of island life, then the Ghost & Gravestones Tour is just your ticket to fright. Hop on board their ghastly/ghostly bus as your costumed ghost hosts guide you on an unusual narrated tour of spooky and scary truths of  Key West, formerly named "Bone Island".  Meet Robert the Doll, purported to be the most haunted toy, or the Lady in Blue that haunts Captain Tony's Saloon, where she was executed. 

ghost-and-gravestones-key-west-shipwreck-600x580Photo Credit: Old Town Trolley Key West


For a couple of options a bit more on the tamer side of life, you might consider the Key West Theater or the Tropic Cinema. The theater is a live entertainment venue, hosting top touring acts, comedians and big name musical groups. The cinema is the islands own art deco style theater; presenting indie films, documentaries and blockbuster cinematic movies.

Key West Express

We can all agree to disagree but we really do have some of the best sunsets you can behold, even on our journey home from Key West. Have you ever experienced the "Green Flash"? On the water? Well, now's your opportunity to get out and see it. Book your Key West adventure and enjoy all that Key West has to offer.

Hero Image Photo Credit: piqsels.com

Topics: Insider, Attractions, Activities, Restaurants, Outdoor, Tours, Drag Show, Night Life, Information

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