When evening descends on the Conch Republic, a festive atmosphere permeates the air, and natives and visitors alike take to the streets for something fun to do at night. Because of its relatively small size, this island enclave is ideal to explore on two feet or two wheels. With many of its popular attractions within close proximity of one another, Key West is an easy and highly accessible town with plenty to offer when the sun goes down. Though Key West has a well-earned reputation as a party capital, with a robust nightlife packed with bars and a vibrant live music scene, this part of the world also has plenty to offer those looking for family-friendly activities to do at night. To get the most out of your visit, check out our list below of the best things to do at night in Key West, guaranteed to put a smile on everyone’s faces!
Do you wonder if ghosts really exist? Do you appreciate a good jump-scare? If your curiosity leads you down the road of the paranormal, and you like a little horror with your history, climb aboard the Trolley of the Doomed for an old-fashioned family-friendly fright-fest!
You don’t have to be an amateur ghostbuster to enjoy the thrills and chills of a Ghosts & Gravestones tour. This unique family-friendly journey (recommended for children 13 and up) into the dark heart of Key West’s creepy past is a wonderful nighttime adventure of storytelling that will alter your perspective of what you thought you knew about this funky seaside city, with plenty of hair-raising scares for the whole family!
Equal parts spooky and kooky, Key West and its colorful history make up a place unto itself, and this tour captures that in all its ghoulish glory. Among the places you can expect to visit and learn about are:
Drive past this shallow gravesite on Higgs Beach discovered by workers in 1862 who were digging up the beach when the nearby Civil War-era West Martello Fort was under construction. It was here where almost 300 African slaves, liberated from a slave ship bound for Cuba by the U.S. Navy, were buried after they ultimately perished from disease and unsanitary conditions. It remains the only known African refugee cemetery in the United States.
Drive by the East Martello Fort and hear about Robert the Doll. According to legend, the seemingly innocent doll on display here once belonged to a local young boy around the end of the 19th century. From almost the outset, this doll terrorized the little boy by suddenly appearing at the foot of his bed or windowsill. When the doll was locked away in the attic many years later, supernatural phenomena continued to be reported by visitors to the house as well as its inhabitants. The doll is rumored to have been cursed by the servant who gifted the doll to the little boy as a consequence of her mistreatment by his parents. Today, the East Martello Fort, a Civil War-era garrison, is the home of Robert the Doll. This malevolent mannequin is still known to cause mischief. Apparently, he likes to meddle with camera equipment if you try to snap his picture without asking his permission first.
There are plenty of good scares on this family-friendly tour, and they are further enhanced by the presence of “Ghost Hosts,” costumed guides dressed in their spooky best, who provide entertaining narration throughout. Definitely a top pick for things to do at night!
Key West is one of the best places on earth to gaze longingly at a breathtaking sunset. Viewing the majesty of this natural spectacle, however, is even better when you do it from the water!
Once aboard Fury’s 45-foot, state-of-the-art catamaran, all you have to do is bring your island vibes, and they’ll take care of the rest. This family-friendly trip includes complimentary cold beverages for all ages, and you are free to bring aboard any munchies you desire for the journey (as long as they are not kept in a glass container). Your sail will take you past Mallory Square, Sunset Key and the Key West Harbor. As the curated playlist rocks along as your own personal sunset soundtrack, your every care will fade into the distance while the day gives way to night (and more family-friendly fun to come)!
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As you can see, when it comes to family-friendly things to do at night in the Conch Republic, your options are never lacking in the fun department. The Southernmost City is always ready to welcome, delight and entertain all, and it gets better and better with every passing year. Key West is a lot more than bar crawls and conch fritters (though those things are awesome, too)! Visitors from all over can have a rich, family-fun experience on this beguiling island, and we hope yours does too!