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!
It’s not everywhere that the transition of day into night is a cause for celebration. Then again, Key West takes pride in doing things just a little differently.
Located on the southern tip of the island, this large waterfront plaza is a huge draw and was declared “among the top places to visit in Key West” by Thrillist. You’ll find circus performers, musicians, a great Cuban restaurant, several markets to pick up some one-of-a-kind Key West souvenirs and an influx of people coming and going on the many cruise ships that enter through the nearby port. This is also the place, designated by locals, that traditionally hosts the daily Sunset Celebration. This family-friendly nighttime event brings together a great many people and makes for an evening of community by the water. Cheer on the sun as it dips into the ocean, leaving behind dazzling streaks of color in the dusky sky. The square is also used to throw special events throughout the year, and it’s also in close proximity to eight of Key West’s top resorts. Here are a few other places worth a visit while in Mallory Square.
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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:
The first stop is at the Key West Shipwreck Museum, where guests will hear ghostly tales and have the chance to hold a bar of silver. At the Key West Shipwreck Museum, you’ll see firsthand how the wreckers lived and the results of their efforts to save the crew and the ships that crashed while sailing into the island.
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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Originally built in 1848 as the First Baptist Church of Key West, this renovated multiplex-style venue is the island’s premier performing arts center.
Its long history as a former church, dance club and concert venue can still be felt the minute you set foot inside. The gorgeous vaulted wooden ceilings, vintage candelabras and cabaret-style seating lend an elegant, old-timey feel. There’s a delightful balcony bar where you can sip on a pre-show cocktail overlooking Eaton Street. The table service here is excellent, but so is every other aspect of this place. Great warm acoustics, family-friendly atmosphere and, of course, top-tier talent from all over the world keep patrons coming back for more! The theater is also home to the Key West Theater Recording Studio: a fully equipped, professional recording environment that provides a full host of recording services, from live recording to voice-overs. The on-site rehearsal space also doubles as a great place for meet-and-greets and special events.
The Key West Theater is also instrumental in bringing the joys of music to students by hosting Living Music, a nonprofit outreach program that works in concert with existing music curriculums to enrich the lives of kids from 1st to 12th grade.
If you’re in the market for a fine acoustic or electric stringed instrument to unleash your inner rock star, pay a visit to The Grateful Guitar. Since 2012, this boutique guitar shop, located right inside the theater building, has been providing the six-string community with the finest new and used instruments, amplifiers, rentals and accessories. Want to brush up on your chops? The shop also provides private instruction for all skill levels.
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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!