Because childhood memories should include cannons, ghosts, and butterflies that could be spies
Key West is that uncle at the family reunion. He’s charming, unshaven, slightly tipsy and loaded with stories the kids shouldn’t hear but definitely will. The same one that will somehow hit on the youngest non-relative available, tell a joke that’s slightly racy, ask your dad for a quick loan and make your mom go, “God, I really dodged a bullet there.” The type that regardless of it all, regardless of the fact that midway someone said “we will not invite him again,” somehow pops up again next year cause: “the kids just love him.”
In this guide
- Fort Zachary Taylor – cannons and sunburns
- The Butterfly & Nature Conservatory – Disney, but real and winged
- Meet Robert the doll – nightmares, guaranteed
- Conch Tour Train – the locomotive of parental sanity
- Key West Aquarium – sharks, turtles and questionable tank sizes
- Key West Shipwreck Museum – a scavenger hunt with ghosts
- Sunset Celebration at Mallory Square – clowns, cats and Chaos
Key West is paradise, yes. But paradise with quirks, skeletons and a long rap sheet. And yet, weirdly enough, it’s also a perfect playground for kids.
Why? Because in Key West, everything looks like it was designed by Dr. Seuss on Bacardi. There are fortresses, doll curses, butterfly kingdoms and roosters that strut like they own real estate portfolios. The kids won’t even realize that they are learning history, biology and also why you should never taunt the dead.
It’s a bizarre place. A place that after being propped up, someone from the Chamber of Commerce said, “And what are the kids supposed to do?” So, in order to attract the family crowd, they started to improvise.
Like adding a petting zoo next to an alligator enclosure. Or thinking that a swing set goes hand in hand with a bike bar. And somehow, amid that bivouac copy paste fantasia, things sort of clicked in. Here’s the lineup.
Your kids in Key West
1. Fort Zachary Taylor – cannons and sunburns
Drag your offspring to a Civil War-era fort where the cannons are still lined up like they’re waiting for the Confederacy to come back. It’s part military history, part hide-and-seek heaven.
You can picnic, you can swim, you can march your kid along the ramparts screaming “AVAST, YE SCURVY DOGS!” until strangers glare.
Bonus: the beach here is one of the prettiest in Key West, and the fish nibble your toes if you stand still long enough.
Why bring the kids? Because kids love forts and play weapons. And you can tell them the moat is filled with invisible alligators to keep them from wandering too far.
Also, the guided tours are a blast. In what way? They don’t skimp out on the gory details. “So, here’s where they started creating funky cannon balls. Less balls, more missiles so they were more aerodynamic and could be better aimed. Once, they could plug one of those up a pirate’s a**… I mean posterior…”
2. The Butterfly & Nature Conservatory – Disney, but real and winged
It’s a glass-domed jungle filled with over 50 species of butterflies and tropical birds. Imagine hundreds of delicate winged creatures landing on your kid’s head while flamingos strut like pink security guards in the background.
You only see that in Disney cartoons or when your friend Mike comes at you with gummy bears he scored at the local CBD store.
There’s even a gift shop where you can buy butterfly-shaped tchotchkes that will sit in your house forever, silently reminding you that “You need to get your finances in order, man. Did you really spend $20 bucks on me?”
Why bring the kids? Because it’s magical, and also the best place to get an Instagram photo that makes it look like your family is wholesome. Ignore the fact that five minutes later your child will throw a tantrum over ice cream and that your husband is having a fit trying to hide that fact that he keeps staring at the waitress in the bikini.
3. Meet Robert the doll – nightmares, guaranteed
Yes, the haunted doll. The one that inspired Chucky. Yes, the one you have to ask permission before taking a photo or risk a curse that follows you all the way back to Tempe.
Robert lives in the Fort East Martello Museum, and he looks like he crawled straight out of a Stephen King brainstorming session. Your kid will either:
a) Laugh nervously and bolt for the exit, or
b) Stare into Robert’s button eyes and whisper, “He talked to me.”
Either way, it’s a childhood memory etched in fire.
Why bring the kids? Because nothing bonds a family like intergenerational trauma. And because “haunted doll” makes for better show-and-tell than “I built a sandcastle.”
“What did you do this summer, Tommy?” “I tussled with the forces of Hell and came out unscathed.”
Teacher turns to parents.
“And don’t get me started on when they took us to the house of the guy that embalmed his wife and lived with her in unholy matrimony for years.”
4. Conch Tour Train – the locomotive of parental sanity
Climb aboard the Conch Tour Train. It’s a chugging, open-air trolley that rolls around Old Town with a conductor who sounds like he drank four Cuban coffees before the shift. It’s cheesy and it’s touristy. So, it’s just right.
You’ll pass landmarks, get the history (pirates, poets, presidents and cocaine cowboys). But most importantly – you’ll be sitting down in the shade.
Why bring the kids? Because they love trains. You love not walking. And you can come aboard with a hallowed out pineapple with enough lighter fluid to help a jet take off. Everyone wins.
5. Key West Aquarium – sharks, turtles and questionable tank sizes
This isn’t SeaWorld. It’s small, scrappy and oddly weird, in a charmed induced kind of way. The touch tanks let your kid hold a sea star, while the shark feedings let them watch something get ripped apart at close range. Teachable moments.
Why bring the kids? Because nothing says “educational family vacation” like your child shrieking while a shark named Old Smokey chomps down on his lunch. Little sociopath. And yes, your husband seems to also be shrieking in delight, so it’s a genetic quirk – you really should get that checked out.
6. Key West Shipwreck Museum – a scavenger hunt with ghosts
This one’s half history lesson and half haunted-house theater. And better, of course, for the older kids.
Actors in 1850s garb tell you about salvaging shipwrecks, then lead you through shadowy halls filled with artifacts and mannequins that definitely move when you’re not looking.
And some ghost tours even come in at night. So, imagine if it’s scary in broad daylight. At night, think horror movies, and not those wussy ones like “The Conjuring.” I’m talking full blown horror/slasher… 2001, “Thirteen Ghosts.”
The best part? The 65-foot lookout tower. March the kids up the stairs, let them spot Cuba (not really, but they’ll try), then watch them sprint back down while claiming “something touched me.”
Why bring the kids? Because it’s equal parts creepy and cool. And because climbing a tower wears them out, which means earlier bedtime for you.
7. Sunset Celebration at Mallory Square – clowns, cats and Chaos
Every night, Key West gathers at Mallory Square to watch the sun drop into the ocean like a flaming coin. But before the sunset? It’s a carnival. Sword swallowers, jugglers, fire dancers and folks that improvise things: “My iguana, Charlie, knows the foxtrot.”
Incredibly, there’s a a man whose trained cats jump through flaming hoops. Yes, cats. Jumping. Through. Fire.
Why bring the kids? Because the circus vibe is free, the popcorn is cheap, and the sunset looks like God spilled Jose Cuervo sunrise across the sky. Also, again, in case it didn’t sink in: Cats. Jumping. Through. Fire.
Cry havoc and let slip the Dogs of War
Forget Disney. Forget Legoland. Key West gives your kids what they really want: haunted dolls, forts, sharks, trains and cats committing arson.
There’s a reason why “Scary Stories To Tell In The Dark” with those nasty Stephen Gammel drawings, is such a hit. Yes, they’ll go gaga for “Frozen.” But give them a sketch of a girl with spiders crawling out of a pimple in her face, and they’ll explode in a frenzy of joy.
They’ll whine, they’ll cry, they’ll beg for another snow cone… but years later, they’ll say:
“Remember when you made me meet that haunted doll?” “Remember the cats and the fire?” “Remember when you told me the fort moat had alligators?”“ Remember when you hit dad over the head and screamed ‘Kent, she’s half your age! Stop looking!”
And you’ll smile, sip your concoction, and say:
“Yes, kiddo. That’s Key West. And it made you stronger. Also, it’s where we meet Mike, abs for miles. Remember to tell dad when you see him to send over his monthly check.”
Have you taken your kids to Key West? Where did you take them? Let us know in the comments!