Florida Keys With Kids: Our Road Trip to Key West
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After two days of alligators, airboats and exploring the Everglades, it was time for a complete change of scenery.
We packed everything back into our extremely practical family car – our red Mustang convertible – and started driving south.
Next destination: the Florida Keys.
I’d seen pictures of the Keys before our trip, of course. Turquoise water, endless bridges, palm trees and Key West sitting right at the end of the road.
It looked good.
Visiting Key West with kids was one of the parts of our Florida road trip I was most looking forward to.
What I didn’t expect was that somewhere along that road we’d find what is still, to this day, one of my favourite places in the world.
But first, lunch.
Our First Taste of the Florida Keys
Our first proper stop was in Key Largo, where we had lunch at Buttonwood Grill.
This was also where the Keys started to feel different.
Houses standing high above the ground, boats parked right next to them, water everywhere and that relaxed island feeling that becomes stronger the further south you drive.
We ordered some fish while the kids went for considerably safer American food.
Nothing revolutionary happened over lunch, but sometimes it’s these little moments that make a road trip: sitting outside, realising you’re finally in the Florida Keys and knowing the best part of the drive is still ahead of you.
Because our next stop was anything but normal.
Robbie’s of Islamorada – Tarpon, Seagulls & Unexpected Visitors
If you’re driving through the Florida Keys with kids, Robbie’s of Islamorada is one stop I’d absolutely make again.
The main attraction here is feeding the enormous tarpon that gather around the docks.
You buy a bucket of fish, walk out onto the dock and hold one over the water.
Simple.
Except the tarpon are HUGE.
And apparently you’re not the only one interested in your bucket of fish.
The local seagulls have perfected the art of stealing lunch directly from tourists, so half the experience became feeding tarpon and the other half became defending our fish from aerial attack.
While we were there, we even spotted a shark in the water.
And then some manatees appeared as well.
At this point we’d seen manatees for the first time only a day earlier in the Everglades, and suddenly Florida seemed to have them everywhere.
Robbie’s itself is just a fun place to wander around. It’s colourful, slightly chaotic and exactly the sort of roadside stop that makes a road trip memorable.
Before leaving, we added our own little mark to the place.
Inside the bar, the walls are covered with signed banknotes left by visitors from around the world.
So naturally, we signed one too and added it to the collection.
Maybe it’s still there.
Finding it again sounds like a perfectly reasonable excuse to return.
Sleeping Halfway Down the Keys
From Islamorada, we continued south toward Marathon, where we’d booked Kingsail Resort for the night.
It was another classic American motel.
Was it luxurious?
No.
Was there anything particularly memorable about it?
Also no.
But it was perfectly fine for what we needed: somewhere to sleep in a good location before continuing to Key West the following morning.
And that was actually a decision I’d make again.
Staying around Marathon breaks up the drive nicely and means you don’t have to rush through the Keys just to reach Key West.
The next morning, we simply jumped into a considerably emptier Mustang and continued south.
And then came Seven Mile Bridge.
Driving Seven Mile Bridge
There are roads you drive because you need to get somewhere.
And then there are roads that become part of the holiday themselves.
The drive across Seven Mile Bridge is definitely the second kind.
Water on both sides, tiny islands in the distance and this incredibly long strip of road stretching out in front of you.
With the Florida sun above us and Key West getting closer, this was one of those moments where the Mustang suddenly made perfect sense.
Eventually, the road ran out.
We had reached Key West.
Key West – Love at First Walk
We left the car near Fort Zachary Taylor and decided to explore the city on foot.
And Key West just clicked with me. Well, us.
Almost immediately.
We found the famous Mile Marker 0, wandered through the streets, walked towards the waterfront and basically stopped worrying about checking things off a list.
That’s probably what I loved most about Key West with kids.
You don’t really need to do anything.
Colourful wooden houses, tropical plants, old buildings, bars, boats and people wandering around with absolutely no hurry to be anywhere.
And chickens.
Lots of chickens.
Roosters casually walking through the streets as if they own the place somehow fit Key West perfectly.
We walked past Ernest Hemingway’s house, explored the waterfront and, obviously, tried Key lime pie.
You can’t come all the way to Key West with kids and not eat Key lime pie.
I think that’s probably illegal.
Somewhere during all that walking, Key West quietly became one of my favourite places I’d ever visited.
Not because of one huge attraction.
It was simply the feeling of the place.
If someone asked me today which place from our Florida trip I’d most happily return to just to spend a few days doing absolutely nothing…
Key West. Easy.
Swimming in February
Later we collected the Mustang and drove over to Smathers Beach.
It was February.
The beach was almost empty.
Coming from Europe, swimming in the sea in February isn’t exactly something we’re used to.
But the water looked far too inviting not to try.
So I went in.
And honestly? It was completely fine.
There was something slightly ridiculous about standing in warm Florida water in February while looking back at an almost deserted beach.
Meanwhile, everyone back home was dealing with winter.
I could get used to this.
Southernmost Point – Yes, We Took the Photo
From Smathers Beach we continued to probably the most famous photo spot in Key West:
the Southernmost Point buoy.
It’s colourful.
It’s iconic.
And yes, there’s a queue of people waiting to take exactly the same photo.
Did we join them?
Of course we did.
Sometimes you just have to accept being a tourist.
After getting the obligatory photo, we headed back towards the centre of Key West.
This time we left the car in a parking garage.
Because we had one more thing we wanted to see.
Sunset in Key West
If you’re spending a day in Key West with kids, stay for sunset.
We walked back towards the waterfront and joined everyone gathering near the pier.
The atmosphere completely changed as the sun started going down.
Street performers appeared, people gathered along the water and everyone seemed to stop whatever they were doing for a while just to watch the sky.
After a full day of walking around Key West with kids, swimming, eating pie and meeting more chickens than expected, it was the perfect ending.
We finished the evening with dinner around Duval Street before getting back into the Mustang for the drive north to Marathon.
I’ll admit, leaving Key West wasn’t easy.
I could happily have stayed.
One Last Florida Keys Roadside Stop
The following morning we had somewhere very different to be.
Our cruise was leaving Miami, which meant it was time to say goodbye to the Keys and drive north.
But Florida wasn’t quite finished with the roadside attractions yet.
On the way, we stopped for a photo with Betsy the Giant Lobster in Islamorada.
Because apparently when you see a gigantic lobster beside the road, you stop.
Those are the rules.
Then it was time for the long drive back to Miami.
We returned our Mustang – somehow with all our luggage still accounted for – grabbed an Uber and headed towards the cruise port.
The road-trip part of our Florida adventure was temporarily over.
Next stop:
the Bahamas.
Would We Visit the Florida Keys With Kids Again?
Without hesitation.
The Keys ended up being one of my favourite parts of our entire Florida trip.
The drive itself is beautiful, there are fun stops like Robbie’s along the way and there’s enough wildlife to keep kids interested even when you’re spending quite a lot of time in the car.
But Key West with kids was the highlight for me.
Looking back, the biggest thing I’d change is simple:
I’d stay longer.
We managed to see a lot in one day, but Key West isn’t somewhere that needs to be rushed.
Next time I’d spend at least a couple of nights there, forget about the itinerary for a while and just enjoy it.
Preferably with another slice of Key lime pie.
And probably another sunset.
FAQ: Florida Keys & Key West With Kids
Are the Florida Keys worth visiting with kids?
Absolutely. Our kids enjoyed the wildlife, feeding tarpon at Robbie’s, the beaches and all the unusual stops along the road. The drive is long, but breaking it up with stops makes it part of the experience.
How long should you spend in the Florida Keys?
We spent one night in Marathon, a full day in Key West with kids and another night in Marathon before returning towards Miami. It worked, but I’d recommend adding at least one more night, especially if you want to properly enjoy Key West.
Is Key West good for families?
We thought so. It’s very walkable, colourful and relaxed, and there’s plenty to see without constantly visiting paid attractions. Our day was mostly spent walking, eating, exploring and enjoying the atmosphere.
Is the drive from Miami to Key West worth it?
Yes – and don’t treat it simply as transportation. The Overseas Highway, Seven Mile Bridge, Islamorada and the smaller Keys are part of the experience. Give yourself plenty of time for stops.
Is Robbie’s of Islamorada worth stopping at?
For us, definitely. Feeding the tarpon was fun, the kids enjoyed it and we also saw a shark and manatees while we were there. Just keep an eye on your bucket of fish. The seagulls know exactly what they’re doing.
Can you swim in Key West in February?
I did! The water at Smathers Beach was comfortable enough for me to swim, although the beach itself was surprisingly quiet. Weather and water temperatures obviously vary, so don’t take my February swim as a guarantee.
Where should you stay between Miami and Key West?
We stayed in Marathon, which worked really well geographically because it’s roughly in the middle of the Keys. If I planned the trip again, though, I’d probably keep the Marathon stop and then add at least one night directly in Key West.
Is one day enough for Key West?
You can see plenty in one day – we did – but I don’t think it’s the best way to experience Key West with kids.
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