You’ll cruise Old Town Key West by bike with a local guide who knows every shortcut and story. Snap photos from coast to coast, laugh at chicken antics, and cool off with bottled water and real Key Lime pie. The ride is easygoing, full of unexpected details — it’s more about soaking up island life than racing anywhere.
I’ll admit, I was mostly in it for the Key Lime pie at first. But rolling into Old Town Key West on those bright bikes — you know, the ones with the squeaky bells — felt like stepping into someone’s sun-bleached memory. Our guide, Mark (who’s lived here longer than I’ve been alive), started us off near the Gulf. He kept pointing out these pastel houses with crooked shutters and telling stories about pirates and poets who somehow ended up here. The air smelled like salt and sunscreen, and there were chickens everywhere — I’m not kidding, they just strut around like they own the place.
We stopped at this spot where you can actually see both the Gulf of Mexico and the Atlantic if you squint past some palm trees. Mark made a joke about how it’s the only time you can say you biked from coast to coast in under two hours. I tried to snap a photo but my lens fogged up from the humidity — classic me. At one point we passed a guy selling coconuts out of a cooler; he waved at us with his machete (in a friendly way). The ride wasn’t hard at all — just enough breeze to keep you cool but not so much that your hat flies off.
Halfway through, we parked under some shade and Mark handed out slices of cold Key Lime pie on little paper plates. It tasted tangy and sweet at once — honestly better than any I’ve had before (sorry Mom). There was this moment when everyone went quiet for a second except for the sound of bikes clinking together and some distant rooster crowing. I didn’t expect to feel so relaxed in a group tour setting, but something about sharing pie with strangers under palm leaves just worked. We finished up by looping past Hemingway’s house — Mark had this way of making even old bricks seem interesting.
The tour lasts about two hours from start to finish.
Yes, cold bottled water is included for all riders.
Yes, each participant gets a slice of cold Key Lime pie during the ride.
Yes, all riders receive discounts on future bike rentals and merchandise.
The route is easygoing and suitable for all fitness levels; infant seats are available.
You’ll visit top attractions in Old Town including coastal viewpoints and Hemingway’s house (outside).
Yes, service animals are allowed during the bike tour.
The ride begins in Old Town near both Gulf and Atlantic coasts.
Your day includes use of a comfortable bike with specialized infant seats if needed, guidance from a knowledgeable local who shares stories along every stop, plenty of cold bottled water to keep you refreshed under the sun, plus a generous slice of real Key Lime pie served mid-ride. You’ll also get discounts on future rentals or merch after your trip wraps up back in Old Town.
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