9 to 5 Key West: Squeeze in the Best Before Happy Hour
Key West—the land of sunsets, roaming chickens, and more bars per square foot than you ever thought possible. It’s a place where cats have extra toes, Hemingway’s spirit lingers, and key lime pie is practically a religion. If you’ve only got one day to soak in the funky, sun-drenched magic of this island, don’t worry—we’ve got you covered.
This whirlwind itinerary is perfect for cruise ship passengers, day-trippers, or anyone looking to get a taste (literally and figuratively) of Key West before deciding whether to return for a longer stay. Let’s jump in and see just how much island flavor you can cram into eight hours!
9:00 AM – Arrival & The Key to Key West: A Golf Cart
As soon as you step off your cruise ship, you’ll want to get moving. And what better way to zip around this quirky little island than in a golf cart? We rented one from Key West Golf Cart Rentals for $155 for 8 hours. Pricey? Maybe. Worth it? Absolutely.
Key West’s streets are slow-paced, so you won’t feel bad about puttering around town in your little electric chariot. Just be warned—parking is more challenging than finding an actual local in Key West (most residents are either snowbirds or bartenders). Many spots require a permit, and when you do find parking, you’ll probably have to pay for it. But hey, that’s part of the adventure, right?
9:30 AM – The Southernmost Point (That's Not Actually the Southernmost Point)
Next stop: the Southernmost Point Buoy, a massive concrete marker that tells you in big, bold letters that you are, in fact, only 90 miles from Cuba. Fun fact: This isn’t even the true southernmost point—that honor goes to a spot on U.S. Navy property that civilians can’t access. But let’s not ruin the magic!
Expect a line, because everyone and their grandma wants a photo here. The line moves fast, though, so snap your iconic Key West pic and be careful of sea spray—one rogue wave and you might look like you just swam from Havana.
10:00 AM – Hemingway's House: Six-Toed Cats & Literary Legends
Just a short ride away is the Ernest Hemingway Home & Museum. Whether you love Hemingway’s books or just appreciate a man who could drink like a fish and still write bestsellers, this place is a must-visit.
The house itself is stunning, but let’s be real—the main attraction? The six-toed cats. These furry residents are descendants of Hemingway’s own polydactyl cat, Snow White, and they now rule the property. It’s their world; we’re just visiting.
Admission is $18 per person, and you can either take a guided tour or roam around solo. Either way, you’ll leave with a new appreciation for the man, the myth, and the many, many cats.
11:00 AM – Key West Lighthouse: Climbing for the Best View
Directly across from Hemingway’s house is the Key West Lighthouse, one of the island’s most historic landmarks. Originally built in 1848, this lighthouse has seen hurricanes, wars, and more tourist selfies than we can count.
For $15.50, you can climb the 88 steps to the top. It’s a short but steep climb, and your reward is a 360-degree panoramic view of Key West. Plus, it’s a great way to burn off a few key lime pie calories in advance.
Fun fact: One of the lighthouse’s longest-serving keepers was a woman, Barbara Mabredy, who took over in the 1830s when her husband passed away. She ran the show for over 30 years, proving once again that Key West has always been home to some seriously tough (and awesome) people.
12:00 PM – Lunch at Blue Heaven: Chickens, Cheeseburgers, and Key Lime Pie
By now, you’ve probably worked up an appetite, and there’s no better place for a quintessential Key West lunch than Blue Heaven. This place is famous for three things:
- Outdoor seating with live music
- Free-range chickens that casually strut around like they own the joint
- The best Key Lime Pie in town (or so they claim—every place in Key West claims this)
We ordered a blackened mahi-mahi sandwich and a burger, both of which were solid but not life-changing. The real star? The Key Lime Pie. This beauty comes topped with a mountain of meringue, and it’s worth every bite.
If you only eat one thing in Key West, make it this pie.
1:30 PM – Fort Zachary Taylor: History Meets the Beach
Up next: Fort Zachary Taylor State Park, home to both Civil War-era history and one of Key West’s best beaches.
The fort itself, built in 1845, is a fascinating piece of history, and it boasts the largest collection of seacoast cannons in the U.S. But let’s be real—most people come here for the beach.
Surprisingly, Key West isn’t really known for beaches, but this spot is an exception. With clear blue water, soft sand, and plenty of shady spots under pine trees, it’s the perfect place for a quick dip before moving on.
3:00 PM – Mile Marker Zero: The End of the Road
After cooling off, we hopped back in our golf cart and headed to Mile Marker Zero, the official end of U.S. Highway 1. This road stretches all the way from Fort Kent, Maine to Key West—a whopping 2,369 miles.
It’s just a street sign, but hey, it’s a cool street sign.
3:30 PM – Mallory Square: Prepping for Sunset Magic
No visit to Key West is complete without checking out Mallory Square, where the island’s famous sunset celebration takes place every evening.
We were a little early for the party, but at night, this place comes alive with jugglers, musicians, magicians, and food carts. If you have time, stick around—it’s one of Key West’s most legendary traditions.
4:00 PM – Duval Street: Bars, Bars, and More Bars
As our day wound down, we made our final stop at Duval Street, the beating heart of Key West’s nightlife scene. This mile-long strip is packed with legendary watering holes, tourist shops, and live music joints.
We popped into Captain Tony’s Saloon, which claims to be the oldest bar in Florida. The walls are covered in dollar bills and bras, and the barstools have names of famous people who once drank there. Turns out, I was sitting in Jerry Seinfeld’s seat. No pressure.
5:00 PM – Back to the Ship (For Now)
With our time in Key West running out, we returned the golf cart, made our way back to the pier, and waved goodbye—for now. There’s so much more to see in Key West, but for an eight-hour visit, we managed to pack in a whole lot of fun, history, and pie.
Would we come back? Absolutely. Next time, we’ll stay longer, drink more rum, and maybe even join the sunset celebration. Until then, Key West, stay weird.
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