A rooster woke us at 5 AM. Not an alarm that sounds like a rooster—an actual rooster, strutting down the street like he owned the joint. Welcome to Key West, where the chickens have attitude, and nobody’s in much of a hurry to do anything about it.
We’d come down to the southernmost tip of the continental U.S. with vague plans involving sunshine, seafood, and a Jimmy Buffett Margarita. What we got was so much better than we’d expected
Day One: Cats, Buoys, and Sunset Spectacles
Our first stop was the Ernest Hemingway Home and Museum, which sounds very serious and literary until you realize it’s basically a cat sanctuary where a famous writer once lived. About fifty polydactyl cats (cats with six toes) roam the property like they’re the real attraction. And honestly? They are.
Our guide shared stories about Papa Hemingway’s writing routine and wild adventures, but I was mostly watching a gray tabby with six toes lounging on the desk where For Whom the Bell Tolls was written. That cat knew exactly how important he was.
Zach’s pick: The Old Man and the Sea– The story of a down-on-his-luck Cuban fisherman and his supreme ordeal—a relentless, agonizing battle with a giant marlin far out in the Gulf Stream.
Rachael’s pick: Beautiful Exiles – while this book is a historical fiction that focuses on Martha Gellhorn, the majority of the book is set in Key West, with the plot revolving around her relationship with Hemingway.
After the Hemingway House, we made the required pilgrimage to the Southernmost Point. Yes, there’s always a line to get your photo with the big concrete buoy. Yes, it’s touristy. But standing there, knowing Cuba is just 90 miles away, feeling the Atlantic and Gulf waters converge—there’s a thrill to occupying America’s edge.
The afternoon became a blur of wandering Duval Street. We popped into shops selling everything from beautiful handmade jewelry to t-shirts with jokes we can’t repeat here. We stopped for key lime pie, which made us wonder why anyone would bother making any other kind of pie. We eventually landed at a local favorite, Cuban Coffee Queen. Not only is the coffee excellent, but the food offers delicious gluten-free options.
With the sun going down,, we headed to Mallory Square for the nightly sunset celebration. This isn’t just people watching the sun go down—it’s a full street festival. Jugglers, acrobats, musicians, and fortune tellers all perform as the sky transforms through shades of orange, pink, and purple. Strangers become friends as everyone turns westward, collectively exhaling as the sun melts into the horizon.
Day Two: Choose Your Own Adventure
We woke up with ambitious plans and immediately split into two camps based on our answer to one question: fish or bike?
Half our crew headed out fishing and caught grouper, mangrove snapper, and even a shark! Sea turtles popped their heads up in greetings as the boat explored the surrounding keys. They returned hours later with sun-drunk grins, wild fish tales, and enough fresh catch for dinner.
We used ShadowCaster Fishing Charters and we were beyond happy with the experience! The boat was nice and plenty capable for the flats and shallow fishing we did. The guide was experienced and knowledgeable about the fish and the area. We caught hundreds of fish between the four of us and enjoyed a beautiful day on the water!
The rest of us opted for e-bikes, which might be the best way to explore Key West without actually breaking a sweat in the Florida heat. We cruised through Old Town’s quieter streets, past conch houses painted in colors like “sunset orange” and “I’m-on-vacation pink,” before landing at the Key West Tropical Forest & Botanical Garden.
Our bike rental company was We Cycle Key West, and the experience was excellent! For an affordable price, the company dropped off and picked up our bikes at the marina, and we were able to enjoy a day on two wheels.
The Key West Tropical Forest and Botanical Garden was a surprise gem—a peaceful oasis full of butterflies, native plants, and absolutely zero cruise ship crowds. We wandered the trails, learned about hardwood hammocks (which sounds made up but isn’t), and enjoyed being the only people there who weren’t birds.
Both groups reconvened that evening with the same conclusion: we’d picked the right activities.
No trip to Key West is complete without a stop at El Siboney. When you plug the address into your GPS it looks like you’re headed into a residential part of the island and you are. This restaurant is surrounded by homes and a little off the beaten path. The classic Cuban food is full of flavor and the sweet plantains are the best!
Day Three: Dry Tortugas—Worth the Early Alarm
Getting to Dry Tortugas National Park requires a 5:30 AM wake-up call and a two-hour ferry ride. We made another stop at Cuban Coffee Queen, where we knew the brew was strong enough to keep us awake.
Seventy miles west of Key West, this remote cluster of islands centers around Fort Jefferson, a massive hexagonal fort that rises from the sea like something from a fever dream. The two-hour catamaran journey is quite the ride. Stand at the front of the ferry to get the wind in your face and see if you can spot marine life on the horizon. The tour guide provided historical information about the island and tips for making the most of the day.
Dry Tortugas isn’t just about the impressive Civil War-era fort. The snorkeling here is amazing. The water around Dry Tortugas is ridiculously clear. We slipped on our snorkel gear and found ourselves swimming with sea turtles, gliding past coral gardens, and trying to identify tropical fish we’d only seen in screensavers. It’s the kind of snorkeling where you keep lifting your head up to make sure you’re still on Earth.
There are many options for traveling to Dry Tortugas, but the most cost-efficient, by far, is by taking the Yankee Freedom Ferry. While the ferry is still expensive (around $250 USD/person), it is the cheapest and most comprehensive offering for visiting the island. Breakfast and lunch are included in the voyage, as is all of the snorkeling equipment you might need to swim around the island. Visiting Dry Tortugas was the focus of our trip and we were so glad that we chose to take the ferry out to the fort.
The ferry ride back felt too short. We’d spent the day seventy miles from civilization, and returning to Key West almost felt like culture shock.
The night ended with dinner at Hogfish Bar & Grill. Located on Stock Island, it’s a must-stop for delicious food. The waitress was incredibly knowledgeable about food allergies and they had plenty of gluten-free options.
Day Four: Bahia Honda State of Mind
If Dry Tortugas was about adventure, Bahia Honda State Park was about doing absolutely nothing and doing it exceptionally well.
About 35 miles up the Keys from Key West, Bahia Honda has some of the best natural beaches in Florida—powdery white sand, water in every shade of blue, and enough space that you don’t feel like you’re at a crowded pool party. We unfortunately hit the park on a very windy day, so we spent most of our time hiking along the beach and exploring the hiking trail that takes you to the historic Old Bahia Honda Rail Bridge, a remnant of Henry Flagler’s Overseas Railroad, built in 1912 and later converted for auto use before closing in 1972. The birds-eye view of the park is worth the trek up the bridge. On any other day, we recommend claiming your spot, setting up camp, and swimming, floating, and napping in rotation.
The Farewell
Our last night in Key West, we sat on the deck of our rented sailboat as the sky darkened and the roosters finally quieted.
Our lodging in Key West was aboard a 40′ Beneteau mono-hull sailboat courtesy of SeaStaysKW. Our boat was moored in the Perry Marina, and the stay was excellent. The boat is comfortable, if not a little tight for 3 couples. All of the amenities are available between the boat and the marina. Our host, Dee, was wildly helpful and responsive. We would stay with SeaStaysKW again without hesitation.
Key West has this way of making you forget about schedules. Maybe it’s the island geography—you’re literally as far as you can go and still be in the continental U.S. Maybe it’s the motto: “One Human Family.” Or maybe it’s just that roosters don’t care what time your meeting is, and the cats definitely don’t. We came for sunshine and margaritas. We left with stories about six-toed cats, snorkeling, and the best key lime pie we’ve ever tasted. We also left completely understanding why people move here and never leave.
Key West doesn’t give you a vacation. It gives you a different pace, a better sunset, and permission to let the roosters set your schedule.
Ready to plan your own Key West escape?
Download our detailed 4-day itinerary with timing, insider tips, restaurant recommendations, and everything we learned along the way. Get your free guide and start planning your island adventure today.
