Luis’s Guide to Sunburns, Shipwrecks and Sins That Don’t Count South of Florida City
You don’t “vacation” in the Keys. You cross over. Somewhere around the Last Chance Saloon in Florida City, the laws of physics stop working and time slows down. You start wondering why that pelican is staring at you like you owe it money. And yes, that iguana somehow decided to sleep off its kill of the day on top of your hood… and there’s nothing you can do about it.
In this guide
- Mile Marker Zero – Key West: It’s the end of the road and the start of bad ideas
- Bahia Honda State Park – It’s a postcard with rusty teeth
- Islamorada – It’s where the bar tabs are as tall as the fish tales
- Marathon – The Keys’ witness protection outpost
- Big Pine Key – It’s where the deer look like they’ve been shrunk in the dryer
- The Lower Keys – This is the last stop before pirates and madness
The 106-mile Overseas Highway isn’t just a road, it’s a behavioral filter. It’s a place that slaps constraints and swings you into a Monty Python routine. And you’ll end up loving it. Why? Cause, someone had to explain the American Eagle and Sidney Sweeney scandal. It’s just a commercial, right? What do you mean is so much more? A double what?”
People either emerge on the other side suntanned and blissful or sunburned, broke and missing at least one flip-flop. And it’s not random. The Keys size you up. They decide if you’re a weekender, a lifer or somebody’s third husband who “mysteriously fell off the boat” in ’88.
So, slap on some SPF 90 and keep your bail money in a waterproof pouch. Let’s go.
What to do in The Keys
1. Mile Marker Zero – Key West: It’s the end of the road and the start of bad ideas
Here’s the thing: Duval Street isn’t a street. It’s a living organism that’s still recovering from Woodstock. And once, like Brian Wilson, it did something potent in a pool and suddenly created “Pet Sounds.” It’s still recovering, but folks love it just as it is.
The street is a long, skinny, fermented-scented creature that feeds on tourists and sometimes regurgitates them in front of Sloppy Joe’s at 3 a.m. Hemingway drank here, Mel Fisher found treasure here and Jimmy Buffett turned the whole island into a business plan here.
One night, I saw a bachelorette party start at Irish Kevin’s, detour into a sunset cruise, crash a drag show at Aqua, then end up at Rick’s with one less bridesmaid than they started with. We never found out if she came back.
Must dos:
- Photo op at the Southernmost Point Buoy: Yes, the line’s long. No, you’re not cutting. That sweet little urchin? Just pay him and hope he doesn’t puncture your tires.
- Captain Tony’s Saloon: Once a morgue, now a bar with bras hanging from the ceiling and a tree in the middle. Don’t ask how many of those bras are from tourists who “never came back.” Oh, and the tree? They hanged pirates off that thing. So, haunted as all heck.
- Sunset at Mallory Square: It’s part magic and part grift. Sword swallowers, cats on tightropes, jugglers yelling about tips like they’re calling a hostage negotiation or that scene in “From Dusk Till Dawn with Cheech”… You know the one.
2. Bahia Honda State Park – It’s a postcard with rusty teeth
Bahia Honda is the pretty one. The tropical one. The “Oh my god, I’m in a Corona ad” one. But it’s also got that giant abandoned railroad bridge looming over it… a leftover from Henry Flagler’s grand plan to connect The Keys by rail before a hurricane in ’35 chewed it up like an old toothpick.
Locals use it as a landmark. Fishermen use it as a cover story. (“Honey, I wasn’t drinking at the marina – I was fishing under the bridge.”) And yes, there are sharks… But there are so many other things in the ocean that the “taste test” isn’t really an issue.
Pro tip: Bring your own food unless you enjoy paying $16 for a hot dog that tastes like regret.
3. Islamorada – It’s where the bar tabs are as tall as the fish tales
Islamorada’s the “sport fishing capital of the world,” which is true. But here’s the subtext: It’s also the BS capital of the world. The guy at the bar will tell you about the 700-pound marlin he caught on a Cuban cigar and dental floss, and you’ll nod politely while Googling “biggest marlin ever caught” under the table.
Robbie’s Marina is a must. Pay $5 to feed giant tarpon, then watch as a pelican straight-up mugs you for your bait and teaches you a valuable lesson about Florida wildlife – it has no boundaries.
Do visit:
- Hurricane Memorial
- Florida Keys’ Brewing Company
- Loreleis’ Restaurant
- Whale harbor Seafood Buffet
4. Marathon – The Keys’ witness protection outpost
Marathon’s not flashy. It’s the Keys’ mullet haircut, business in the front (Publix, Home Depot), party in the back (beach bars, questionable motels). It’s where people go when they want to live in the Keys without the “Key West will eat your soul” factor.
Seven Mile Bridge is the star here. The view will make you cry, but so will getting stuck behind a guy in a golf cart doing 15.
Also, the Turtle Hospital. Real turtles and real surgery. And a gift shop that somehow sells stuffed manatees.
Visit:
- The Brass Monkey
- Sombrero Beach
5. Big Pine Key – It’s where the deer look like they’ve been shrunk in the dryer
Key deer: Imagine a Bambi you could fit in a beach tote. They wander into traffic, hang out at Circle K and lick salt from people’s cars. Don’t feed them. You’ll get fined and they still come back.
The legendary No Name Pub is here. Cash-only, covered in dollar bills and once supposedly a brothel. Order the pizza. It’s the only place in Florida where anchovies don’t feel like a hate crime.
6. The Lower Keys – This is the last stop before pirates and madness
Once you pass Big Pine, the chain gets thin. Fewer tourists. More folks who live on houseboats and look like they’ve been through five hurricanes and three elections without voting once.
Looe Key Reef is a bucket list dive spot: clear water, rainbow fish and the occasional curious shark that swims just close enough to remind you where you are on the food chain.
At Boca Chica, behind the Naval Air Station you’ll find: Geiger Beach and a little slice of madness called Red’s Place (a great abandoned beach with history)
Planning a Keys trip? Before you book, skim our worst times to visit Key West so you avoid the wrong week (Fantasy Fest, hurricane season, Lobster Mini-Season). And the what not to do in Key West guide covers the island-specific mistakes that mark you as a tourist. If you’re flying in, the MIA vs FLL breakdown matters — the wrong airport adds real time to the 3-hour Keys drive.
The final Luis sermon
The Keys are a social experiment with 80 proof whatever and a warning label “might induce blindness.”.
All Jimmy Buffett, all Carl Hiaasen, all Tim Dorsey and one part “Dateline” episode.
If you’re not driving back over the Overseas Highway with sand in your shoes, conch fritter crumbs in your lap and a new friend named “Sharky” texting you about a poker game on a boat… you didn’t do it right.
What is the best thing to do in The Keys? Do you agree with our list? Let us know in the comments!