A Miamian’s take on the best ways to get to Key West
The weather in Florida is unstable. I mean regular bouts of guano-like insanity. It’s not just the climate, it’s everything. Most of all, the behavioral forecast for South Florida, a place where logic melts faster than ice being swirled around by the Devil on his throne.
Down here, everything eventually becomes unglued. Gravity is optional. Cause and effect are ignored. And, the last guard rails of what little there is of logic, are swept out to the sea once you hit the Florida Keys.
The Islands of the Florida Keys
Each island is its own microcosm of behavioral anomalies. Some homes are owned by small oil emirates. Others are rented out to vape-heavy tourists from Reno. But some smack between predator hide outs and family-run fish shacks that still barter in grouper and wet t-shirt contests.
We also have retirees that bought in before a shack was worth more than the Hope diamond. There are fishermen that decided to set up shop on No Name Key and go off-grid. We have small deer and smuggler dens. There is also a Navy Station in Boca Chica, and a CIA substation with radar pointed at Cuba.
The Keys are a stew: cooked in narco money laundering schemes, CIA real estate boondoggles and Jimmy Buffett’s sweaty, sandal-clad ghost. Because here, law and order are mostly metaphors, and retirement is a martial art. So don’t show up thinking it’s just a beach-and-beer fantasy.
The glue: Highway 1
And the glue holding this wonky archipelago together? U.S. Highway 1. A ribbon of scenic wonder that is, most of the time, a soul-flattening parade of rental cars and RVs all vying for position, disregarding the speed-limit and hoping the whole thing won’t come to a grinding halt because some wayward iguana crossed the road.
In this article, we’re giving you the 411 on how to get to the Keys. Highways, boats, planes, buses, possibly astral projection. Whether you want to lean into the experience or wallow in it like an air-conditioned fever dream, we’ve got your plan. Or at least a few options that don’t involve getting stuck behind a man towing a jet ski at 35 mph for the next seven hours.
Let’s get into the wanton havoc that is traveling to the southernmost corner of the continental U.S. where it all unravels in the best possible way.
Getting to Key West: Pick Your poison
By car: The road trip to the edge of the Earth
Let’s get something out of the way: U.S. Highway 1 is a test of character. It’s also the only road in and out. Therefore, you treat it as a necessary evil and enjoy the views – or let it eat you whole.
The 113-mile drive from Miami to Key West is one rolling screen saver. But it also has ONE lane in each direction. No passing. Occasional iguana crossings. And a man towing three kayaks with a Corolla doing 40 mph for an eternity.
And, given that the Overseas Highway passes through some National Preserves – with actual miniature deer crossings – some stretches have speed limits that might get a pedaling cyclist a ticket.
But then there’s Seven Mile Bridge. That stretch though? It is cinematic. That’s where you roll the windows down and pretend you’re being hunted by Cuban smugglers in a Tarantino film. Off to the side? That’s Pigeon Key, a tiny island once home to Henry Flagler’s railroad workers, now haunted by the ghosts and wedding planners.
Also, keep an eye out for the Key deer. They’re adorable and also protected. And if you believe the rumors, they run a loose criminal syndicate on Big Pine Key.
By bus: The Greyhound of the damned (or not)
You can take a bus from Miami to Key West. But understand this: you’re not just boarding a bus. You’re boarding a moving confessional booth.
It’s part tropical pilgrimage, part overheated therapy session. You’ll meet a woman who speaks only in tarot metaphors. And a man hauling a bucket full of ’emotional support shrimp.’ Or possibly a retired Elvis impersonator moving down after his fifth divorce.
FlixBus and Greyhound both run routes. They’re affordable and reliable-ish. They’re the slowest way to unravel your sense of time. But hey, if you’re not in a rush, you’ll see things. If not strange things.
By boat: It’s the high seas and higher chaos
There are charters and captains. There are sketchy dudes named “Captain Steve” with bleached eyebrows and suspicious passports. And then there are the brave few who say: “Let’s sail to Key West.”
Look, if you have access to a boat and someone who knows how to not hit Cuba by accident, go for it. It’s beautiful. Mangroves. Open water. Keys sliding by like a slow striptease.
But it’s also unpredictable. The Gulf Stream is a mood. Storms come in like arguments in a bad marriage: fast, loud, and full of damning callbacks to when the relationship started 40 years ago.
And remember: the smuggler routes from the 80s are still there and some are active. Some say you can anchor at certain coves and hear whispers in the wind: “Don’t touch the crate, Randy.”
By ferry: The chillest way to roll the dice
There is, blessedly, a ferry from Fort Myers to Key West. It’s called the Key West Express, and it’s the smoothest way to get there that still feels a bit pirate-adjacent.
It’s a catamaran with libations, AC, snacks, and about 200 other people wondering if they should’ve just stayed in Naples. The ride takes about 3.5 hours, give or take.
The best part? You arrive in Key West at the harbor with a sunburn and zero traffic trauma. The worst part? If it rains, you will discover what it feels like to be slapped by wet wind at 40 knots.
By flight: fast, brutal, beautiful
You can fly directly into Key West International Airport (EYW) from places like Miami, Tampa, and Orlando. It’s quick and clean. But it’s also the size of a Starbucks bathroom.
The descent into Key West is all thrill ride. It’s the sort of drop down only trained pilots in black-ops who have XP with jungle LZ in midnight drenched Honduras can perform. You’ll come in low over the ocean and wonder if you’re landing on water. And you will clutch the armrest while a baby three rows up lights a cigarette out of stress.
But the view? Ocean on all sides. Turquoise like a tanker of Gatorade just spilled all its lot in the coast.
Choose Your own misadventure
There are ways to get to the Keys that shouldn’t work – but somehow do.
For instance, you could hitchhike. You could fake a mechanical problem on a jet ski and “drift south.” Or you could “borrow” a kayak from a friend in Cutler Bay and paddle until the hallucinations start to make navigational sense.
You could take a seaplane from a guy who insists his name is “Biscayne Dave” and operates out of a shed with no FAA certification but a glowing Yelp review written by someone named “KeyDeer69.”
I once heard of a man who ran his way across the entire highway median, powered solely by passion, pickle banana juice and the fact that he didn’t realize “Forrest Gump” wasn’t a documentary.
Point is: there’s no wrong way, just Florida-shaped ways.
Wait, what about trains?
Ah, yes. The ghost of Henry Flagler just rolled over in his limestone sarcophagus.
There used to be a train. The Overseas Railroad, built by madmen, fueled by passion plays, and held together with engineering duct tape and manifest destiny. It connected mainland Florida to Key West by rail, a miracle of steel over sea.
Until 1935, when a hurricane came through and said: “Nah.” The tracks were destroyed and the dream died. What’s left is the road you drive today – U.S. 1, built over the ghosts of railmen and dreams too humid to last. You can actually see part of it as you zoom by the highway.
So, you can’t take a train anymore. But if you walk Seven Mile Bridge at sunset, and the wind hits just right, you might hear it.
Last stop: no wrong turns, only weird ones
Getting to Key West is never just travel—it’s a rite of passage in Florida.
No matter how you arrive, you’ll end up there blinking in the sunlight, wondering why the sky feels so close, and why a parrot just stole your sandwich while a man in a Speedo tells you he knew Hemingway’s dentist.
So… how are you getting there? Key West doesn’t care — Just show up weird.
Have you traveled to the Keys? What is your favorite way to get there? Let us know in the comments!