You’re standing at the tip of the United States. It's hot. The air in Key West tastes like salt and overpriced lime juice, and you’ve got to get to Miami. Most people—honestly, probably 90% of the tourists you see wearing "Conch Republic" t-shirts—will tell you to just drive the Overseas Highway. They’ll talk about the Seven Mile Bridge and the turquoise water. They aren't wrong; it’s beautiful. But if you’ve ever been stuck behind a slow-moving RV on a two-lane road with no passing zone for forty miles, you know the dark side of that drive.
Taking a flight Key West Miami is the travel hack that feels like a luxury but often ends up being a logistical necessity.
It’s a 160-mile trip. In a car, that’s three and a half hours if the gods of traffic smile upon you. If there’s an accident on US-1? Forget it. You’re looking at six hours of staring at the bumper of a Ford F-150. In a plane, you’re in the air for maybe thirty-five minutes. Sometimes less. By the time the flight attendant finishes the safety demo and the pilot levels off at a low cruising altitude, you're already seeing the high-rises of Brickell poking through the clouds.
The Reality of the Key West to Miami Route
American Airlines and Silver Airways basically own this sky. American Eagle—usually operated by Envoy or Republic—runs Embraer 175s or similar regional jets. These aren't the tiny, vibrating "puddle jumpers" people are often scared of. They’re real planes with real overhead bins. Silver Airways is a different beast. They use ATR turboprops.
If you haven't flown a turboprop lately, it’s a vibe. It’s louder. You feel the air more. But the views? Unmatched. Because these planes fly lower than the massive transcontinental jets, a flight Key West Miami becomes a low-altitude sightseeing tour. You can see the reef. You can see the distinct line where the shallow Gulf water meets the deep Atlantic blue.
Prices fluctuate wildly. I’ve seen seats for $99, and I’ve seen them for $450 because a cruise ship just docked and 3,000 people are trying to get to Miami International (MIA) at the same time.
Why not just take the bus?
Sure, the Greyhound or the "Keys Shuttle" exists. They’re cheaper. But they’re subject to the same soul-crushing traffic as a rental car. If you have a connecting flight in Miami heading to London, New York, or LA, the bus is a gamble I wouldn’t take. Missing a $1,200 international connection because a boat hit a bridge pylon in Islamorada is a bad way to end a vacation.
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Navigating Key West International (EYW)
Key West International Airport is tiny. It’s charming in that "we don't have enough gates so you're walking on the tarmac" kind of way. Lately, they’ve been doing massive renovations—the Concourse A expansion—to modernize the place. It needed it. For a long time, the departure lounge felt like a high school cafeteria that sold expensive rum cake.
Even with the upgrades, EYW is efficient. You can usually show up an hour before your flight and be totally fine. Try doing that at MIA or FBO.
The runway is short. 5,076 feet, to be exact. This matters because it limits the size of the aircraft that can land. You won't see a Boeing 777 here. Because of the short strip, pilots have to "plant" the plane. Don't be alarmed if the landing feels a bit firm. They’re slamming the brakes and hitting the thrust reversers because they don't have miles of asphalt to play with. It’s a professional maneuver, not a bad pilot.
What Most People Get Wrong About the Cost
People look at a $200 ticket and scoff. "I'll just rent a car for $80," they say.
Let's do the math.
One-way rental car drop-off fees in Florida are notorious. You pick up in Key West and drop at Miami International? The rental company might slap a $100 to $150 "convenience" fee on that. Add the gas. Add the $25 for a mediocre lunch in Marathon because you got hungry halfway through. Add the four hours of your life you’ll never get back.
Suddenly, that flight Key West Miami looks like a bargain.
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Especially if you are a frequent flier. American Airlines treats this as a standard segment. If you’re hunting for status, these short hops are gold. You get the same segment credit for a 30-minute flight as you do for a five-hour slog to Seattle.
The "Secret" Alternative: Seaplanes
If you want to talk about the real Way-to-Go, it’s Key West Seaplane Adventures, though they mostly focus on the Dry Tortugas. However, private charters do run between Miami’s seaplane base (near the cruise terminals) and the Keys. It’s prohibitively expensive for most, but if you want to skip the airport security lines entirely and land right in the water, it’s an option that exists in the realm of high-end travel.
For the rest of us, it’s the Silver Airways ATR or the American Eagle jet.
Timing Your Booking
Key West is seasonal. Deeply seasonal.
If you’re trying to fly during Fantasy Fest (late October) or over New Year’s, you better book six months out. The island fills up, and the planes follow suit.
Mid-week flights are usually the sweet spot. Tuesday and Wednesday flights between EYW and MIA can be surprisingly empty. I’ve been on flights where there were more crew members than passengers. It feels like a private jet for the price of a pair of sneakers.
The Weather Factor
This is the Caribbean-adjacent tropics. Thunderstorms happen every afternoon in the summer.
A flight Key West Miami is often delayed by 45 minutes because a massive cell is sitting right over the Everglades. The good news? These storms move fast. Usually, you’ll sit at the gate, the pilot will come on the intercom and tell you about the "weather window," and 20 minutes later, you’re in the air.
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Don't panic if your flight shows a delay. It’s just life in South Florida.
Arrival at MIA
When you land in Miami, you’ll likely arrive at the North Terminal (Concourse D). This is American’s massive hub. If you’re connecting, it’s a breeze. If Miami is your final destination, be prepared for a walk. MIA is huge. It is the literal opposite of the airport you just left.
The Skytrain in Concourse D is your friend. Use it. Your legs will thank you.
Actionable Steps for Your Trip
To make the most of this route, stop thinking like a budget traveler and start thinking like a strategist.
- Check the One-Way Rental Math: Before booking, go to a site like Hertz or Enterprise. Check the price of a one-way rental from EYW to MIA. If it’s over $150, just book the flight.
- Download the Airline App: In Key West, gate changes happen because there are so few gates. The app will tell you the change before the gate agent even picks up the microphone.
- Pick the Right Side of the Plane: Flying north from Key West to Miami, sit on the right side (Seat F on most regional jets). You’ll have a better view of the islands and the reef as you climb out.
- Mind the Luggage: Silver Airways and regional partners have strict weight limits. If you’re carrying a 60-pound suitcase full of seashells and rum, you’re going to pay. Keep it under 50 pounds to avoid the heavy-bag sting.
- Use the MIA Mover: If you’re heading to South Beach or Downtown Miami after landing, don't take an expensive Uber from the terminal. Take the MIA Mover (the free train) to the Miami Intermodal Center. From there, Ubers are cheaper, and the "Beach Express" bus is only a couple of bucks.
Flying this route isn't about being lazy. It’s about valuing your time in a place where "island time" can quickly turn into "stuck in traffic time." If you have the choice, take the sky. The view of the turquoise water from 10,000 feet is a much better way to say goodbye to the Keys than looking at a billboard for a personal injury lawyer on the side of the highway.