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Key West, Florida [UPDATED: January 2019]
Driving down through the beautiful Florida Keys from Miami to Key West is a classic American road trip. Here’s what you can expect on the journey, plus my favorite things to do!
Key West is the Southernmost city in the United States, just a 4-hour drive from Miami on the scenic coastal Overseas Highway with plenty of interesting (and kitschy) things to do during the 110-mile trip, including crossing 42 different bridges.
No visit to South Florida is complete without road tripping down to the Conch Republic for a few days. Especially if you like pirates, key lime pie, water-sports, and live music!
These were our favorite things to do while driving from Miami to Key West!
Rent A Car From Miami
The only way to experience the scenic Florida Keys is behind the wheel of a convertible Jeep Wrangler like the one we rented from Tons Of Fun Tours in Miami.
Drop the top, and enjoy a beautiful coastal drive down to Key West!
To start our adventure, we slowly made our way to Marathon Key under the warm sun with the soft-top down.
Stopping for photos and quirky souvenirs, like a stuffed shark who would become our mascot for the rest of our Key West road trip!
Feeding Wild Tarpon
Dangling my arm over the water, a massive sea creature suddenly leaped out and wrapped its mouth around my hand to the horror of screaming onlookers.
Growing up to 8 feet long and weighing over 200 pounds, Tarpon is huge game fish that live in the tropical waters off the Florida Keys.
Fishermen from around the world travel here just for a chance to catch (and release) one of these monsters.
However, you can also buy a bucket of bait and hand-feed these giant fish from the docks of Robbie’s Restaurant on Islamorada. Be careful, they have small teeth that will leave marks!
It’s a must-do experience for any road trip from Miami down to Key West.
Exploring Marathon Key
While you could drive directly from Miami to Key West in about 4 hours, there’s a lot of cool stuff to see around the rest of the Florida Keys too.
I recommend driving down over the course of 2 days, spending a night in Marathon before continuing on to Key West.
That’s exactly what we did, booking a room at the beautiful Faro Blanco Resort to break up the drive.
Walk Seven Mile Bridge
Driving over the vibrant blue ocean for miles on a bridge that never seems to end was one of my favorite parts of road tripping the Florida Keys.
The Seven Mile Bridge was originally constructed in 1912 for railroad traffic.
These days you drive across it on your way to Key West, or park just north of the bridge at Mile Marker 47 in Marathon and go walking or biking over to Pigeon Key along the older span.
Things To Do In Key West
Learn To Sail
Gather a few friends and charter a boat for sailing lessons with Sunset Sail Key West like we did. Explore the islands powered only by the wind. They offer day trips, sunset sails, and overnight excursions.
Dive into the ocean and swim with sea turtles, nurse sharks, parrot fish, and spiny lobsters on the shallow reefs around Key West. Join a boat tour or snorkel from the beach at Fort Zachary Taylor State Park.
Visit Hemingway’s House Cats
Ernest Hemingway lived in Key West during the 1920’s, and you can visit his old house, and make friends with the 50 or so six-toed cats that live there. Perfect for crazy cat lovers (like me).
Watch Key West Sunsets
The sunsets in Key West are some of the best I’ve ever seen. Grab a beer and watch in awe from Mallory Square as the sun drops below the Gulf of Mexico, painting the sky in brilliant shades of pink, purple, yellow, and orange.
Reach The Southernmost Point Buoy
You can’t visit Key West and not stop by the southernmost point in the continental United States, which is marked by a red & white concrete pillar. The line for photos is long unless you get there early in the morning!
Bar Hopping On Duval Street
Duval Street may only be a mile long, but it’s packed with small bars & old Victorian mansions. Pop in and listen to one of the many live bands playing Jazz, Cuban, or Salsa music. Don’t miss the Green Parrot Bar or the (clothing optional) Garden of Eden!
Where To Stay In Key West
My suggestions for places to stay during your road trip from Miami to Key West:
IN KEY WEST:
Where To Eat In Key West
One of the best meals I ate in Key West was at Bagatelle Restaurant, located in a beautiful old building on Duval. Locally caught Hogfish with jasmine rice and pineapple salsa. Yum!
The key lime pie was born in Key West during the early 20th century. It’s made using the small key limes native to the area, more flavorful than regular limes. The Key Lime Pie Company makes a good one!
Key West Travel Tips & Advice
- The drive from Miami to Key West takes about 4 hours without stopping, however, with all the fun stops, expect a full day.
- Winter is a great time to visit Key West, but it’s also the busiest due to high-season. Instead, the shoulder seasons of March – May is less packed, hotel rates become reasonable, and the weather is similar.
Traveling To Key West Soon?
Don’t forget travel insurance! I’m a big fan of World Nomads for short-term trips. Protect yourself from possible injury & theft abroad. Read more about why you should always carry travel insurance here. ★
Bonus Travel Video! Miami To Key West Road Trip
(Click to watch Miami To Key West Road Trip on YouTube)
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Have any questions about Key West? What about other suggestions? Drop me a message in the comments below!