Miami To Key West Road Trip: Things To Do Along The Way

Key West Road Trip

Road Trip to Key West

Key West, Florida

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.

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!

I spent 4 days exploring the Florida Keys with my friends Steph & Lauren. These were our favorite things to do on a road trip from Miami to Key West.

Key West Road Trip

Rocking the Drop Top Jeep

Key West Road Trip

Driving Down from Miami

Rent A Jeep In Miami

The best way to experience the scenic Florida Keys is behind the wheel of a convertible, like the fun Jeep Wrangler we rented with Tons Of Fun Tours.

They make it easy by delivering it to the airport or your hotel in Miami. Once you have it, just drop the top, remove some clothing, turn up the volume, and enjoy the drive!

We made our way down to Marathon Key under the warm sun stopping for photos and quirky souvenirs, like a stuffed shark who would become our mascot for the rest of the trip.

Key West Road Trip

Feeding Tarpon at Robbie’s

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.

Key West Road Trip

Faro Blanco Resort

Key West Road Trip

Fish Sandwich at Tarpon Creek Bar & Grill

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.

While in Marathon, make sure to grab some lunch at Tarpon Creek Bar & Grill and dinner at the Lighthouse Grill. Both serve up all kinds of tasty fresh fish caught locally.

Key West Road Trip

Old Railroad Bridge

Key West Road Trip

Seven Mile Bridge

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.

Key West Road Trip

Fort Zachary State Park

Key West Road Trip

Sailing in Key West

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.

Go Snorkeling

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.

Hemingway 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).

Key West Road Trip

Key West Sunset

Key West Southernmost Point

Southernmost Point

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.

Southernmost Point Buoy

You can’t visit Key West and not stop by the 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 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!

Key West Road Trip

Key West Marriott Beachside

Where To Stay In Key West

While we were in Key West, we stayed at the Key West Marriott Beachside. The suite included a kitchen, which was great for preparing a late-night snack after coming home from the bars on Duval Street.

For other options, here are my recommendations:

Hostels In Key West

Seashell International Hostel – Excellent central location, but a bit cramped. Not many options for backpackers though!

Hotels In Key West

Key West Marriott Beachside – Waterfront location, super nice, full suites with kitchens available.

Courtney Place Historic Cottages – Charming, comfortable, and close to everything. Very friendly staff.

COUPON CODE! For a special $30 off your next hotel stay over $60, make sure to use my special link.
Key West Food

Fresh Caught Hogfish at Bagatelle Restaurant

What 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!

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! ★

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.

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More Information

Location: Key West, Florida
Accommodation: Key West Marriott Beachside
Useful Notes: The drive from Miami to Key West takes about 4 hours without stopping, but you’ll want to plan for many stops. You’ll get the best weather during winter high season. Summer can be humid and rainy with the occasional hurricane.
Recommended Guidebook: Lonely Planet Miami & The Keys
Suggested Reading: Key West: A Quirky Slice Of America


Fantasy Fest In Key West
Learning To Sail In Key West

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This is a post from The Expert Vagabond adventure blog.