Florida Keys: The Ultimate Road Trip

Here’s how to make the most out of your road trip to the Florida Keys.

“It’s a different world down here,” said Justin, a tile guy who sat next to me at a Doc’s Diner in Key Largo. “I don’t understand people who wake up and say F**k. I want to live the dream. I moved here two years ago and never looked back, why would I?”

He was from Kansas. I bought his breakfast.

I was on a mission to have a good time post pandemic. A road trip to the Florida Keys was the easy answer with her sunshiny skies, salty breezes and good food that wasn’t curbside pickup.

You see, this trip crosses 44 islands, 42 bridges and is 113 miles long. It starts near Miami and ends in notorious Key West. It needs to be done with windows down and reggae music blaring for the full effect. Besides, this is one road trip you’ll want to take slowly.

Let yourself feel “island time”. And by slow, I mean, stop everywhere along the way to get the full experience.

Plus, you have to go slow, speed traps are everywhere on the Overseas Highway.

Thinking about what Justin (at the diner) said about it being a different world here, is something you have to see to get it. -Because, once you hit the first Key, you begin to recognize a difference. It’s almost like you’ve left Florida for a Caribbean island.

As soon as you feel the feels of driving down a skinny road surrounded by water on both sides, passing endless marinas and nautical shops, don’t be surprised if you start humming Jimmy Buffet songs and craving a margarita!

Keep your eyes out for dolphin and flamingo mailboxes along the way too.

Tips to plan your Florida Keys road trip:

When: Anytime really. The keys are one of the sunniest places in the US. The best time may be from March to May after the big tourist season. If hurricanes worry you, avoid August and September too.

How Long: Ideally you’ll want at least a week to see and do it all. Or be like Justin and never leave.

Where to stay: for the full experience stay a few nights in the upper Keys like Islamorada, a few nights in the middle Keys like Marathon and top it off with a few nights in Key West.

Check here for hotel options.

Good to know: The Overseas Highway is measured in mile markers (MM) and ends in Key West at MM0. Key Largo is MM102, Marathon is MM60. The locals speak in mile markers when giving directions.

Pro Tip: Do try all the versions of Key Lime Pie. You decide if you like the meringue vs whipped cream versions. It’s a local tradition.

All The Best Stops Along The Way to Key West:

Homestead

‘Robert is Here Fruit Stand. Get your first taste of Florida’s kitschy-kooky at this family run produce market that’s anything but typical. Part market, part zoo, you never know what shows up here. Do try an exotic fruit milkshake and stock up on road snacks at this fun stop

Key Largo

John Pennekamp State Park | Key West Fisheries |Alabama Jacks

Islamorada

Rain Barrel Village | Robbie’s | Postcard Inn | Florida Keys Discovery Center

This area was the Filming location used in the popular Netflix series Bloodline

Marathon

Turtle Hospital | Theater of the Sea

7 Mile Bridge

Sunset Grill | Bahia Honda State Park

Key West

Trolly Tours |Mallory Square | Hemmingway House |Smathers Beach |Southernmost Point

Everywhere you stop has surprises in store. Go explore, you can’t get lost.

Oh, and consider renting a convertible.

Are you ready for a Real Florida Adventure?

Contact us and we’ll share inside scoop you won’t find online.