The Ultimate Florida Keys Road Trip

Your Road Trip Story Starts Here

“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 and say %&$# every day. I want to live the dream so I moved here two years ago and never look back, why would I?”

He was from Kansas. I bought his breakfast

All The Best Stops Along The Way

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; is 113 miles long starting 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 slow. C’mon, it’s island time. And by slow, I mean, stop everywhere along the way for the full experience.

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

Key West bound

Thinking about what Justin (at the diner) said about it being a different world down here is something you have to see with your eyes to really get it. Because once you hit the first key, it starts to feel like you’re in the American Caribbean, a technically nonexistent place. As soon as you feel the feels of driving down a skinny road surrounded by water on both sides, passing mailboxes shaped like fish, endless marinas and nautical shops, I bet you’ll start humming Jimmy Buffet songs.

Keep your eyes out for pink
flamingo mailboxes

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.

Insider Tip: Must try all the versions of Key Lime Pie, then decide if you like the meringue vs whipped cream versions.

Fun Ideas for Best Stops Along The Way to Key West:


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


Rain Barrel Village | Robbie’s | Holiday Isle Tiki Bar | Postcard Inn |Filming location for popular Netflix series Bloodline


Turtle Hospital | Theater of the Sea

7 Mile Bridge

Sunset Grill | Bahia Honda State Park

Key West

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

Are you ready for a Real Florida Adventure?

By no means is this all there is, everywhere you stop has surprises in store. Go explore, you can’t get lost. Oh, and consider renting a convertible.

Wondering the best places to stay? Contact us and we’ll share the scoop.

Ask a local their favorite restaurant and
they’ll respond with a mile marker