Island Magic: From Key Largo to Key West

In partnership with

A Letter from the Overseas Highway

I’ve made this drive more times than I can count.
But the first time I flew into Miami, rented a car, and headed south? That wasn’t just a drive—it was a slow unraveling.

Florida City. The big green sign: “Key West — Straight Ahead.”
It felt like my lungs finally remembered how to work.

Past the Blue Wall—that stretch of 18 miles where mangroves hug the road and the sky feels like it’s spilling into the sea.
Key Largo’s dive boats bobbing in the marina.
Islamorada’s sandbars flashing turquoise in the sun.
Robbie’s Marina, where tourists toss fish to tarpon big enough to swallow a dachshund.

And then… Seven Mile Bridge. A ribbon of concrete floating between two oceans. Windows down, salt air whipping through.

Halfway across, Fred the Tree waved at me—rooted in nothing but stubbornness. I swear he knows the secret of life.

By the time I hit Mile Marker 0 in Key West, I wasn’t the same person.
I’d traded “what’s next?” for “what’s now?”

That’s the magic of the Keys.
Here’s where you can find it for yourself—mile by mile.

~ Brian

🌴 Bridge Moments — Seven Miles of Pure Freedom

There’s something about the Seven Mile Bridge that makes you want to turn the radio up and sing at the top of your lungs. Maybe it’s the way the horizon swallows the road. Maybe it’s the pelicans gliding beside you like winged travel companions. Or maybe it’s just knowing there’s no rush here. On this bridge, time moves at the speed of your heartbeat.

Pro tip: pull over at the Old Seven Mile Bridge in Marathon. Walk or bike out to Pigeon Key for history, views, and a reminder of how Henry Flagler once dreamed the impossible into concrete reality.

🐓 Roosters as Tour Guides — Key West’s Feathered Locals

You hear them before you see them. In Old Town Key West, roosters strut past pastel conch houses like they own the mortgage. They are, without question, the island’s unofficial greeters.

Some folks swear they crow all night just to mess with you. I think they’re just reminding you—sleep’s overrated when you’re in paradise.

Fun fact: Many are descendants of Cuban fighting roosters brought here in the 1800s. Now they just fight for your French fries.

🌊 Saltwater Soundtrack — The Seaports of the Keys

Every dock has its own rhythm. At Key Largo Harbor Marina, it’s dive boats loading up before sunrise. In Islamorada’s Bud N’ Mary’s Marina, it’s the slap of tarpon tails in the bait well. And at the Key West Historic Seaport, it’s rigging clinking against masts, seagulls laughing, and the occasional guitar drifting from Schooner Wharf Bar.

This is music you don’t need a playlist for.

🌅 Sunsets That Clap Back — From Islamorada to Mallory Square

In Islamorada, the Lorelei Cabana Bar turns every sunset into a beach party. Rum drinks in hand, toes in the sand, live music until the stars take over.

In Key West’s Mallory Square, you get a sunset and a circus—jugglers, sword swallowers, tightrope walkers, and an entire crowd that claps and cheers the second the sun dips into the Gulf.

Don’t miss the moment the sky turns cotton candy pink and the water mirrors it back—it’s the Keys taking a bow.

🌿 Mangrove Mazes — Hidden Worlds on the Water

In John Pennekamp Coral Reef State Park, rent a kayak and slip into mangrove tunnels so quiet you can hear your own paddle drip. The air smells like salt and earth, and every shadow feels like it could be a manatee.

Down in Big Pine Key, paddle the waters of the National Key Deer Refuge where the mangroves weave into labyrinths and herons stand like statues.

This is the Keys’ version of meditation—except the om is replaced with the splash of a mullet jumping.

🥧 Key Lime Everywhere — A Tangy Tradition

There’s the purist route: a slice from Mrs. Mac’s Kitchen in Key Largo, tart enough to make you pucker.
There’s the dessert-as-souvenir: chocolate-dipped frozen slices at Kermit’s Key West Key Lime Shoppe.
And there’s the “why not” version: Marker 88’s key lime martini.

In the Keys, key lime isn’t just dessert—it’s a food group.

☕ Cuban Coffee Queen Murals — Keys Time Starts Here

The Cuban Coffee Queen in Key West serves coffee so strong it might just rearrange your DNA. Grab a con leche and a breakfast sandwich, then take your photo in front of the giant postcard mural.

In Marathon, La Nina pours café Cubano with the same no-rush vibe. Sip slow, you’re not going anywhere fast.

🐕 Boat Dogs & Bar Cats — Furry Locals Who Rule the Scene

At Robbie’s Marina in Islamorada, cats sun themselves between the souvenir shop and the tarpon dock, completely unfazed by the tourist chaos. In Key West, Schooner Wharf’s dock dogs greet boats like they’re old friends.

In the Keys, if there’s a water bowl next to your bar stool, you’re in the right place.

🛶 Sandbar Days — The Keys’ Floating Parties

Just off Islamorada’s Holiday Isle Sandbar, the water’s waist-deep and the mood’s always high. Boats raft together, grills fire up, and someone’s always got a floating beer pong table.

For a quieter version, charter a boat to Nest Key in Key Largo—bring a snorkel, a cooler, and a hammock for the bow.

🎨 Island Art Stops — Creativity on Every Island

In Islamorada, Rain Barrel Village is a mix of quirky outdoor galleries and the famous giant lobster sculpture. In Key West, Gallery on Greene showcases works from Mario Sanchez to Peter Vey—pieces as colorful as the streets outside.

Art here isn’t something you find in a quiet museum—it spills out into the sunshine.

📅 Plan Your August in the Keys

August 8-9: Full Moon Kayak Tours — Paddle under moonlight through mangroves and open water.
August 29–Sept 1 (Labor Day Weekend): Buffett-style beach parties from Islamorada to Key West—details coming in our Labor Day special edition.

💡 Direct Booking Tip of the Month

When you book your stay directly with the resort or hotel, you’re more likely to score perks: free breakfast, better room upgrades, waived resort fees, and even late checkouts. Plus, you’re not sending a chunk of your vacation budget to a giant booking site.

That’s why we’re launching our new site FloridaKeysResorts.com this month, so stay-tuned— one place to find your favorite Florida Keys resorts, with direct booking links and no commissions skimming off your piña colada fund.

Looking for unbiased, fact-based news? Join 1440 today.

Join over 4 million Americans who start their day with 1440 – your daily digest for unbiased, fact-centric news. From politics to sports, we cover it all by analyzing over 100 sources. Our concise, 5-minute read lands in your inbox each morning at no cost. Experience news without the noise; let 1440 help you make up your own mind. Sign up now and invite your friends and family to be part of the informed.

Subscribe to 1440 today.