🛣️ Mile Marker Magic: The Quirkiest Roadside Stops from Miami to Key West

Dear Road Trippers,

There’s something magical about heading south from Miami, past the Everglades, onto that fabled stretch of road where land and sea blur into turquoise horizons. The Overseas Highway isn’t just a scenic route—it’s an adventure. And while everyone talks about the sunsets and the seafood, it’s the quirky, charming, and totally weird roadside stops that give this trip its true soul.

So this week, we’re highlighting our favorite Mile Marker magic—a guide to the must-stop, must-snap, and must-taste moments from Key Largo (MM 106) to Key West (MM 0).

Buckle up, roll the windows down, and let’s ride 🛻💨

🌿 MM 106 – Dagny Johnson Key Largo Hammock Botanical State Park

Start with serenity. This park protects one of the largest remaining tracts of West Indian tropical hardwood hammock in the U.S. Paved trails make it easy to explore for all ages and accessibility needs. Keep an eye out for butterflies, rare birds, and the elusive American crocodile!

🕒 Open sunrise to sunset
💰 $2.50/person
📍 More Info

🧬 MM 102.5 – John Pennekamp Coral Reef State Park

You haven’t truly seen the Keys until you’ve seen beneath them. 🐠 Dive or snorkel among living coral reefs, hop a glass-bottom boat tour, or paddle through mangrove tunnels. It’s part marine reserve, part underwater museum, and totally unforgettable.

🕗 8 a.m. to sunset
💰 $8/vehicle
📍 More Info

🦞 MM 86.7 – Betsy the Giant Lobster (Islamorada)

She’s 30 feet of fiberglass, claws raised like she’s ready to high-five your road trip spirit. 🦞 Standing outside Rain Barrel Village, Betsy has become the most photogenic crustacean in Florida. Snap a selfie, grab a coconut drink, and browse the artist stalls.

📍 Rain Barrel Village
📸 Instagram gold

📚 MM 82.1 – History of Diving Museum (Islamorada)

Don’t skip this gem! It’s one of the most surprisingly awesome stops on the trip. With antique dive helmets, old-school gear, and weird deep-sea artifacts, you’ll leave with a whole new appreciation for ocean explorers.

💡 Don’t miss: the evolution of underwater breathing exhibit
📍 History of Diving Museum

🪵 MM 77 – Anne’s Beach (Lower Matecumbe Key)

A peaceful pit stop with boardwalks, shaded picnic tables, and shallow swimming spots. It’s free, relaxing, and perfect for stretching your legs after an hour in the car. Great for kids, dogs, and hammock selfies.

🚗 Parking available (can fill up quickly)
💧 BYO towel and snack
📍 Anne’s Beach

🐬 MM 61 – Dolphin Research Center (Grassy Key)

Ready to meet a dolphin? 🐬 This nonprofit education and research center offers interaction programs, dolphin shows, and sea lion chats. It’s heartwarming, educational, and a huge hit with families.

🎟️ Reservations recommended
📍 Dolphin Research Center

🌴 MM 59 – Grassy Flats Resort & Ohio Key Viewpoint

Whether you’re staying overnight or pulling off for the view, this eco-resort gives you front-row seats to one of the best views on the Overseas Highway. Great spot for a sunset stop, drone shot, or spontaneous picnic.

📸 MM 59 bridge pull-off
📍Grassy Flats Resort

🐢 MM 48.5 – The Turtle Hospital (Marathon)

Stop here and fall in love with sea turtles. 🐢 This fully operational hospital rescues and rehabilitates injured sea turtles from across the Keys. The tours are fascinating—and your visit supports the work!

🎟️ Book ahead for the guided experience
📍 The Turtle Hospital

🌳 MM 41.5 – Fred the Tree (Old Seven Mile Bridge)

A lone tree growing from a crack in an abandoned bridge. No soil, no help, just pure Keys resilience. Fred is a fan favorite—especially around Christmas, when locals light him up in twinkling lights.

📸 Best viewed heading southbound after the Seven Mile Bridge
🎄 Read Fred’s story

🍻 MM 30.2 – No Name Pub (Big Pine Key)

“Get lost. Find No Name.” That’s their motto, and it’s worth the detour. This legendary dive is covered in thousands of dollar bills, serves killer fish sandwiches, and is your best chance to spot a Key deer in the wild.

🍔 Try: Grouper sandwich + a cold beer
📍 No Name Pub

☕ MM 15 – Baby’s Coffee (Rockland Key)

Need a caffeine fix? This local roaster has been fueling road-trippers for years. Grab an iced con leche and check out the funky T-shirts and bumper stickers. It’s funky, fun, and fueled by the island spirit.

🛍️ Great place to stock up on travel snacks
📍 Baby’s Coffee

🛥️ MM 0.5 – Key West Historic Seaport Harbor Walk

You’ve made it to Key West—don’t stop just yet. Wander this scenic waterfront stretch filled with sailboats, seafood shacks, art galleries, and lively tiki bars. It’s the perfect wind-down to your adventure.

🛳️ Mallory Square is just around the corner
🖼️ Art & shopping galore

🍸 MM 0 – The World’s Smallest Bar (Duval Street, Key West)

You can blink and miss it—but don’t! This 6-foot-wide bar might be the tiniest in the U.S. Step inside, order a rum shot, and mark the end of your trip with a drink in true Keys fashion.

📍 Between larger shops on Duval Street
📷 A must-grab photo moment

💬 Tell Us Your Favorite

What’s your favorite Keys roadside stop?
📩 Reply to this email and let us know—we’ll feature our favorites in next week’s newsletter!

Until next time—may your camera be ready, your cooler be stocked, and your road trip full of mile marker magic.
See you at the next stop,

Brian
Florida Keys Road Trip Team