A Mile-By-Mile Florida Keys Driving Guide To Bars, Restaurants & Waterfront Hangouts
This is one of PubClub.com’s original articles, dating to the website’s early days in 2001. It was created by two friends, Hayney and Laz, who would jump into a convertible and cruise down the Overseas Highway to Key West, stopping at their favorite bars, restaurants and waterfront hangouts along the way. They even timed their arrival for sunset at Mallory Square. The itinerary has been updated through the years to keep the information current.
By Hayney & Laz With Updates From Kevin Wilkerson, PubClub.com Editor & Publisher
The key to fully experiencing Key West is not contained in some local bar or in a moment at sunset on Mallory Square.
Instead, it is located some 100 miles to the northeast at the beginning of what is known as the Overseas Highway, a scenic two-lane road with water on both sides, 42 bridges and enough diversions to properly delay any trip to the Conch Republic.
For it is here that “Keys Disease,” that infectious virus that tempts every visitor to the southernmost city in the United States to stay far longer than originally intended, first takes hold in the system.
Oh, it’s possible to fly into Key West and its Caribbean outpost of an airport, but to do so misses so much of what makes this part of the world so special. So, too, is the shame for those who zoom down from South Florida without stopping to enjoy the many treasures along the way.
This area is knows as the Florida Keys, and it’s best enjoyed at a leisurely pace in a convertible. It has bars, restaurants, an underwater hotel and more dive shops than Los Angeles has fingernail salons.
Sports Illustrated once sent its models here for its annual swimsuit issue and now that the point has been validated, it’s time to make our way – slowly – to Key West.
Understanding Florida Keys Mile Markers: Bayside & Oceanside
Reference points are not the little towns that dot the Florida Keys, but instead the mile markers which line the highway. Without them, finding the proper places to stop would be virtually impossible. Mile markers are designed as MM, such as MM88.
Locals refer to places being “Bayside” and “Oceanside.” Bayside is on your right if you are headed south.
Starting The Drive: Florida City, Card Sound Road & Alabama Jack’s
The route to the Keys begins at the end of the Florida Turnpike in the tiny community of Florida City. It’s a good place to stretch the legs after the hour-plus drive from Miami. Jack’s fishing store on the right is a bait-and-tackle shop that has the best beer huggies, those rubber devices that fit around cans to keep beverages cold.
Just past Florida City, there’s a sign pointing to the left for Card Sound Road. Turn there. The road winds through an authentic Florida habitat with mangroves, pelicans, etc.
Longnecks and Fish Sandwiches
First among the many places to eat along the way is Alabama Jack’s. It comes up on the right just before the big old bridge along Card Key Sound Road. It’s a long-neck beer kind of place right on the water that serves a tasty fish sandwich.
The hard-core biker crowd can be a bit fishy, too, especially on sunny weekend afternoons, so approach with caution.
From there, make a right at the flashing light to get headed back to Key West.
At MM 102, the amicable staff at the Fish House serves true Florida fare, which grilled or fried seafood. The Fish House is one of the few restaurants that gets its fish fresh off the boats (most of the others get theirs from distributors).
The broiled yellowtail fish sandwich is so fresh it practically swims to your mouth.
Key Largo Stops: Seafood, Diving & The African Queen
Key Largo is straight out of a movie; scenes from the 1948 film of the same name starring Humphrey Bogart, Lauren Bacall and Edward G. Robinson were shot here. At MM100, the landmark to another Bogart movie is on display, the steamboat from “The African Queen.”
John Pennekamp Coral Reef State Park and the adjacent Florida Keys National Marine Sanctuary (formerly the Key Largo National Marine Sanctuary) make this area a haven for snorkelers and divers.
True enthusiasts can spend hours exploring life beneath the land without worrying about running out of air because, in a twist of Keys creativity, they can spend the night underwater.
Jules’ Undersea Lodge (305-451-2353) is the world’s only underwater hotel. Guests dive 30 feet to their room, located in the Emerald Lagoon. Each room comes with a true ocean view – out of a port window. Dinner of fresh lobster and fish is delivered by a diver. The rooms are fully equipped with a TV, air conditioning, showers, a stereo and a fully stocked galley. Guests are free to dive in the lagoon with its replica of a wrecked Spanish galleon.
Prices are not cheap but the hotel also offers three-hour visits, which includes unlimited access to the lagoon for certified divers. If you’ve got the money, this is the way to relax on the way to Key West!
Islamorada Bars & Restaurants: Mile Markers 88–84
The Mile Marker 88 restaurant serves authentic Florida food (fresh and fried seafood) in an ultra-friendly Keys style.
The Holiday Isle Tiki Bar in the town of Islamorda is a must-stop. It has “tourist trap” written all over it, but is a perfect rest stop. Swimming, jet skiing and other aquatic adventures await on its dock. And who can argue with the house drink specialty, the “Pain in the Ass,” a swirled combination of a pina colada and rum rummer.
There’s a hotel on the property, just in case one has too many pains to continue driving.
Just across from the Tiki Bar is the Whale Harbor. The food is average at best, but the bar is a good change of pace from the Holiday Isle.
Islamorada At MM82: Lorelei’s Waterfront Bar & Sunsets
Two miles further down the road sits Lorelei Restaurant And Cabana Bar, the best place in the Keys to watch the sunset. It’s nearly always crowded, primarily with locals, who enjoy sitting outside having cocktails next to the water.
At MM80, Papa Joe’s is another stop for Florida-style cuisine.
Marathon Restaurants: Conch Fritters & Waterfront Dining
Those looking for the Grassy Key Dairy Bar will be bummed that it closed (several years ago, in fact). This was a place that was recognized as having the best conch fritters in the Keys and was a frequent hangout of classic A-list celebrities, including Marilyn Monroe and Joe Dimaggio.
Instead, head south about five miles to The Island Fish Company in Marathon, where you will find great conch fritters. They have a good crust, are meaty and tender with just a bit of a kick. You get eight for 16 bucks.
There is also a tiki bar so you can have a rum drink to wash ’em down at a dockside table.
Where To Find A Lobster Reuben In Marathon
Here’s a unique Keys treat – a lobster reuben sandwich. It’s a like a lobster roll, except it’s served on thick, toasted bread with melted cheese. It’s as delicious as it sounds and as a bonus, you eat it on picnic tables at the water.
It comes with fries and can be found at Key’s Fishery Market & Marina (3502 Gulfview Ave., Marathon; bayside, at the end of 35th Street. The place also has a Konchwurst; bet you can’t get THAT anywhere else but there! If you want to hang for a while there is also an upstairs bar.
A Strong Cuban Coffee Stop In Marathon
Just beyond 35th Street, on the right in the Exxon station, is a place that serves the best – and strongest – Cuban coffee in the Keys. And perhaps the strongest anywhere outside of Havana.
One small cup will have you eyes opened wide your hair standing up as if you stuck a screwdriver into a light socket. It takes the Cuban lady time to make this little devil of a sin, so be patient.
Dockside In Marathon: Live Music & Waterfront Drinks
The biggest town in the Keys is Marathon and there are several places to eat and drink. The one the locals have loved for years is Dockside Tropical Cafe. It’s off the highway onto Sombero Road to Sombero Marina and with live bands nearly every night of the week and drinks from the BVIs such as a Bushwacker and the Soggy Dollar Bar’s legendary Pain Killer, and a deck that’s not just dockside it IS the dock.
Driving The Seven Mile Bridge & Exploring The Lower Keys
At about MM50 is the Seven Mile Bridge, the most scenic part of the trip. This “Keys connector” rises high above the land to expose expansive views of the water on each side, the Gulf of Mexico to the west (right, on the way to Key West) and the Atlantic Ocean to the east.
It’s actually 6.79 miles and in 1982, 37 of the original bridges, including the Seven Mile Bridge, were replaced with wider spans. This is where Jimmy Buffett finished writing his landmark song Margaritaville. As he told the story he started the song in Austin, Texas where he had a margarita to help fight off a hangover and then when headed back to Key West got caught in a traffic jam for two hours because of an accident on the bridge. When he got to the Conch Republic he played his new song during a gig at the bar and people asked him to play it again. “They seem to kind of like that song,” he said himself.
Many of the old bridges still can be seen running alongside the newer ones.
The Seven Mile Grill offers good food and drink and just across the highway at MM32 on a side road is another bar/grill called the No Name Pub, famous for its dollar bills on the walls and pizza (note: this is 15 or so minutes off Highway 1, bayside, at Mile Marker 30.5 on Pine Key).
At MM20 is Mangrove Mama’s, a cool bar – well a mangrove shack, really – with excellent food served in a tropical setting and home of the best Key Lime Pie in the Florida Keys. If you get a sandwich get it with the “true Southern” potato salad. Sunday nights, it’s got the best reggae band in the Keys. It’s only a 20-mile drive from Key West, so much of the Sunday crowd is from the Conch Republic.
The Final Miles To Key West
Still hungry? Bobalu’s Southern Cafe, is a family-operated road house at MM8.
After that, it’s a straight shot into Key West.
Driving From Miami To Key West: Frequently Asked Questions
How long does it take to drive from Miami to Key West?
The drive is approximately 160 miles and takes around 3½ to 4 hours without significant stops, depending on traffic and your starting point. But PubClub’s advice is to allow most of the day. The stops along the Overseas Highway are what make this one of America’s great road trips.
What are the best places to stop between Miami and Key West?
For the PubClub experience, start with Alabama Jack’s on Card Sound Road, explore Key Largo, stop for waterfront drinks in Islamorada, enjoy seafood in Marathon and take in the scenery around the Seven Mile Bridge. The best stops aren’t necessarily the biggest attractions; they’re the places where you can settle into the Keys lifestyle.
Is the drive from Miami to Key West worth it?
Absolutely, especially if you enjoy waterfront restaurants, tropical scenery and laid-back bars. Driving gives you the opportunity to experience the different personalities of the Florida Keys instead of simply arriving in Key West.
What is the best time to drive from Miami to Key West?
Start in the morning and travel during daylight so you can enjoy the scenery and make stops along the way. Allow additional time during busy travel periods. If you’re following the original Hayney and Laz itinerary, the goal is to reach Key West in time for sunset at Mallory Square.
How do mile markers work in the Florida Keys?
The Overseas Highway has numbered mile markers that descend toward Mile Marker 0 in Key West. Locals use them to identify restaurants, bars, businesses and neighborhoods. You’ll also hear “bayside” and “oceanside” when asking for directions.
Kevin Wilkerson is the founder of PubClub.com, an award-winning journalist and nightlife expert who has covered destinations, events and nightlife for more than two decades. While working as a newspaper reporter, he received an Associated Press award for investigative journalism.
Next Stops On The Florida Keys Party Bus…
• Oh My Gawd: I’ve Got Keys Disease!
• Top 5 Things To Know While Driving In The Florida Keys
• Key West Travel & Orientation Guide
The Seven Mile Bridge is indeed an iconic landmark of the Key West drive!