~ Everybody has their favorite pit stops when traveling through the Florida Keys on the Overseas Highway. It may be a tiki bar for the first rum-runner of the weekend, or a quick bite of home-made chow topped off with Key Lime pie.
It’s a Keys tradition.
The prerequisites for making our list are good food, easy access to the highway and you can get in and out quickly, or as quickly as you can, considering you are in the Keys.
Life kinda meanders here. At a snail’s pace. But isn’t that why you came?
Updated February 2019
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HOBO’S — MM 101.5
Hobo’s has lost some of its charm since moving from its cozy, railroad-car origins across the street, but the food may actually be better. The larger kitchen has also fed a bigger menu. Their New England clam chowder is among the best to be had, forever, and everyone should try the dolphin (mahi mahi) reuben just once. In fact, you can’t go wrong with any of their fresh fish, all of it local. But the real reason we stop here is for the burgers. On a nice day, sit on the patio.
MRS. MAC’s KITCHEN — MM 99.4 (the original) and MM 99.0 (Mac II)
One Mrs. Mac is not enough, so the proprietors of Key Largo’s favorite eatery have opened up Mrs. Mac’s Kitchen II just a hop and a skip down the highway, making Mrs. Mac’s legendary chow accessible to both sides of the divided Overseas Highway. Fresh fish and grits is a standard, possibly outdone only by the blackened lobster and grits for breakfast. Moderately priced, the lunch menu runs the full gamut of Keys dishes with several takes on the fish of the day. Mrs. Mac’s dinner table is set with a variety of fish dishes and fried baskets, from cracked conch to alligator bites. Mrs. Mac lays claim to the best Key Lime pie anywhere, but so does everybody else. You be the judge.
HARRIETTE’S DINER — MM 95.7
After the divided Overseas Highway rejoins in Key Largo, there’s an unpretentious yellow shack on the right that is practically world famous and a favorite of locals. Some will tell you that there is no better place in the Keys for breakfast than Harriette’s. Everything they serve is homemade. Try their Key Lime muffins and/or their traditional southern breakfast offerings. Service is great, and the prices are budget-friendly. Goes to show that you can’t always judge a diner by it’s paint job.
TWISTED SHRIMP — MM 87.7
A recent addition to our roundup, this new Keys roadside eatery has quickly racked up a reputation for its fried shrimp, shrimp tacos and shrimp ’n grits. The moderately priced menu also features some “Good Ole’ Jambalaya” with sausage and mahi mahi (optional). For a killer desert, try the chocolate-dipped Key Lime on a stick! The Twisted Shrimp is a shrimp-heavy adventure in Keys cuisine and a welcome newbie with instant Keys karma.
For more landmarks along the Overseas Highway, check out our fabulous Florida Key Mile-Marker Guide
LORELEI — MM 82
If you are driving by at sunset — or any time, really — pull off the Overseas Highway at the mermaid sign on the bay side near Mile Marker 82. Beyond the parking lots, Lorelei’s decks, chickee huts, palm trees and sandy waterfront create an expansive sunset view over the mangrove-lined bay. The menu is typical Florida Keys, but at sunset, with a band playing seven nights a week, the Lorelei is anything but typical. It’s the “pulse of Islamorada.”
ISLAMORADA FISH COMPANY — MM 81.5
This is the original Islamorada Fish Company, which has now aligned itself with Bass Pro Shops with locations all over the country, including Fort Lauderdale. A popular seafood market is out front, and the restaurant and sunset tiki bar are out back, part of the neighboring Worldwide Sportsman, the temple of fishing owned by Bass Pro. The restaurant has its own fishing fleet, so the fish is fresh off the boat.
HABANOS — MM 73.5
This clean and spacious diner at the Caloosa Cove Marina on Lower Matecumbe Key has gone through a few transitions over the years, but its latest incarnation is a keeper. As the name suggests, the featured cuisine is Cuban, among the best in the Keys, and the prices are very reasonable. Bring your own catch, and they’ll grill it to perfection. Get a table in the rear dining area with big windows overlooking the marina. Habanos is a regular lunch stop for blue-collar Cubans working along the highway, and that should tell you something.
THE ISLAND FISH CO. — MM 54.5
Having undergone post-hurricane remodeling, the Island Fish Co. is no longer home to the Keys’ longest tiki bar. But this fabulous open-air eatery is now open for breakfast, lunch and dinner. We found the prices reasonable, not to mention quite tasty. We LOVED the Indian River Steamers, a baker’s dozen (we got 15) littleneck clams served in its own broth. (Ask for fresh bread to dip.) You’ll want to try everything on the menu, from the Jalapeño corned beef hash for breakfast to the Dolphin (mahi maxi) Pico de Gallo at lunch or dinner. And you’ll love the open-air views of the marina from every table.
WOODEN SPOON — MM 51
One of my two favorite breakfast stops in Marathon, the other being The Stuffed Pig. A variety of tasty breakfast dishes include Oatmeal with raisins, banana and blueberries, a variety of tasty omelets ranging from veggie to meat lovers, French toast with fruits and nuts. Don’t skip the biscuits! Best biscuits in the Florida Keys. 7007 Overseas Hwy, Marathon.
THE STUFFED PIG — MM 49
The Stuffed Pig is my other favorite breakfast stop in Marathon (Wooden Spoon being the other.) Whenever I’m in the Keys, I look for restaurants that serve flaky, battered fish fillets with my eggs, which is why I love this place. But if you’re a hog, try the namesake Pig’s Breakfast: 2 pancakes, 2 eggs, 2 bacon, 2 sausage, home fries, and toast. I also have to admit to a weakness for their country fried steak and eggs (sorry, Porky).
PORKY’S BAYSIDE — MM 47.5
A funky open-air BBQ joint on the bayside just before the 7-Mile Bridge, Porky’s has been around since the 1950s and still holds its own as a classic Keys eatery. Besides a variety of pork BBQ dishes (smoked daily), try the Pina Colada Coconut Shrimp for an appetizer. In addition to Porky’s excellend BBQ, you’ll find a pleasing selection of fresh local seafood on the menu. If you don’t have time to linger through Porky’s famous Happy Hour, grab a moho marinade Cuban sub for the road.
7 MILE GRILLE — MM 47
This landmark eatery is at the foot of the Seven Mile Bridge in Marathon. I wouldn’t necessarily tag it as having the best road food, but it is good enough “Keys food” with fresh local fish and the prices are moderate to a point. The entrees can get pricey, considering it’s road food, but the sandwiches and burgers are priced right. At the 7 Mile Grille, the appeal is the ambiance and view, and with the beautiful world-famous bridge stretching ahead of you. The view is a winner.
PIZZAWORKS — MM 30.2
This cozy New York-style pizzeria is just off the highway in the Big Pine Shopping Center. At Big Pine’s only traffic light, follow Key Deer Boulevard a short hop to the Winn-Dixie shopping center, also headquarters of the Key Deer Wildlife Refuge. From its famous calzones to its modestly priced pizzas with an awesome crust, Pizzaworks is a welcome waypoint on the Overseas Highway at 229 Key Deer Blvd.
MANGROVE MAMA’S — MM 20
I would be remiss not to include Mangrove Mama’s on this list, although I honestly have never stopped here. However, everybody else in the world has dined here, and they keep going back, so it must be good. This restaurant is as Keysy as it gets, serving cracked conch and conch chowder, blackened dolphin bathed in blue cheese, coconut-encrusted grouper and a variety of fried seafood baskets. No meal here is complete without Mama’s famous Key Lime pie.
BABY’S COFFEE — MM 15
If you’re not drinking Baby’s Coffee, then your just drinking coffee. Still recovering from near-destruction after Hurricane Irma, Baby’s is a survivor in the Keys tradition. You can still buy their fresh-roasted beans from a nondescript shack on the ocean side at Mile Marker 15. There are two locations, the other being in Louisiana. Once you’ve had a taste, you’ll be back for more. And more. In fact, you can order online and they’ll ship it to you.
The road may end in Key West, but not the road food. Check out this article: 8 Key West restaurants for authentic local flavor.