~ 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 that you have to be able to see the place from the highway and get in and out quickly, or as quickly as you can, given that it’s the Keys.
Life kinda meanders here. At a snail’s pace, in fact. But isn’t that why you’re here?
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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 they serve 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 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.
MRS. MAC’s KITCHEN — MM 99,4
A favorite of locals, Mrs. Mac’s Kitchen is a legendary Key Largo eatery. 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 and everything in between. Mrs. Mac also lays claim to the best Key Lime pie anywhere, but so do the rest of these fine dining establishments. You be the judge.
HARRIETTE’S DINER — MM 95.7
Just after the southbound Overseas Highway splits 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 home-made. 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.
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 and outstanding 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 is out in back of 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.
GRASSY KEY OUTPOST — MM 58
We haven’t visited the Grassy Key Outpost, but my nephew raves about it, and so do the reviewers on Yelp! My nephew stops here after burning wakeboard at the nearby Keys Cable Park. “Best food in the Keys,” he says. Prices are moderate, and the menu features Keys favorites with a Carolina low-country twist. Shrimp and grits, anyone? Maybe the fried green tomato BLT. For breakfast, you might consider the black bean, chorizo and egg burrito with fresh avocado. Prices are moderate. Let us know what you think.
The Stuffed Pig is one of my two favorite breakfast stops in Marathon, the other being The Wooden Spoon. Whenever I’m in the Keys, I look for restaurants that serve flaky, battered fish filets 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).
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.
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. Beans are roasted fresh daily, and you buy it fresh at their little nondescript cafe on the ocean side at Mile Marker 15. There are two locations, the other being in Louisiana. But the beans are roasted and packed on site. Once you’ve had a taste, you’ll be back for more. And more. In fact, they’ll even ship it to you. The black-and-white cookies may also be the best you’ve ever tasted.
The road may end in Key West, but not the road food. Try 8 Key West restaurants for authentic local flavor.