Where to Stop and Eat on the Drive From Miami to Key West

Sometimes an island escape is necessary, but the hassle of flying and other major travel plans is a deterrent. Luckily for Miami the Florida Keys are right down the street. The Southernmost point, Key West, is an easy 3.5 hours away but upon arrival it feels a million miles from home. The drive through the Florida Keys includes hundreds of tiny islands, 42 different bridges to cross over, and tons of food stops along the way. Expect to find dishes like conch fritters, some of the freshest seafood around, and key lime pie galore.

It’s a land of dive bars and live music and everyone seems to be having the time of their life. Don’t be in a rush to try it all right away, be on island time. Get ready to take it easy and enjoy life with a daiquiri in hand.

Below is a play by play of where to stop on the way to and from Key West from Miami.

Obligatory Shake Stop: Robert Is Here Fruit Stand

A trip through Homestead is nearly impossible without a stop at Robert Is Here (19200 SW 344th St, Homestead). He started out with a little card table, a few cucumbers and a sign proclaiming “Robert Is Here” and now, more than 50 years later, everyone has beat a path to Robert’s door. Grab some tropical fruit to go and a shake before hitting the road. Flavors change constantly depending on the season, but no matter what shake is ordered, it’s hard to go wrong.

Scenic Route Snack: Alabama Jack’s

Card Sound Road may have a $1 toll, but it’s worth it for the more scenic views and to make a pit stop at Alabama Jack’s (58000 Card Sound Rd, Homestead). It’s a divey spot known for its conch fritters, live music and breezy atmosphere. Stopping at Alabama Jack’s is rite of passage for anyone’s first trip to the Keys — along with an order of its smoked fish spread.

Lunch: Mrs. Mac’s Kitchen

Key Largo's Mrs. Mac’s Kitchen (99336 Overseas Hwy, Key Largo) is always a classic stop once in the Upper Keys. Surrounded by down home décor of license plates hanging on the walls along with historical mementos and pictures, it serves classic American dishes with a Keys twist like lobster bites and conch salad, plus an extensive breakfast menu featuring a must-try caramel bacon French toast.

Frozen Cocktails: Tiki Bar at Holiday Isle

A stop at the Tiki Bar (84001 Overseas Hwy, Islamorada) means the trip has lasted long enough and it’s time for a fruity frozen beverage. Sit right on the ocean while sipping one of its “World Famous Frozen Rum Runners” and listen to live music, or try out a Miami Vice made with half strawberry daiquiri and half pina colada. Drinks aren’t the only thing on the menu, which features fish sandwiches made either fried, grilled or blackened along with dishes like fish tacos, peel ‘n eat shrimp, and shucked oysters.

Happy Hour: Sloppy Joe’s

A trip to Key West is not complete until stopping into Sloppy Joe’s (201 Duval St, Key West). The bar, which opened the day Prohibition was repealed in 1933, is one of the most historic bars in the country. A favorite of Hemingway’s, who actually suggested the name “Sloppy Joe,” it’s still a popular waterhole all these years later. Order some conch fritters and a cocktail to fit right in while listening to the live local bands that play all night long. Get there early enough and walk over to the sunset festival that takes place right across the street with entertainers and street performers putting on shows as the sun sets over the island.

Dinner: Mangoes Key West Cuisine

Mangoes Key West (700 Duval St, Key West) has been around for decades and is located right in the middle of Old Town Key West. Ask to sit on the patio for some prime people watching of Key West at night while dining on the Bahamian-style snapper and Cuban seafood stew.

Dessert: Better Than Sex

Save room for dessert because Better Than Sex (926 Simonton St, Key West), a dessert-only restaurant, is a must do while in Key West. Think chocolate covered cocktails and massive slices of cake. The experience at Better Than Sex can be as fun or as romantic as one wants it to be, just know a sugar high is bound to happen.

Hearty Hangover Breakfast: Harpoon Harry’s

This cash-only diner is the perfect place to come back to life after a long Key West night. On the menu at Harpoon Harry’s (832 Caroline Street, Key West) are biscuits and gravy, build-your-own omelets, and every other breakfast staple that could possibly craved after a long night. Plus, there’s no need to wake up early as Harpoon Harry’s serves breakfast until 3 p.m.

Pie For The Road: Kermit’s Key Lime Pie Shop

Kermit's Key Lime Pie Shop (802 Duval Street), owned by Kermit Carpenter, is a Key West institution. It’s not rare to see him stand outside his brightly painted yellow and green store throwing pies at people for fun. The pies are light yet creamy, with the option to get a piece dipped in Belgian chocolate. But pie isn’t the only key lime creation being sold here, there also other items fudge, jelly, salsa, and soaps, making it a good pit-stop to stock up on treats to take home.

Late Lunch: Snappers Key Largo

It’s the last stop before returning to reality and there are two options — eat in the Snappers Oceanfront Restaurant and Bar (139 Seaside Ave, Key Largo) where things are a bit more upscale or hang with the locals in the back at the Turtle Club and keep living the island life. If picking fancier fare, check out the wahoo ceviche and the shellfish scampi. Still living like an islander? Sit at the Turtle Club outdoor bar. Order Snappers’ tuna nachos or the beer battered mahi sandwich.