Whether you fly into Miami or Ft Lauderdale (we prefer Ft Lauderdale personally) or you drive from elsewhere in the US, the drive from South Florida through the Keys and into Key West is amazing, beautiful, and one not to be missed!
This is easily one of our top five favorite drives! As you cross over into the upper Keys, the traffic slows… the blue sky… the sunshine… the beautiful water… all of it combines to relax you into the Keys mentality. The drive through the Keys has been known to take a day, a few days, a week, or a lifetime! Once you’re in the Keys, you’re on Island Time! Relax, Go Slow, and don’t stress about the clock or the agenda!
However you arrive in South Florida, the first step is to set your compass south, via the FL Turnpike, towards Florida City. (You can order a Sunpass ahead of time if you want to avoid the cash toll lines along the drive.) When you get to the end of the Turnpike, make a Right onto West Palm Drive and head to Robert is Here Fruit Stand
for an amazing smoothie, as well as some fresh fruit and boiled peanuts to keep you satiated on the drive south! Get right back on the road, heading due south for Key West.
Your first (and likely only) navigational decision on your roadtrip will be which way to get to Key Largo — US 1 or Card Sound. If you choose Card Sound, be sure to have some cash in your wallet (a good decision in the Keys anyways). Your first official stop in the Florida Keys will be at Alabama Jacks! An old-school dive bar, Alabama Jacks is the perfect introduction to your Florida Keys adventure! Located on a canal, seating is outdoors, either covered or uncovered. Grab a drink and take a deep breath. Enjoy the music, the vibe, the views. Order the conch fritters if you’re feeling munchy, you’ll thank me later!
Back on the road, head through Key Largo, connecting back up with US-1. This is the only road through the rest of the Keys! As you head south, stop at Marker 88 for lunch (MM88 Bayside). This is a toes in the sand and a gorgeous water view type of place – laid back and beautiful, this is the Keys vibe that you’re looking for! Grab a drink and order a bit of food. Standouts here include the Hot Blue Crab Dip and the Blackened Tuna Sashimi.
Next, it’s off to the Tiki Bar at Postcard Inn Beach Resort. Legend has it that this is the birthplace of the Rum Runner, and we can attest to their Rum Runner and Rum Punch being some of the best we’ve had! Located Oceanside, the views of the blue ocean, as well as boats coming and going from the marina, make this a place that you could spend an afternoon at. However, you have many miles to go!!!
Your last stop in Islamorada is at Robbie’s to hand feed the Tarpon. This is a must-do for anyone who has not been to the Keys before, or who has not fed tarpon! These giant fish, sometimes over five feet long, have been “trained” by so many people feeding them at this location, and they will practically jump out of the water for your hand-fed snacks! Be sure somebody has a camera ready for that moment that the tarpon has his gaping mouth open at your hand!!!
Be sure to make a quick stop in Marathon for a slice of Deep Fried Key Lime Pie and boat watching at Burdine’s. This is one of our favorite stops on our Southernmost Trek! Coupled with some of their addicting french fries, this is a perfect mid-afternoon snack stop!
Cross over Seven Mile Bridge (wave to Fred the tree and his little partner Wilma on the old bridge!) and make a quick stop at Bahia Honda State Park to dip your toes in the water and learn a little history about all these bridges that you’re crossing!!! There aren’t words to describe the beauty of this State Park!
Make a quick detour on Big Pine Key to No Name Pub, “a nice place if you can find it!” Watch out for Key Deer as you make your way through the small streets and back to this hidden gem! No Name Pub has a storied history, including a bait and tackle, a general store, a brothel, a gambling hall, and intermingled later, a pub and eatery. Stop in, grab a beer (and a Keys-famous pizza if you’re hungry!), and tack a dollar to the wall!
Keep heading south (you’re getting closer)! Grab dinner at Hogfish Bar & Grill on Stock Island. It’s tucked away and takes a bit of navigating to find it, but it’s so worth it! We recommend the Lobster Bisque and any of the Hogfish dishes! Of course, a margarita rounds it out nicely 🙂 Once back in the car, you’re only about 10 minutes from Key West! Park your car and enjoy the rest of your trip!!!
While we have noted a few of our favorite “must stop” suggestions here, the length of the Florida Keys has so much more to offer! Please head over to our Facebook page, like it, and follow along on our adventures, which will help you to plan your adventures!!!! Be sure to also check out our longer articles on a bunch of these towns and islands for more detailed info on each! Happy trails!
Now that you’ve made it to Key West, check out our favorite things to do here! Click here!
Wondering where to find the best Key Lime Pie in Key West? Click here!
Recent Posts
The Florida Keys are special for a thousand reasons, and one of them is their famous dessert - the Key Lime Pie! With heavy input from our in-house dessert expert, Brianna, we have assembled our...
We first came to Key West in 2010. Since then, we have made dozens trips to this tropical Southernmost Town. Sometimes a quick weekend jaunt, and other times choosing to laze away for weeks on end....