Miami to Key West Road Trip: A Four-Day Itinerary

While I can’t say Florida is my favorite place in the United States — it’s far from it, honestly — our road trip to the Florida Keys remains a highlight years later. 

Miami’s fun, but the moment you leave the city’s chaos and hit the Overseas Highway, it’s a different vibe altogether. 

There just aren’t many stretches of road where you’ve got turquoise waters on both sides of your car. 

The slow pace is a major mental switch from a lot of the rest of the country, which makes for the perfect road trip. 

This four-day itinerary for a Miami to Key West road trip details how we approached our first visit to this part of the state. This wasn’t a beach vacation, but a moving postcard, basically.

Is the drive from Miami to Key West worth it?

The drive from Miami to Key West is absolutely worth it if you love a scenic road trip and slower travel. The Overseas Highway offers long stretches of turquoise water, island hopping, and iconic stops like the Seven Mile Bridge that you won’t get if you fly.

How to Plan Your Road Trip to Key West

Planning a road trip to Key West is pretty straightforward. The most scenic and iconic route is the Overseas Highway (U.S. Route 1), which strings together the Florida Keys with open water views almost the entire way.

The total distance from Miami to Key West is about 165 miles, and while you could drive it in roughly four hours, that’s missing the point. This is a route meant for detours, long lunches over conch fritters, and pulling over just because you like the view.

Miami to Key West: The Ideal Road Trip Itinerary 

Our four-day Miami to Key West drive looked like this:

• Day 1: Miami to Islamorada
• Day 2: Islamorada to Key West
• Day 3: Key West
• Day 4: Key West to Miami

Day 1: Miami to Islamorada

This Florida Keys itinerary doesn’t include much time in Miami, other than it’s where you start and finish your trip. You’re here to focus on the Florida Keys.

If you’d like a city break as part of your Florida trip, add a day or two to the front or end of your Florida Keys road trip. Miami is fun, but it’s a completely different vibe.

I’d suggest starting your trip there while the energy’s high, rather than spending days in Miami at the end of your trip when you’re all relaxed. If it’s a quick pass through, I’ll include some ideas for dinner in Miami if you have some time on the backend.

On your first driving day, you don’t need to start too early, as you can get to Key Largo in under an hour.

Note: I’ve seen some bloggers recommend a quick stop at Everglades National Park before you drive down, but realistically, you’d need at least a full day to experience it properly.

Stop 1: Alabama Jack’s

Our first stop was Alabama Jack’s, a waterside spot famous for conch fritters. The food isn’t Michelin-level, but it’s a good excuse to stretch your legs and watch the water.

We shared a platter of fritters, naturally, alongside their blackened fish and crab cake sandwiches. It all felt very much like the kind of place that makes you feel like you’ve officially hit the Keys, with a mix of locals and tourists. 

Grab a seat on the deck if you can and sip on something cold. If you’re lucky, you’ll be able to watch some boats drift by as you crunch on those fritters. 

Stop 2: John Pennekamp Coral Reef State Park 

This park is home to the only living coral reef in the continental U.S. You can snorkel, dive, or take a glass-bottom boat tour if you prefer to stay dry. Even a short walk along the mangrove trails gives you a taste of the unique coastal ecosystem.

Snorkeling here was another real “we’re in the Keys” moment for us. Think colorful coral, fish everywhere, and that sense of being somewhere almost otherworldly. 

If you plan to do the same, book your tour early and show up on time. Despite the slow pace in the Keys overall, the park is popular and moves efficiently.

For more nature, the Florida Keys Wild Bird Rehabilitation Center is just a short drive from the park. It’s a lovely, low-key stop to see rescued birds and learn more about the local wildlife. Visits are free, but donations are accepted. 

The Dagny Johnson Key Largo Hammock Botanical State Park is another option. This peaceful forested area has a few short trails to take advantage of if you have more energy to burn after your snorkeling.

Stop 3: Mrs. Mac’s Kitchen

Assuming you’ve worked up an appetite for a treat, make a quick detour for dessert once you’re done swimming with the fishies at Mrs. Mac’s Kitchen. 

This is a local go-to for Key lime pie, sweet and tart, right out of a little pink-tinged diner. The shop is unpretentious, with classic Florida Keys casual décor. Grab a slice to take with you or, better yet, take a seat. 

Note: You’re probably not ready for more real food yet, but Mrs. Mac’s Kitchen also serves up breakfasts, sandwiches, and seafood plates for the peckish out there.

Stop 4: Robbie’s Islamorada

By late afternoon, we continued south to Islamorada, a compact string of islands where the pace slows even more dramatically. Islamorada is under half an hour from Key Largo.

The most popular stop here by far is Robbie’s, where you can feed massive silver fish known as tarpon that jump out of the water for their snacks. Honestly, relatable.

For a couple of bucks, you get a bucket of fish and access to their dock, where locals, kids, and first-timers all line up to feel something. It’s chaotic, loud, and feels super touristy, but I promise you this tradition is a beloved one.

Check out a short clip of what it’s like below:

Beyond the spectacle, Robbie’s has a small waterfront market, a bar, and a casual restaurant. We didn’t eat here because the food sounded just OK, but we spent some time wandering around to watch the boats and pelicans scrounge for scraps.  

Stop 5: Dinner

Our pick for dinner was Lazy Days Restaurant. More ocean views and more seafood awaited at this low-key (I will say that a lot in this guide) destination. 

The Hungry Tarpon was an alternative on our list. They have cook-your-catch options available for the more aggressive travelers out there.

I found that food overall along the way was more about the views than what you’re putting in your mouth. We never went hungry, but I wouldn’t return to the region for the food alone. I’d come back for the uniqueness of this place, though, for sure.

If you’re following along with me here and continuing to Islamorada, we checked into the Breezy Palms Resort for the night. It was low-key (there it is) but charming with a private beach area.

For more accommodation options in Islamorada, check out the map below:

Day 2: Islamorada to Key West

You can get to Key West from Islamorada in under two hours, but you’ll pass some big stops along the way. Don’t rush this day. This stretch is meant to be relaxed and scenic, especially once you see the open water on both sides of your car. 

Your first couple of stops are in Marathon, just under 40 minutes from Islamorada, so you don’t need too early a start, either. It fits the narrative of this part of the country, all leisurely like.

Stop 1: Wooden Spoon

The Wooden Spoon is casual, quirky, and the perfect place for a lead-in to Key West, a town that is BIG on quirk.  

This small diner in Marathon leans into its retro personality, with wooden spoons covering the walls.

We always love a breakfast sandwich, but you can expect all of the comfort food classics. The portions are generous, too, so you can split something if you’re not big on morning eating.

Stop 2: The Turtle Hospital

This was one of the most memorable stops of our trip. The Turtle Hospital, also in Marathon, offers a 90-minute guided experience that we found both educational and moving. 

You’ll learn about local sea turtle conservation efforts and get a behind-the-scenes look at the rehabilitation pools. The stories about how each turtle ended up there can get pretty sad.

At the end, guests are invited to feed the permanent residents, but don’t expect to swim or otherwise interact with them. Arrive a little bit ahead of your reservation time to get yourself checked in. Planning around this one is worth the effort!

Stop 3: Seven Mile Bridge

Leaving Marathon, you’ll cross one of the most iconic stretches of road in the Keys. This is the good stuff. Driving over the Seven Mile Bridge is a surreal experience, with uninterrupted blue water stretching out in every direction.

READ MORE: This bridge isn’t scary, but read about one that is: the Lake Pontchartrain Causeway.

As you cross, you can see the original bridge running alongside it. Completed in 1912, it was once considered the “Eighth Wonder of the World,” and it’s easy to see why. 

If you want to stretch your legs, you can pull off near the Old Seven Mile Bridge at the Marathon side.

Part of the historic bridge is open to pedestrians and cyclists, making it one of the few places where you can walk out over open water without committing to a full hike. 

There are no services once you’re on the bridge itself, so this is more of a stop-and-soak-it-in moment than a linger-all-afternoon situation. Still, it’s worth slowing down for. This drive is one of the main reasons people do the Keys by car in the first place.

Stop 4: Bahia Honda State Park

Just beyond the bridge, Bahia Honda State Park is a perfect excuse to get out of your car. This is one of the prettiest beach areas in the Keys. 

Snorkeling tours weren’t running during our visit due to some hurricane damage, but you can do more of that here if conditions allow. 

Even without getting in the water, it’s worth stopping for a beach stroll, a swim, or just lying out and doing absolutely nothing for a bit. There are also short nature trails and picnic areas here if you’d rather stay dry.

Fun fact: Bahia Honda was once a key stop along Henry Flagler’s Overseas Railroad, and you can still see remnants of the old rail bridge rising above the park. It’s a quiet reminder of how ambitious this route once was.

There’s a small entrance fee to access the park, but it’s money well spent for a few hours’ worth of a scenic reset before the final push toward Key West.

Stop 5: No Name Pub

As you haven’t eaten since breakfast, even if it was an indulgent start, it’s probably time for a nosh. 

The well-worn dive bar in Big Pine Key is the oldest in town, and is covered with dollar bills left by travelers over the years. The food is pub fare, the drinks are cold, and the atmosphere is zero f*cks given. 

Share a pizza or one of their two-handed pub burgers, followed by more key lime pie if you have the room. This one is a fun contrast to the beach stops I’ve recommended so far. 

Stop 6: Key West

From here, it’s a little under an hour to Key West. The drive is straightforward, but we definitely felt an energy shift the closer we got.

Things are a little livelier in Key West, especially compared to the quiet stretches you have just passed through.

If you want to hit the town, the Sunset Celebration at Mallory Square is a classic first-night stop.  Every night as the sun starts to dip, street performers, musicians, and food vendors line the waterfront as people gather to watch the sun set. 

It’s a great way to soak up Key West’s personality without much planning for your first night. From here, it’s an easy walk to Duval Street if you want to keep the night going. 

We had a pretty late lunch this day after an indulgent breakfast, so dinner wasn’t on our minds. An option nearby for small bites, though, is Santiago’s Bodega. It’s a cute tapas bar with hot and cold plates. I’m generally a sucker for patatas bravas in these situations.

For your overnight, we recommend the Truman Hotel downtown. You’re a short walk from all of the fun along Duval Street and the Hemingway House, a major highlight I’ll get into on your third day.

Assuming the weather allows it, there’s a great pool that we enjoyed relaxing in after full days of exploring, and the included breakfast is decent.

If you want to browse a bit more, check out the map below for more apartments and hotels in Key West:

Day 3: Key West

After two days of driving and snack-based decision-making, this day is all about being in Key West. The island is only four miles long, so you don’t even need to get too aggressive with your must-sees in town.

Although we only spent a few days here ourselves, it’s easily our favorite city in Florida. We like things a little weird, I suppose. It suits us.

Stop 1: Southernmost Point Buoy

Kick off your full day in Key West with a quick stop at the Southernmost Point Buoy. It’s super touristy, but one of those things you just have to do.

Snap a photo that lets everyone know you were just 90 miles from Cuba at this point in time, then move on.

Stop 2: Pepe’s Café 

Key West does breakfast well, especially if you lean into its Cuban and Caribbean influences.

Pepe’s Café is the classic choice, and it just so happens that it’s also the oldest choice in the Keys. It’s the second-oldest restaurant in the entire state of Florida, so you’ll be indulging in some history alongside your grub.

Expect classic diner fare no matter when you’re here. We went with more of a lunch vibe just because we arrived later in the day, but you can never go wrong with a side of corned beef hash.

Stop 3: The Ernest Hemingway Home & Museum

This is Key West’s most famous attraction, and it was our favorite stop during our trip. Even if you’re not a huge literary fan, it’s one of the best ways to understand why people fall so hard for Key West.

Hemingway lived in this Spanish Colonial home from 1931 to 1940, during what you’ll learn were his most productive years. The house itself is beautiful, but cat fiends will love all of the six-toed cats that prowl the grounds. 

Fun fact: These are literal descendants of Hemingway’s original feline companion, so be respectful, even if you’re a dog person.

Tours are self-guided, and you can just pop in when you’d like to go. The museum is open daily from 9am to 5pm. Admission used to be cash only, but they’ve gotten with the times and take credit cards now, with a convenience fee. 

Stop 4: The Rum Bar

Reward your sightseeing with a midday pause at The Rum Bar on Duval Street. It’s obviously fun for their curated selection of rum — you can have yourself a little tasting here if you’re a connoisseur — but the people watching is off the chain.

During our cocktail break, we got to share the space with a gentleman in what I can only describe as a dominatrix bunny costume. I’d include the image here, but it’s just not the kind of blog I run. I don’t kink shame, either, but I’d be lying if I said I wasn’t transfixed. 

READ MORE: Interested in bars with a vibe all their own? Check out my honest review of Flora-Bama!

Optional Stop 5: Truman Little White House

If you’re looking to slow the pace a bit, the Truman Little White House is a quiet stop. Once President Harry S. Truman’s winter retreat, it offers a glimpse into Key West’s role in mid-century American history.

You also won’t get the crowds here that gather at the Hemingway property, so it’s a quicker visit. 

The rooms here are modest, and the experience is more about context than spectacle. I’d recommend it as a good fit if you like history told through lived-in spaces, but it’s not as big a must as some of the other stops today.

Stop 6: Fort Zachary Taylor State Park

If you want beach time in Key West, this is where you go.

Fort Zachary Taylor State Park combines history and one of the island’s best swimming spots. The fort itself dates back to the mid-1800s and played roles in both the Civil War and the Spanish-American War, but the beach is the real draw.

There’s white sand, clear water deep enough for actual swimming, and plenty of fish if you bring a snorkel. We enjoyed taking some glamour shots at some of the lookouts here, too. Relax here until it’s time to freshen up for dinner.

Stop 7: Dinner

You can plan your evening around more sunset-themed good times, or embrace those waterfront vibes with some seafood. We enjoyed 7 Fish, a bistro with a comfort food-focused menu of scallops and scampi. 

Hogfish Bar & Grill is more casual, but super popular with the locals. They’re known for their Hogfish Sandwich, a beast of a thing piled high with cheese, onions, and mushrooms. Blue Heaven is another quirky favorite.

For dessert, the cheekily-named Better Than Sex is all indulgent dessert and cocktails. Carrot cake lovers will want the Caress My Carrot.

You’re back at your Key West accommodations for the night. You’re hitting the road again tomorrow, so don’t get too crazy!

Day 4: Key West to Miami

How you approach today depends on how you’re getting back to your final destination. If you just need to make it back to Miami by dark, you can have a slow morning. We had a flight out this day, so we didn’t spend too much time messing around.

In any case, give yourself at least four hours to get back to Miami from Key West. That gives you some buffer time in case there’s traffic. (The drive from Key West to Miami International Airport typically takes between three and four hours.)

Stop 1: Cuban Coffee Queen

For one more Key West legend, stop at a Cuban Coffee Queen on your way out. There are four of them around the city. If you’re hungry, their Cuban breakfast burrito slaps, but they have smoothies, too, if you’re feeling a little sluggish.

Stop 2: History of Diving Museum

I snuck in some more nerdery for you, because that’s how we roll.

The History of Diving Museum traces our relationship with the underwater world, from early free diving and copper helmets to modern deep-sea exploration.

The exhibits are fun and well-paced, and you don’t need to be a diver to appreciate the mix of science, engineering, and sheer obsession on display. It’s also air-conditioned and educational without being heavy.

If I haven’t convinced you, you can make a detour to the Blue Hole, a former quarry turned freshwater pond that’s now part of the National Key Deer Refuge, instead. There’s a short walking loop where you might spot key deer, turtles, and even alligators. 

It’s not the most beautiful spot in the Keys, but it’s generally quiet, uncrowded, and a decent option if you like getting those steps on driving days.

Stop 3: The Fish House

This casual spot is a Key Largo classic. The Fish House is also a market, but if you have the time, sit down for a lunch of any of their fish platters.

Choose between fried, grilled, blackened, broiled, or jerked if you’re feeling saucy. They have both stone crab and lobster when they’re in season. If you haven’t had a smoked fish dip on your trip yet, this one is a great option to try some. 

Optional Stop 4: Biscayne National Park

If you’re really spoiled for time, Biscayne National Park is an underrated gem and not too aggressive a detour on your way to Miami.

Most of the park is water, but the Dante Fascell Visitor Center is nice for shorter visits. From the visitor center, walk along the shoreline for views over Biscayne Bay.

You’ll learn about the park’s mangrove ecosystems and maritime history without getting too strenuous about it. From here, you can wander the jetty, watch the boats drift past, and go bird-spotting if you’re into that. 

If you have closer to two hours, consider booking a short boat tour from the visitor center. These tours head out onto the bay and give you a better sense of how vast the park actually is.

Stop 5: Miami

This is where I leave you. As you leave the park, it becomes more obvious that you’re no longer in the Keys. Miami’s a good time, but it can also be chaotic.

If you’re staying overnight, embrace those Miami vibes with a meal at one of the city’s many true Cuban restaurants.

Puerto Sagua Restaurant is a staple if you don’t mind the roadside vibes. Cafe La Trova is more upscale, with live music most nights for those with the energy.

Just one night in Miami makes the Overseas Highway feel so far away. I know I was feeling nostalgic as soon as we hit the city traffic!

With More Time in the Florida Keys

You can do quite a bit with four days for a road trip through the Florida Keys, but you won’t get bored here with more time.

Here are a few things we have saved for next time:

• Book one of the most popular tours in the region, a Cuban and Caribbean food tour in Key West.
• Visit the Crane Point Museum and Nature Center in Marathon.
• Learn about the region’s martime past at the Florida Keys History & Discovery Center in Islamorada.
• Stop at Indian Key Historic State Park, accessible by kayak, to explore the ruins of a nineteenth-century ghost town.
• See the Fort East Martello Museum & Gardens, a historic site in Key West.
• Have someone else take over the planning on an Old Town Trolley tour of Key West.
• See the critters at the Dolphin Research Center, one of the most popular things to do in Grassy Key.
• Take a sunset cruise in Key West, complete with open bar.

The Florida Keys show off the best of Florida.

This is the version that feels unhurried, a little weird, and refreshingly unconcerned with doing things the “right” way.

A road trip exploring the Florida Keys is perfect for anyone who loves to embrace the detour. You won’t be putting too many miles on your car, but that’s really not the point.

If nothing else, you’ll come away with proof that sometimesthe best trips are held together by one very scenic road.

Planning travel in the Southeast? Check out these guides:

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• Spend the Best Day in Savannah
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More stops to make on a Southeast road trip:

• Our Favorite Day Trips From New Orleans
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• A Date Guide to Savannah, Georgia
• How to Plan a Visit to Hot Springs
• A Date Guide to New Orleans

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