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Miami to Key West: Insider Tips to the Perfect Florida Keys Road Trip Itinerary

by Roslie

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Who says that you have to travel far from home for an exotic beach escape? Swim in turquoise seas, lounge on white-sand beaches, and taste your way through ultra-fresh exotic local dishes. From Miami to Key West, there is a world to explore in those magical 160 miles from the city down through the keys.

What does one do when your domestic and international travel plans have been canceled due to a pandemic? After a few months of being cooped up indoors, my COVID bubble and I needed a slight change of scenery. So, we planned an impromptu Florida Keys road trip, slowly traversing through the islands and savoring the Keys vibe that kept us busy for a few days.

Ready for the ultimate tropical escape? Here is your dream Florida Keys road trip itinerary.


Please keep in mind these details are subject to change. Due to COVID-19, social distancing and face coverings may be required. Be sure to check local health officials’ safety regulations and each establishment’s website for updated information before making final plans.

This post contains affiliate links, meaning if you buy something through one of these links, I may earn a small commission, at no extra cost to you. Please read my full disclosure policy for more information.


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How Much Time to Plan for a Florida Keys Road Trip Itinerary

I get many questions from you guys about planning a Florida Keys road trip. The most common question of all is: how much time do I need for a road trip in the Florida Keys? For me, the more, the merrier!

Key West Florida U.S. Route 1 or Highway 1

Life moves slower down here. A trip to the Florida Keys isn’t about jamming as much as you possibly can into a short time. It’s a bit lingering in the moment and soaking in the natural beauty.

While you could do the drive in one day, it frankly would not be worth it. What is a trip through the Florida Keys without taking in at least one sunset? Embrace the laid-back Keys lifestyle by giving yourself at least three days to explore all of the best of the islands.

If you are the kind of traveler looking to see the Florida Keys off the beaten path, plan for a solid five days. Just don’t leave home without a copy of the Insider’s Guide to the Florida Keys & Key West.

If you’re on a time crunch, though, and need to get home at some stage, at least give yourself one overnight stay in the Keys.

What Should I Pack for a Florida Keys Road Trip?

When planning what to bring on your South Florida getaway, the usual suspects should make an appearance on your road trip packing list: sunscreen with at least 30 SPF, sunglasses, a towel, and any wide-brimmed sun hat.

Beach accessories sun hat and sunglasses

One or more bathing suits are beach essentials, and ladies might feel more comfortable bringing a wrap or beach cover-up (like these) for use while shopping or dining.

Casual clothing is the order of the day just about everywhere, but if you want to experience nightlife especially in South Beach, bringing some fine attire will help get you through the door. 

What is the Best Time of Year to Visit the Florida Keys?

One of the best things about Florida is that you will have incredible year-round weather. Whether it’s getting active and exploring the cultural sites during the “cooler months” or soaking in the scorching summer sun, you can always find the perfect thing to do 365 days per year in Florida.

That said, if you want an insider trick, finding the best time to visit the Florida Keys is all about matching the season with your travel style.

While some people love a high-energy adventure with activities galore, others want nothing more than to get away from the world and sip a cocktail from a coconut. The good news is that you can do both here. You just need to plan ahead.

Find your perfect Florida Keys outdoor adventure


When is Peak Tourist Season in the Florida Keys?

The most popular time of year to visit the Florida Keys is during winter, from Christmas time until the middle of April. People from all over the U.S., Canada, and beyond are all hitting the country’s southern edge looking for that elusive summer sun.

Tiki Bar Postcard Inn, Islamorada, Florida

Want to spend your Christmas break with afternoon temperatures pushing 80 degrees? You can do it right here. Do be prepared to pay the highest prices of the year and, for better or worse, come during the very busiest time of year.

When is the Cheapest Time to Visit the Florida Keys?

While it is not the cheapest place in Florida to visit, you can plan an affordable trip to the Keys with a few tricks. You will generally find the best rates during the off-season, which runs from June to November.

In September, as kids are heading back to school and again in November as families start to gear up for the holidays are typically the very cheapest times to visit the Florida Keys.

Florida Keys Beach

Local Tip: As you plan the best times to visit the Keys, do note the official hurricane season runs from the start of June until the end of November. While a hurricane is always possible in those months, the season is most active from mid-August until September.

If you are considering this period, do check your hotel’s hurricane policy. Most will have the required safety measures in place, offer a refund if your trip is affected. Also, note that severe hurricanes are not a yearly occurrence (check the stats to put your mind at ease).

The Very Best Time to Visit the Florida Keys

Personally, my favorite time of year to visit the Keys is the time that travel experts call the “shoulder season.” This is the time just before and just after summer. It is when you get perfect not-too-hot weather and narrowly avoid the masses of families trying to get in a summer break before going back to school.

Visit from late April to early June and then again from November through mid-December; you will find perfect weather, virtually no chance of a hurricane, and reasonable prices.

Feeling inspired? Now check out my Florida road trip essentials for the final step you’ve got to take before you hit the road.

The Best Events of the Florida Keys

On top of looking at hotel pricing and the weather, it is well worth checking out an event calendar for the Florida Keys. This area has so many amazing, quirky, and wholly unforgettable festivals all year-round.

Before you go, be sure to check out the official Keys event calendar.

Key Largo & Islamorada Food and Wine Festival
Key Largo & Islamorada Food and Wine Festival

Foodies will love events like January’s Key Largo and Islamorada Food & Wine Festival, as well as the Key West Food & Wine Festival or the Original Marathon Seafood Festival in March.

Water lovers will head over flippers for the Lower Keys Underwater Music Festival in July, January’s Quantum Key West Race Week, or November’s Super Boat World Championship.

Movie Buff? It’s all about Humphrey Bogart Film Festival in October — and that is just to name a few options!

Miami to Key West Drive Road Trip Stops

Now that you’ve started to get an idea of when to visit the Florida Keys let’s talk about location. Assuming you’re not lucky to spend a lifetime in the Keys, you will have to prioritize.

With so many drop-dead gorgeous waterfront views and fascinating roadside attractions, planning the perfect Florida Keys road trip itinerary can be tricky.

After countless road trips in the Florida Keys, I still can’t choose my favorite spot! There are so many incredible places that you’ll have to decide for yourself which is the very best.


Discover local markets, eateries, historic landmarks, and more, all at your own pace. Download the Overseas Highway self-driving guide as a companion to your Florida Keys road trip itinerary.


The Perfect Florida Road Trip: It All Begins in Miami

Miami is a perfect place to start your Florida Keys road trip. Not only are there endless bucket list things to do in Miami, but it is also an excellent base because it is the closest airport to the upper Florida Keys.

South Beach, Florida, Ocean Drive

While you can fly into Key West International Airport, you will often pay a premium. You will find cheap flights to Miami from all over the world, so you won’t want to miss out.

If you can, I would highly recommend spending at least 24 hours in Miami to see the best of the best.

Your First Day Trip from Miami: Homestead

Whether you are looking for a day trip from Miami or looking for the first stop in your Florida Keys road trip itinerary, plan some time to visit Homestead.

Just 30 miles outside of Miami, beside the Everglades National Park, it is a fun little town packed with family-owned businesses.

Robert Is Here Milkshakes and Smoothies Stand

Even if you only make a quick pitstop, get to Robert is Here. Sample a dizzying array of exotic fruits and vegetables, or bite into the latest harvest straight from their farm. It is the perfect spot to load up the car with road trip snacks. 

Foodie Alert: Whatever you do, don’t leave here without getting a shake for the road. There are varying flavors with the mango passion fruit combination being one of my faves (you can thank me later!).

Starting Your Florida Keys Road Trip with Key Largo

Driving south on U.S. 1, for about 20 miles from Florida City, passing marshes, lagoons, and finally crossing azure waters, you’ll arrive at Key Largo. One of the Florida Keys highlights and the perfect place for your first overnight stay.

Alternately, you can detour from US 1 at mile marker 126.5 to approach Key Largo from the north, which would allow for a stop at Alabama Jacks, where you can enjoy conch fritters and sea breezes in a typical Florida Keys roadside establishment that sets the tone for the rest of your trip.

What to Do in Key Largo

Perhaps best known as the Dive Capital of the World, you can get your feet wet at the world’s largest artificial reef then explore the incredible John Pennekamp Coral Reef State Park (MM 102.6).

If you are diving here, be sure to bring your underwater camera for a selfie with “Christ of the Abyss,” a 9-foot-tall coral-encrusted bronze statue of Jesus and one of the world’s most iconic underwater sights.

This one of my all-time favorites things to do in Key Largo, whether on a road trip through the Florida Keys or just a day trip from Miami.

Where to Eat in Key Largo

You’d do well to stop at Key Largo Chocolates (MM 100.5) to sample some topnotch sweets. And I am not just talking chocolate. You’ll find handmade cakes, pies, and ice cream in every flavor of the rainbow.

Key Largo Chocolates Cakes & Ice Cream

I can’t stop here without picking up a few truffle pieces. I highly recommend strawberry, coconut, and mango flavors (so maybe save room for three desserts).

Key Largo Fisheries Fish Dip

If you’re even remotely hungry, you’ll want to stop at Key Largo Fisheries at mile marker 99.4 — the best seafood market in the Florida Keys for the smoked fish dip. The conch fritters are well worth a try too!

Mrs Mac's Kitchen Hogfish Wrap

Also nearby is the oldest restaurant in town: Mrs. Mac’s Kitchen (MM 99.3), with a Hogfish wrap that is not to be missed.

Where to Stay in Key Largo

When it comes to lay your head in paradise, here are a few favorite spots:

  • Hampton Inn Key Largo: You can often find deals for around $100 per night at this cozy pet-friendly spot.
  • Holiday Inn Key Largo: For only around $20 more, you can hang your hat at Tiki Bar and splash around in the waterfall at this reliably nice spot.
  • Atlantic Bay Resort: A mid-priced spot (more expensive than the Holiday Inn or Hampton Inn, but a bit less than Baker’s Cay), it is all about the picture-perfect private beach here.
Search more top-rated Key Largo hotels and accommodations here.

Pit Stop: Tavernier

As you are traveling from Key Largo to Islamorada, stop in Tavernier, the next key on the chain (pun intended), where you will find the Florida Keys Wild Bird Center at MM 92.

This bird rehab center is free to the public (though donations are appreciated) and well worth the 15-20 minutes it takes to walk the boardwalk and observe the pelicans, egrets, herons, and other injured birds being housed by volunteers.

And while on Tavernier, I recommend a visit to the Blond Giraffe Key Lime Pie Factory (MM 92.2) for a sampling of what else than the world-famous key lime pie?

One of the Best Places to Stay in the Florida Keys: Islamorada

People often ask me, which is better: Islamorada or Key Largo? To that, I say, why not both? While Key Largo is a diving mecca, Islamorada is the Sportfishing Capital of the World.

What to See and Do in Islamorada

Moving along the island chain, it is time to soak in some culture at the Rain Barrel Artisan Village (MM 86.7). This arts and crafts village is a prime spot to find that one-of-a-kind souvenir to remember your Florida Keys road trip.

Betsy the Lobster, Rain Barrel Village, Islamorada, Florida

Pro Tip: Be sure to bring your camera to the Rain Barrel Artisan Village. Even if you aren’t inclined to buy any of the handiwork, you should at least get a picture with Betsy—the giant lobster sculpture sitting right out front makes for a great selfie.

Theater of the Sea, Islamorada, Florida

Just a few minutes down the road, you will find Theatre of the Sea (MM 84.2), the world’s second-oldest marine mammal attraction, which hails back to 1946. Here’s your chance to see shows featuring dolphins and sea lions, and even get the opportunity to swim with them. Theatre of the Sea is an especially fun stop if you’ve got kids.

For a different kind of animal interaction, be sure to get over to Robbie’s Marina (MM 77.5) to feed the tarpons. Admission to the dock is $2.25 per, and for another $4 you can grab a bucket of fish to toss to the tarpons gathered around.

Robbie's Marina Islamorada, Florida

At 5-8 feet in length and up to 150 pounds, these are no mere goldfish, and at less than ten bucks, it’s a cheap and unique thing to do on your Florida Keys road trip.

Once you’ve taken care of the tarps and ready to unwind, get to Anne’s Beach (MM 73.4). One of the best beaches in the Florida Keys, you need at least a couple of hours here to enjoy the shallow waters.

Planning Tip: Before you go, be sure to check out my complete list of beach essentials. As any Floridan knows, you will spend a fortune buying the basics from beachside stores. There are a few things you’ve just got to bring with you to make the most of your cash and time.

Where to Eat and Drink in Islamorada

Of course, when you are in the fishing capital of the world, you’ve got to get your fill of seafood! For that, get over to the famous Whale Harbor Seafood Buffet (MM 83.4) and eat until your heart’s content.

Once you have had a taste of the high seas, head over to the Postcard Inn Beach Resort & Marina (MM 84.1)—formerly known as the Holiday Isle Tiki Bar — don’t come thirsty, though. Famous for their rum runner, I find the drink sickly sweet and overpriced.

That said, it will cool you down on a hot day, and is well worth the trip for the fantastic views (and selfie ops) from their expansive deck, remodeled after the destruction left by Hurricane Irma.

If you’re a craft beer lover, head over to taste the local brew at the Islamorada Brewery & Distillery (MM 82.2). Fill up on craft beers in this local brewery taproom, then continue to the Florida Keys Brewing Company (MM 82.1).

This local craft brewery has a stunning backyard beer garden, complete with regular live musical acts. Thanks, Chef Kirk, for bringing this charming gem to my attention.

Morada Bay, Islamorada, Florida Keys

For live entertainment, along with a beautiful waterfront dining room and a very Florida Keys vibe, it’s all about Morada Bay.

Fun Fact: The Netflix Series Bloodline was filmed right in Morada Bay in Islamorada.

Either way, that Caribbean vibe is ever-present and whether drinking or dining, and I’d highly recommend planning a night in Islamorada.

Where to Stay in Islamorada

With all of the fabulous nightlife in Islamorada, you will definitely need a place where you can get some R&R. Here are a few spots I love:

Find a great place to stay in Islamorada! Read reviews, check rates, and availability here!

Family-Friendly Florida Keys Road Trip: A Stop in Marathon

Planning Tip: Up to this point (and after), addresses are tracked by mile marker; Marathon Key, however, goes by a numbered cross street system. But for our intents and purposes, I’ll list the mile marker to keep it consistent.

Florida Keys Overseas Highway

Right in the middle of your road trip in the Florida Keys, you will find Marathon. Spread out over Grassy Key, Vaca Key, and Fat Deer Key, this is a family vacation favorite (though it’s a bucket list destination for anyone and everyone).

Whether you are 8 or 80, you will love the Dolphin Research Center on Grassy Key (MM 58.9). Swim with the dolphin and learn about the lives of these famous locals. Next up, all of you animal lovers will want to make a beeline for the Turtle Hospital (MM 48.5). An education spot with a very worthwhile cause.

Once you have learned a new appreciation for the seas, get over to another one of the best beaches in the Florida Keys. You’re not going to want to miss the quaint tropical wonderland that is Sombrero Beach on MM 50.

With plenty of parking and refurbished after Hurricane Irma in 2017, this is another chance to catch some rays while reclining on beautifully soft sand.

Where to Eat in Marathon

Just before the Seven Mile Bridge, between mile markers 48 and 47 there are two wonderfully situated eateries that both deserve a visit.

First, it’s all about Burdines Waterfront (MM 48), which requires a detour off the main road down East 15th Street. Before you go, charge your phone, then rely on your GPS to get to this spot because it can be a bit tricky to find.

Burdines Waterfront Restaurant Key Lime Pie

Follow your GPS for a payoff that includes fabulous views from their upstairs terrace as well as this unconventional (and crazy delicious) fried key lime pie that is an absolute MUST.

It’s more like a key lime pie turnover, but one of the best treats on our Florida Keys road trip.

Just down the road is the aptly-named Sunset Bar and Grille, located at the base of the famous Seven Mile Bridge.

Sunset Sunset Grille & Raw Bar Marathon, Florida Keys & Raw Bar Marathon

While the views are always fantastic, I strongly suggest that you try to arrive here around sunset for an unbeatable panorama combining sea breezes, natural beauty, and a heavy dose of Florida Keys culture.

Where to Stay in Marathon

Literally in the middle of all the best of the Florida Keys, Marathon is an ideal spot for an overnight stay. Here are two that are always good:

  • Banana Bay Resort & Marina: For a dream stay in a picture-perfect marina, this hotel is a great mid-priced pick.
  • Tranquility Bay Resort: This award-winning four-star resort is a destination in and of itself.

Find your perfect place to stay in Marathon: read reviews, check rates, and availability here!

Exploring the Lower Keys

Though technically just 6.8 miles long, the longest span in the Keys, the Seven Mile Bridge is where the term ‘epic road trip’ will come to mind as you gaze over the blue waters spreading out in all directions while traveling on a narrow ribbon of asphalt.

Florida Keys Seven Mile Bridge

Once across the bridge, you’re in the home stretch towards Key West, and when it comes to places to explore in the Lower Keys, you will be spoiled for choice.

A Stop in Bahia Honda Key

One of the best beaches in the Florida Keys, I adore the Bahia Honda Key State Park (MM 36.8 – 38.5). Bring your beach gear, and make sure you’ve got your camera to snap picks of the iconic crumbling old railroad bridge.

Exploring Big Pine Key

Another must-visit for animal lovers is Big Pine Key. This spot is especially cool because it is home to the endangered Key Deer, which is found exclusively in the lower Florida Keys.

Key Deer Big Pine Key, Florida

While you do have to drive around for a while to find them, we spotted two little ones on our drive.

Key Deer in Big Pine Key

And, thanks to our resident zoo expert, Terry, we have these snaps. He was a little more adventurous than I at attempts to capture pics of these little creatures.

A visitor center (MM 30.3) is open on US 1, but if you’d like to educate yourself before arriving, you can learn more at National Key Deer Refuge.

Blue Hole Big Pine Key

Once you have found your deer, swing by the Blue Hole. Also, part of the National Key Deer Refuge, the Blue Hole is the largest freshwater pond in the Florida Keys and a wildlife sanctuary for birds, snakes, and alligators in addition to the Key Deer.

Helpful Tip: Keep an eye on your speedometer—Big Pine Key’s speed limits are strictly enforced. If you are on local roads, it’s 30 mph. If you are on the highway, it’s 45 mph during daylight hours and 35 mph after dark.

Where to Eat in Big Pine

Whether you’re hungry or not, I suggest a stop at No Name Pub for lunch, dinner, or a drink. Covered in autographed dollar bills, the history in this colorful spot goes back to the 1930s.

This charming spot has been home to everything from a general store to a brothel to now serving mouthwatering conch fritters with excellent service.

Be sure to stop by and say hello to Christine, the best waitress of the trip!

Eating in Stock Island Key

Want to experience the local Keys culture? For a great ambiance and local vibe, swing by the Hogfish Bar & Grill as you continue your Florida Keys road trip down to Key West.

Arriving in Key West

For the next 30 miles, you’ll make your way through several smaller Keys, until you arrive at the Southernmost city in the U.S.A. — Key West.

There are so many things to do in Key West you would be remiss if you didn’t budget some time to stay at least overnight and sample a few. I’ve got a whole post dedicated to just that— a day in Key West.

Continue your journey here with our A Day in Key West Itinerary

Key West Neighborhood

If you are in a rush, though, note that you’ve got to explore Duval Street, then take the Old Town Trolley Tour or Conch Train tour to get the lay of the land.

Visit the Key West’s iconic sites, and Dry Tortugas National Park then hit the beach for parasailing, snorkeling, and sunset cruises. Here are some more options for exploring Key West.

Where to Stay in Key West

  • Santa Maria Suites Resort: I love this place for the condo-style suites with a kitchen. If you are saying a couple of nights, this is a major perk.
  • The Reach Key West: Proudly home to the only private natural-sand beach in Key West, this stylish spot has it.
To see a full list of Key West accommodations, click here.

Recap

Whether you spend a long weekend or a week exploring the route from Miami to Key West, there is always more to see. While it is excellent to start with a Florida Keys road trip itinerary with all of the key spots (couldn’t resist that pun!), the best adventures are often unplanned.

From the moment you cross over into the Keys, enter the next address into your GPS, then let your mind wander. Let your curiosity guide you off the beaten path to a tucked-away beach or a hole-in-the-wall cafe.

Take your time exploring. After all, the very best thing about the Florida Keys is the laidback beach-loving way of life.

Feeling inspired? See how many adventures you can check off this classic Florida Keys road trip bucket list.

Map: Florida Keys Road Trip itinerary

Save this map to your phone and use it to plan your Florida Keys road trip itinerary.

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