Best 5 Day Florida Keys Road Trip Itinerary: Map of keys Florida Guide

Last updated on December 23rd, 2024 at 09:01 pm

Are you looking for the perfect Florida Keys itinerary guide? We’ve Created the Best 5-Day Florida Keys Road Trip Itinerary, filled with adventure tips, must-see spots, and local favorites. Plan your unforgettable trip now!

The Florida Keys is America’s ultimate coastal paradise, where emerald-turquoise waters meet endless blue skies. It is the perfect American vacation, with palm trees swaying in the breeze, sherbet sunsets, colorful architecture, and beachfront bars serving cold drinks in the Florida sun. It’s the only tropical getaway in the US.

We’ve highlighted our adventures to create this 5-day Florida Keys road trip guide from Miami to Key West. Consider this your flexible itinerary. We’ve included our favorites and must-sees, but you can customize this trip to fit your interests and travel style.

The Perfect Guide 5 Day Florida Keys Road Trip Itinerary

🗺 5 Day Florida Keys Itinerary Map

Here or Below to see our 5-day Florida Key itinerary on Google Maps. Florida Key is a small cluster of islands located south of Florida. It takes about two hours to reach Key West from Key Largo and around 1  2h 15m (68 km) to Miami.

Florida Keys Road Trip Mile Markers

The idea of using mile markers as addresses actually originated with the Florida East Coast Railway, built by Henry Flagler in the early 1900s. When the devastating Labor Day Hurricane of 1935 destroyed much of the railroad (known as the “Railroad That Went to Sea“), the state purchased the remaining infrastructure and converted it into the Overseas Highway, essentially building the road on top of the old railroad bed.

The mile marker system proved so practical that it was retained, creating this unique addressing method, which is still used today.

Each address in the Keys corresponds to its distance from Mile Marker 0 in Key West, making it remarkably easy to gauge distances. The markers start at around MM 127.5 in Florida City (mainland) and count down to Key West.

It’s a wonderfully logical system. If someone tells you they’re at MM 80 and you’re at MM 90, you know exactly how far you need to drive (10 miles). This is particularly helpful because the Keys are essentially a single-road community strung along US-1.

When’s the best time to visit the Florida Keys

The best time to visit the Florida Keys is during the winter months. This is the most popular season because the weather is comfortable, and visitors can escape their cold-weather homes to enjoy one of the best warm winter destinations in the USA.

Spring is also an excellent time to visit the Florida Keys. You can enjoy the islands before the temperatures become too hot and humid, and you’ll benefit from smaller crowds and lower room rates compared to the peak winter season.

Remember that hurricane season runs between June and November, so traveling during these months is a gamble.

How far is it from Miami to Key West?

The distance between Key West and Miami Airport was approximately 150 miles, with the road being 225 km long. Key West is located between Key Largo and Key West at 106 miles.

The Best 5 Day Florida Keys Itinerary for First Timers

If you’ve ever wondered what it would feel like to hop from one tropical island to another without leaving the U.S., look no further than the Florida Keys Itinerary.

Warm sunshine, turquoise waters, swaying palms, and a relaxed island vibe await you here. Strap in as we uncover what makes this 113-mile string of islands truly unforgettable!

Overview of the Florida Keys

You’re cruising over 42 bridges, with the Atlantic Ocean on one side, the Gulf of Mexico on the other, and the open road in front of you. That’s the magic of the Overseas Highway, which connects the Florida Keys.

Of these islands, more than 800 of them, though most are uninhabited, stretch from the tip of mainland Florida down to the vibrant city of Key West. Driving them from end to end can take around 3 hours.

To make planning easier, the Keys are generally divided into:

1. Upper Keys (closest to the mainland)
2. Middle Keys
3. Lower Keys (including Key West)

In this 5 Florida day itinerary, you’ll experience a little bit of everything, from the laid-back Key Largo to the funky, artsy Key West.

How to Get to the Florida Keys

Flying into the Keys

Key West International Airport (EYW) is the one major airport in the Keys, located right on Key West itself. It’s charmingly small, which means you can start your island fun within minutes of landing. However, the downside is often higher ticket prices and limited flight routes.

Alternatively, many travelers prefer to land at either:

• Miami International Airport (MIA)
• Fort Lauderdale-Hollywood International Airport (FLL)

Both are well-served by major airlines, so you can often score cheaper flights and find more flexible travel times. From Miami, it’s about an hour’s drive to Key Largo. Fort Lauderdale is a bit farther, roughly 1.5 hours away. Continue to your best five Florida Keys itinerary.

A Few Extra Travel Tips

• Car Rentals: If you fly into Miami or Fort Lauderdale, renting a car is almost always the best option. The drive along the Overseas Highway is one of the most scenic in the country, so you’ll want your own wheels to make spontaneous beach stops.
• Toll Roads: Florida has a few toll roads. Make sure your rental car has a SunPass (or similar toll pass) so you won’t have to pay cash at every booth.

Now that you know how to touch down in this little slice of paradise, you’re ready for the 5 Day Florida Keys Itinerary for First Timers. Get ready to experience the island life at its finest breezy sunsets, tropical cocktails, eclectic local eats, and memories that’ll have you dreaming about your next Keys adventure before you even leave. Bon voyage!

Things to Know Before Visiting the Florida Keys

Plan Your Dream Keys Adventure: Miami to Key West

Before you start your adventure through the 5 Day Florida Keys Itinerary, here’s your ultimate guide to making the most of this tropical paradise. The Keys offer an incredible array of experiences, from natural wonders to cultural hotspots, ensuring your Florida road trip is unforgettable.

Here are some extra tips :

Renting a Car For Your Florida Keys Drive

Wherever you fly in, you’ll want a rental car to fully enjoy this route. The Florida Keys cover more than 100 miles, so if you plan on exploring everything from Key Largo to Key West, having your own vehicle is essential.

You must plan ahead when renting a car from Key West International Airport (EYW). Accessing the rental car facility is easy and painless.

After you pick up your luggage, look for the signs for the MIA Mover shuttle service, which will take you directly to the rental car center.

Before you agree to the rental insurance, contact your credit card company to see if auto rental is included in your card benefits.

If your credit card includes rental coverage, ask if you need documentation from your card issuer to confirm this coverage so you don’t get redundant coverage when you pick up the car.

Some companies now require proof of credit card insurance, which can be obtained by calling your card company quickly. However, you must do it before you travel.

Other Parts of Florida

For in-state travelers who enjoy hitting the open road, driving from other parts of Florida to the Keys is a great way to experience this tropical paradise.

Below are the approximate driving times to Key Largo from several major Florida cities:

• Miami to Key Largo: ~1 hour
• Orlando to Key Largo: ~4 hours
• Tampa to Key Largo: ~5 hours

Day 1: Arrive in the Florida Keys

Alright, let’s kick off your 5-day Florida Keys adventure! First stop: the Upper Keys imagine clear-as-glass waters and an easygoing pace (a big contrast to the hustle of Key West).

Whether you fly into Fort Lauderdale (FLL) or Miami (MIA), you’ll head south on either the Florida Turnpike or I-95. Once you reach Florida City, hop onto “The Stretch,” an 18-mile portion of US1 leading right into Key Largo.

Cross the Jewfish Creek Bridge, and welcome to Key Largo! It’s the largest of the Florida Keys and home to John Pennekamp Coral Reef State Park, the very first undersea park in the U.S.

For this itinerary, you’ll actually be staying in nearby Islamorada instead of Key Largo. But if anything in Key Largo catches your eye, feel free to pull over and explore; it’s all part of the adventure.

Cabana Bar is another beloved spot in Islamorada. Keep an eye out for the giant mermaid statue marking the entrance; you can’t miss it! Situated right on the bayside, Lorelei’s offers unbeatable sunset vistas, live music, and some of the freshest seafood you’ll find.

Start off with their famous fish dip and a brightly colored tropical cocktail, then stick around to watch the sun slip below the horizon. It’s easily one of the top places in the Keys to catch a truly spectacular sunset!

Afternoon: Arriving in Islamorada

Welcome to your little slice of paradise! A mere 30-minute drive south of Key Largo lands you in Islamorada, a vibrant village that I’d pick again and again for its stellar restaurants, laid-back breweries, and endless activities. While you could stay in Key Largo, Islamorada just has a certain magic, from incredible seafood to unforgettable sunsets.

Check-In & Lunch

If you arrive early and your stomach’s rumbling, head to the legendary Tiki Bar at Postcard Inn Beach Resort & Marina (now Three Waters). This beachfront spot is famous for inventing the Rum Runner, a fruity cocktail that screams, and you’ll be living your best Keys life right off the bat.

Evening: Sunset Dinner at Lorelei’s

As dusk approaches, make your way to Lorelei’s Restaurant & Cabana Bar, which is easily one of the best places in Islamorada to catch the sunset if you look for the giant mermaid on the side of the road.

Why Lorelei’s Rocks

Situated on the bayside, Lorelei’s offers front-row seats to some of the most spectacular sunsets in all of the Keys; dig into their famous fish dip and let the live music lull you into ultimate relaxation.

When the sun begins its evening show, you’ll see why this spot is a local legend. There’s nothing quite like the sky turning brilliant shades of orange, pink, and purple over the water.

Where to Stay in Islamorada

If you’ve been wondering where to stay in Islamorada, you’ll be happy to know this dreamy Florida Keys hideaway is brimming with options, from cozy beach bungalows to luxe resorts with all the extras.

Here are a few of our top picks:

1. Cheeca Lodge & Spa
   If upscale comfort is what you’re after, look no further than Cheeca Lodge & Spa. With its beachfront rooms, nine-hole golf course, and a full range of amenities for both couples and families, this resort is as luxurious as it is welcoming.
2. Islander Resort
   For a relaxed, family-friendly getaway, Islander Resort is the perfect choice. It offers direct beach access, comfy rooms, multiple pools, and plenty of on-site fun, making it the perfect base for exploring Islamorada’s laid-back charm.
3. The Caribbean Resort
   Boasting 22 distinct, a small marina, and a picturesque zero-entry pool, The Caribbean Resort is ideal for large groups or anyone craving a bit more space.
4. The Moorings Village
   If privacy and romance top your list, The Moorings Village will sweep you off your feet.

Whichever spot you choose, Islamorada’s laid-back atmosphere and pristine scenery promise an unforgettable stay in the heart of the Florida Keys.

Day 2: Snorkeling and a Sunset Dinner

Morning: Snorkel Adventure

Start your day with a light breakfast at your hotel, or make a pit stop at Midway Cafe in Islamorada for scrumptious pastries and coffee (a rarity in the Keys!).

Once you’re fueled up, it’s time to experience one of the Florida Keys’ biggest highlights: snorkeling. The Florida Keys National Marine Sanctuary is home to the only barrier reef in North America, so you’re in for a treat!

While there are many snorkel tour options in Islamorada, we recommend picking one that visits Alligator Reef or Cheeca Rocks (weather permitting). It’s the Sundance Watersports World Famous tour, and it’s a perfect option. The waters around Alligator Reef are absolutely unreal, and you’ll spot tons of marine life by the lighthouse.

If you’re eager to see the famous Christ of the Abyss statue, you’ll need to head north to Key Largo. It’s located in John Pennekamp Coral Reef State Park, one of the most iconic spots in the Keys for snorkeling.

And don’t forget about the lively Islamorada Sandbar. Thanks to its shallow waters, boats can anchor right on the sandbar, so you can spend the day hanging out in the sun, sipping drinks, and taking in that laid-back Florida Keys vibe.

Afternoon: Lunch & Local Brews

After an exciting morning in the water, recharge at Shrimp Shack in Islamorada. This casual eatery may not be fancy, but it’s known for dishing up some of the freshest shrimp around—so fresh that it even snagged a feature on Diners, Drive-Ins, and Dives!

Once you’ve satisfied your seafood cravings, head over to Islamorada Brewing & Distillery for an afternoon sampling session. You’ll find a range of house-made craft beers, including the ever-popular Sandbar Sunday, an ideal pick for the island sunshine. If cocktails are more your style, you can sip on rum or vodka concoctions crafted with spirits distilled right on-site.

Be sure to enjoy their relaxed outdoor beer garden, complete with a food truck, lawn games, and plenty of space for both kids and dogs. It’s the perfect hangout for a laid-back Keys afternoon!

Evening: Dinner with a View

As you wiggle your toes in the warm beach, indulge in Caribbean-inspired favorites like grilled yellowtail or Cuban-style pork. With prime views of the bayside, you won’t find a better backdrop for those gorgeous evening hues.

For a more upscale experience, wander next door to its sister establishment, Pierre’s Restaurant, nestled in a colonial-style home. You’ll discover a sophisticated French fusion menu, a beautifully decorated interior, and a breezy balcony perfect for savoring the ambiance and, of course, another incredible sunset.

Day 3: Kayaking, the Tarpon, and from Marathon to Key West

Rise and shine! This is a big day, so you’ll want to get an early start! First up is Mangrove Mike’s Cafe in Islamorada, known for its warm, friendly vibe and hefty portions.

From there, head straight to the iconic Robbie’s of Islamorada, one of the famous spots in the Keys. People flock here to feed the tarpon, and it’s an absolute must-do. For just a few dollars, you’ll get a bucket of fish to dangle over the dock, and this massive tarpon will leap right out of the water, so keep your camera ready!

Robbie’s is perched between Indian Key and Lignumvitae Key, making it the ideal launch point for a kayaking adventure. 

You can rent kayaks on your own or book a guided tour. If you’re new to the area or want some local insight on wildlife and hidden gems, go for the tour. The mangroves and calm bay waters are a dream for beginners and seasoned paddlers alike. 

Afternoon: the Lower Keys Within the Middle Keys

After a fun morning in Islamorada, hop back in the car and head south toward the Lower Keys. While the trip from Islamorada to Key West typically takes under two hours, we highly recommend making it more of an adventure by stopping at a few great spots along the way.

Marathon & The Turtle Hospital

Make your first stop in Marathon to visit The Turtle Hospital, a non-profit dedicated to rescuing and rehabilitating injured sea turtles. Their guided tours offer a rare glimpse behind the scenes, showing how they care for these incredible creatures as they recover.

Seven Mile Bridge

After you leave Marathon, you’ll arrive at the famous Seven Mile Bridge, which, fun fact, is actually two bridges! The older one was originally part of Henry Flagler’s Florida East Coast Railway and was later turned into a highway in the 1930s. In 1982, a new bridge was constructed right next to it.

Portions of the old bridge are still standing, and it has become a favorite spot for fishing and biking. It’s definitely worth stopping for a stroll to soak up the panoramic ocean views.

Bahia Honda State Park

at Bahia Honda State Park. Known for its untouched natural beaches, which are arguably some of the prettiest in the Keys, this spot charges a small entrance fee, but it’s absolutely worth it. You can swim, walk the shoreline, and enjoy impressive views of what remains of the old railway, all while stretching your legs and getting some fresh sea air.

Finally, wave goodbye to Marathon and continue your journey toward Key West. It’s a scenic drive that’ll cap off an epic day of kayaking, tarpon-feeding, and unforgettable Florida Keys fun! Safe travels!

Day 4: Old Town and Beaches

Morning: Old Town Key West

Rise and shine in the heart of Key West, where history and island charm seamlessly blend. Kick off your day at Blue Heaven, a local legend brimming with character through colorful walls,

Stroll through the winding streets of Old Town and discover its iconic treasures:

Southernmost Point Buoy: It’s practically a rite of passage to snap a photo here at the continental USA’s southernmost landmark.

Harry S. Truman Little White House: Step back in time to President Truman’s tropical hideaway.

Ernest Hemingway Home & Museum: Wander through the famous author’s old stomping grounds and say hello to the six-toed cats.

Key West Aquarium: Small but mighty, this charming aquarium offers an up-close peek at local sea life. It’s perfect if you’re traveling with curious kids or love marine wonders.

Afternoon: Lunch and Beach Time

Treat yourself to lunch at one of Key West’s most legendary oceanfront restaurants, with picture-perfect views, a chill vibe, and an upscale menu brimming with fresh, local ingredients. Take your time savoring every bite while that ocean breeze does its thing.

Afterward, make a beeline for Smathers Beach, one of the only spots in the Keys with a seriously wide stretch of white sand. Sink your toes in, swim in the calm waters, or just relax and soak up that famous Florida sunshine.

If you want a bit of history with your beach day, head to Fort Zachary Taylor State Park. Spread over 54 acres at the southern tip of Key West, this park boasts gorgeous blue waters and some of the best walk-in snorkeling around.

Evening: Sunset Cruise

The best way to end your day with a sunset cruise, easily one of the perfect ways to enjoy Key West in all; multiple companies offer sunset sailing tours that cruise around the island, giving you a front-row seat to the fiery colors of the sky as the sun dips below the horizon.

Most cruises come with drinks and snacks, and some even have live music or dancing. It’s the perfect way to celebrate another magical day in paradise.

Day 5: Water Adventures & a Sunset Farewell

It’s the final day of your Florida Keys adventure, and there’s no better way to wrap things up than diving into the clear blue waters by day and soaking in a spectacular sunset by night. Whether you opt for a thrilling Jet ski island tour around Key West or venture 70 miles west to the remote Dry Tortugas, you’re in for an epic finale.

Jet Skiing or Exploring Dry Tortugas

All-Day Adventure

Hop on a ferry or seaplane to Dry Tortugas National Park, a cluster of islands home to Fort Jefferson, a Civil War-era fort perched right in the middle of the ocean. Make sure to bring your camera because this place is unbelievably scenic!

The water is crystal-clear, the coral reefs are teeming with marine life, and you might spot sea turtles, colorful fish, and even the occasional nurse shark if you decide to snorkel. It’s a full-day trip, but it’s worth every minute for its natural beauty and fascinating history.

If You Prefer Staying Closer to Key West

Book a Jet Ski tour around the island. Zoom past hidden mangroves, skim across turquoise waters, and pause at a sandbar for a quick dip. Keep your eyes peeled for playful dolphins and graceful rays along the way. It’s a thrilling new perspective on Key West’s coastline without having to venture too far or break the bank.

Afternoon: Lunch & a Leisurely Bike Ride

After your morning escapades, you’ll likely be ravenous. Head over to Historic Seaport for a waterfront lunch. Alternatively, swing by Kaya Island.

Once refueled, hit the streets for a laid-back bike ride around Old Town. You’ll find plenty of rentals offering comfy cruisers. As you pedal along, you’ll pass quaint conch-style homes and streets brimming with Key West’s charming, carefree vibe.

This is the perfect chance to check out any corners of the island you might’ve missed and pick up those last-minute souvenirs.

Evening: Mallory Square Sunset Celebration or Dinner on Sunset Key

You’ve come this far, so don’t leave without one final, jaw-dropping Florida Keys sunset.

• Mallory Square Sunset Celebration
  A true Key West tradition, this nightly festivity brings together street performers, live music, and local food vendors. Crowds gather to watch the sun sink into the Gulf of Mexico, painting the sky in dreamy shades of orange and pink.
• Dinner on Sunset Key
  Craving something more serene? Take the short 7-minute ferry ride to Sunset Key and treat yourself to a romantic dinner. The views are spectacular, the ambiance is peaceful, and the seafood is top-notch. Toast your final night with the golden sky as your backdrop—it’s an unforgettable way to bid adiós to the Keys.

By the end of Day 5, you’ll be brimming with stories of marine life sightings, quirky island moments, and postcard-worthy sunsets. As you head out, you’ll already be dreaming of your next tropical escape back to the Florida Keys!

Final Thoughts

We hope this five-day Florida Keys itinerary has guided you to the most experienced road trip adventure in the Florida Keys. How much does this remarkable destination have to offer? a road trip along the Keys deserves a spot on everyone’s bucket list.

Often, friends and travelers visit only Key West, but overlooking places like Islamorada does the Keys a disservice. Whether you’re snorkeling around Alligator Reef Lighthouse, exploring the Seven Mile Bridge. or enjoying a spectacular sunset in Key West, you’ll find unforgettable moments at every turn in the Florida Keys!