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

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

Click here or Click 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 it takes around 1  2h15m (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 that’s still used today. Each address in the Keys corresponds to its distance from Mile Marker 0 in Key West, which makes it remarkably easy to gauge distances. The markers start at around MM 127.5 in Florida City (mainland) and count down to 0 in 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 while benefiting 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.

Best 5-Day Florida Keys Itinerary

This trip starts and ends at Miami International Airport (MIA), the best airport to fly into for the Keys’ top attractions. Although Miami is where you’ll arrive, the real adventure begins in Key Largo, an hour south, so this is essentially a Key Largo to Key West trip.

Hop in and let this guide take you down sun-kissed highways where blue water stretches out on both sides and the subtropical breeze carries the scent of salt and adventure. Your Florida Keys trip is all about relaxation and discovery.

As you drive south on the Overseas Highway to Key West, each mile brings new surprises – hidden coves, historic landmarks, and the famous Seven Mile Bridge. This stretch of road is some of the best coastal driving in America.

You’ll pass through island towns like Islamorada before reaching iconic Key West. Each stop has its own character and adventure, whether you’re snorkeling in crystal-clear water or jet skiing across the open ocean.

The local wildlife is an added bonus to your trip; you might see manatees swimming in quiet lagoons, dolphins playing in the waves, or sea turtles cruising their ancient marine highways.

The food scene is just as impressive, with everything from fresh seafood prepared with local flair to the region’s signature dessert, tangy and sweet key lime pie.

Whether you’re looking for adventure or just want to sit and watch the sunset, the Florida Keys has it all. Pack your sunscreen; a sense of adventure and tropical fun awaits on these islands.

Things to Know Before Visiting the Florida Keys

Plan Your Dream Keys Adventure: Miami to Key West

Before you start the road trip for your island-hopping adventure through the Florida Keys, here’s your ultimate guide to making the most of this tropical heaven. The Florida Keys offer an incredible array of experiences, from natural wonders to cultural hotspots, ensuring your road trip is filled with unforgettable moments.

Must-See Stops Along the Way:

Renting a Car For Your Florida Keys Drive

You must plan ahead when renting a car from Miami International Airport (MIA). 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 does include rental coverage, ask if you need documentation from your card issuer to confirm this coverage so you don’t get redundant coverage sold 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.

Day 1: Miami to Key Largo

Your First Day in the Florida Keys

Before you dive into the Keys’ crystal waters, take a minute to soak up Miami’s vibe. Whether you’re into Wynwood’s street art or South Beach’s Art Deco heaven, let the city prepare you for the paradise that awaits down the Overseas Highway.

Your Oasis: Kona Kai Resort

In Key Largo, the Kona Kai Resort Gallery and Botanic Gardens is not just a place to crash – it’s where your Keys adventure starts. After the ritual of airports and flying, this is where you’ll land softly for your first two nights in paradise.

A Natural Oasis

Imagine beachfront cottages scattered throughout one of only two frost-free tropical botanical gardens in the continental United States. Tiny lizards and iguanas scurry along the paths, leading you to waterfront views that frame the nightly Keys sunset.

Your Private Getaway

Each cottage has:

• Fully equipped kitchens for cooking
• Private spaces that blend into the surroundings
• Front-row seats on the waterfront

Freebies

We make sure adventure is always at your doorstep:

• Kayaks to explore secret coves
• Stand-up paddleboards for morning strolls
• Paddle boats for afternoon cruises
• A pool and hot tub for total relaxation

The End of Day One

Find your happy place:

• Stretch out on the private dock
• Swing in a hammock under the palms
• Watch the sky change colors
• Drink your favorite cocktail by the water

As the sun sets on your first day, you’ll see why we recommend starting your Keys adventure here. Let Key Largo’s warm breeze and calm waters get you the right mindset for your tropical getaway.

Dinner at Sundowners

Sundowners is a Key Largo favorite for food and sunsets located on the Florida Bay. Waterfront restaurant with a big bar and fresh local seafood.

Since it’s only 15 minutes from Kona Kai, we decided to have an early dinner here. But we found the magic after dinner when we returned to Kona Kai’s private dock to watch the sunset in peace.

Day 2: Around Key Largo and Islamorada

Continue your Florida Keys adventure through Key Largo and Islamorada on day two and uncover the secrets of the northern Florida Keys. Today’s highlight: John Pennekamp Coral Reef State Park, America’s first underwater preserve and some of the best snorkeling in the Florida Keys.

Snorkeling at John Pennekamp Coral Reef State Park

Guarding the entrance to the Florida Keys, John Pennekamp Coral Reef State Park is home to an underwater treasure unlike any other in the continental USA. This marine sanctuary protects the Florida Keys barrier reef system and allows visitors to see an underwater world alive.

What to Do

The park offers:

• Guided snorkeling to the coral reef
• Mangrove walking trails
• Beaches
• Kayaking
• Scuba diving
• Wildlife viewing

Pro Tip: Bring your camera! The park’s coastal areas are full of wildlife, from sunbathing iguanas to various fish species, and you might even see a crocodile near the visitor center.

Plan Your Snorkel

• Reservations: Required, especially in season
• Multiple Tours: Choose from several times a day
• Popular: Tours fill up fast, book early

Snorkeling Highlights

1. Tropical Fish: Swim with the reef fish
2. Coral Reef: See the marine life
3. Christ of the Deep: See the underwater statue

Christ of the Deep: An Underwater Wonder

This 4,000-pound bronze statue, installed in 1961, is a snorkeler’s must-see. While the statue’s hands are raised above the water’s surface, making it visible to snorkelers, be careful:

Best Time to Go

• Early morning tours are best
• Peak season requires reservations
• Check the weather before you book

Mrs. Mac’s Kitchen: The Florida Keys’ Best Restaurant

Looking for the best restaurants in the Florida Keys? Mrs. Mac’s Kitchen is a local institution that should be at the top of your Key Largo dining list. With two locations along the Overseas Highway, this little gem serves up Florida Keys flavor with a side of history.

The Original Location: A Piece of Florida Keys History

The real deal is the original Mrs. Mac’s Kitchen at 99336 Overseas Highway in Key Largo. Walk in, and you’ll see the most famous feature: walls covered with license plates from around the world donated by happy customers. This tradition has become so popular that customers bring their own plates to add to the collection.

What’s Special About the Original:

• Cozy
• Historic
• License plate collection
• Original recipes and cooking

Evening Paradise at Morada Bay Beach Cafe

Located on Islamorada’s beautiful beach, Morada Bay Beach Cafe is the Florida Keys dining experience you’ve been waiting for. This beachfront restaurant combines Caribbean flair with laid-back luxury so you can unwind after a day of adventure. Imagine sitting at a table on the sand, the palm fronds whispering above you as nature’s soundtrack.

As the day winds down, you’ll see why this isn’t just another waterfront restaurant – it’s a destination. The cafe’s location puts you front and center to some of the Key’s best sunsets, painting the sky with oranges and pinks that reflect off the calm waters of Florida Bay. Whether you sit with your toes in the sand or their air-conditioned indoor seating (with equally great views), every table is a dining experience.

Let the tropical breeze and swaying palms get you in the mood as the sun goes down. Enjoy fresh seafood and creative cocktails. The cafe becomes a magical place where time stands still, and the world drifts away with the tide. Stay for dinner, stay for one more drink, and just be in the zone of Keys time.

Day 3: Drive to Key West with Stops Along the Way

As you head south on your Florida Keys adventure, the Seven Mile Bridge is a marvel of human ingenuity and nature. This behemoth of a bridge stretches across 7 miles of open blue water from Marathon to Little Duck Key, with the original bridge running parallel to the new highway. The old bridge used to carry Flagler’s railroad and later a narrow road; today, a 2.2-mile section is a popular spot for cyclists and pedestrians to enjoy the ocean views.

The Florida Keys Wild Bird Center is a great place to stop and take a break on your journey, where wildlife rehabilitation meets public education. This sanctuary has two distinct facilities: the Mission Wild Bird Hospital, where injured birds get expert care, and the Laura Quinn Wild Bird Sanctuary, where permanently injured birds live out their days. The natural mangrove setting gives visitors an up close and personal look into the lives of these amazing creatures while supporting conservation efforts.

Florida Keys Wild Bird Center

Exploring the Laura Quinn Wild Bird Center. is a world of feathered residents, each with their own story. Among them is Booby, a masked booby bird who became a local celebrity when Florida Keys Brewing Company named a limited edition beer after him, with proceeds going to the center’s mission. Throughout the sanctuary are displays that tell the rehabilitation stories of various species, making it an educational experience for all ages.

The center is donation-only, so consider a $10 per person donation that goes directly to their work. This is a great place to stop for families looking for a real wildlife experience, nature photographers wanting to get some great shots, or anyone interested in conservation. You’ll see different bird species up close and help in the ongoing effort to protect and preserve the Keys’ wildlife.

Lunch and Outdoor Activities at Robbie’s of Islamorada

No Florida Keys road trip is complete without a stop at Robbie’s of Islamorada, a legendary marina that’s become one of the region’s most beloved attractions. This waterfront destination offers far more than just a place to grab lunch, though the fish tacos at the Hungry Tarpon Restaurant are absolutely worth writing home about.

What truly makes Robbie’s special is its famous tarpon feeding tradition, which began decades ago when the owner rescued an injured tarpon they named Scarface. After nursing the fish back to health and releasing it, Scarface didn’t just swim away – legend has it he returned with dozens of friends, starting a tradition that continues to this day.

Day 4: Key West Activities

A perfect day in Key West can be had on foot, with all the top attractions within walking distance of the historic district. From the morning bustle of the Historic Seaport, where fishermen bring in their daily catch, to the rich history of the Hemingway Home and its six-toed cats, every corner of Old Town has a story to tell.

Walk down Duval Street, pose for a photo at the Southernmost Point buoy, and climb the Key West Lighthouse for island views – all without a car. When your feet need a rest, hop on the free Duval Loop shuttle, which runs around the main attractions every 15-20 minutes. As the day winds down, join the party at Mallory Square’s Sunset Celebration, where street performers and local artists create an evening like no other that is pure Key West.

The Hemingway Home and Museum

The Ernest Hemingway Home and Museum is one of Key West’s most captivating attractions, where literary history and feline charm intertwine in fascinating ways. During his decade-long residence here (1931-1940), Ernest Hemingway crafted some of his most celebrated works within these Spanish Colonial walls. Still, not just the Nobel Prize winner’s legacy draws visitors.

The home itself, with its elegant limestone architecture, tropical gardens, and first-in-Key West swimming pool, offers a glimpse into the island’s golden age and the lifestyle of one of America’s most iconic writers.

However, what truly sets this historic site apart is its unique permanent residents, a colony of polydactyl (six-toed) cats who live like royalty on the property. The feline tradition began with Snow White, a single white six-toed cat gifted to Hemingway by a ship’s captain, and continues today with approximately 60 cats, many descendants of that original pet.

Key West Butterfly and Nature Conservatory

Step into a magical world at the Key West Butterfly and Nature Conservatory, where what looks like a quaint Victorian house on the outside is a tropical oasis on the inside. This climate-controlled glass conservatory is home to over 50 species of butterflies that float through the air, surrounded by lush tropical plants and waterfalls.

Beyond the butterflies, meet Rhett and Scarlett, two rescued Caribbean flamingos who are the conservatory’s mascots. The soft chirping of exotic birds like Chinese Button Quail and Zebra Finches enhances the peaceful atmosphere. $15 ($12 for seniors and military) is a small price for one of Key West’s most magical experiences. Just plan your visit before 4:30 PM to get the full effect of this tropical wonderland.

Southernmost Point of the Continental US

No trip to Key West is complete without a visit to the Southernmost Point Buoy, one of the most photographed landmarks on the island. This bright blue concrete monument, painted to look like a buoy, marks what’s known as the southernmost point in the continental US (although geography nerds will note the actual southernmost point is on private property a few blocks away).

Standing at the corner of South and Whitehead Streets, the buoy says “90 Miles to Cuba” and is mobbed with photographers all day long. For the best photo without the crowds, go early in the morning when the sun is rising and cast a beautiful glow on this Key West icon.

Walk down Duval Street

The heart of Key West beats along Duval Street, where historic architecture meets modern island life. Stretching from the Gulf of Mexico to the Atlantic Ocean, this vibrant thoroughfare offers an eclectic mix of art galleries, boutique shops, and legendary bars. As you stroll down its sidewalks, you’ll be immersed in the town’s unique blend of Caribbean charm and American history, with the sweet aroma of key lime pie and the sounds of live music drifting through the tropical air.

Sunset Celebration at Mallory Square

Mallory Square becomes a circus every evening during the famous Sunset Celebration in the heart of Key West’s historic waterfront. Two hours before sunset, this lively plaza comes to life with street performers, local artisans, and food vendors all gathering to watch nature’s show as the sun sets into the Gulf of Mexico. Fire jugglers, sword swallowers, and the infamous Cat Man entertain the crowds while local artists display their wares; it’s the perfect Key West vibe.

It’s become such an institution that it’s now an official daily event; locals and tourists alike come to see what many consider the best free show in the Florida Keys – and if you get there early enough to stake out a good spot along the waterfront, you’ll know exactly why.

Truman Little White House

The Truman Little White House is Key West’s presidential legacy, from humble naval quarters built in 1890 to the historic retreat that hosted 6 US Presidents. Harry Truman became famous during his 175-day stay as Commander in Chief, but Taft, Eisenhower, Kennedy, Carter, and Clinton also stayed there. Today, you can tour this piece of American history and walk through rooms just as they were in Truman’s time, including his poker table, where many informal presidential meetings took place. From Cold War strategy sessions to the Cuban Missile Crisis, these walls have seen it all, making it one of Key West’s most interesting historic sites.

Day 5: Key West to Marathon

Don’t just view the drive back to Miami as the end of your Florida Keys adventure. Make it a highlight by spending your last days in Marathon, a charming island an hour north of Key West. This laid-back community has the perfect mix of relaxation and activity; visit the famous Turtle Hospital (book appointments in advance) or unwind at one of the area’s beautiful resorts.

We recommend leaving Key West around mid-morning so you have time for a final Keys breakfast before heading north. Depending on your Turtle Hospital tour time or personal preference, you can either hit Marathon’s attractions right away or take it easy at your resort – after all, you’re still on Keys time! This stop breaks up your drive back to Miami and adds another destination to your Florida Keys experience.

Breakfast at Blue Heaven

Blue Heaven is at the corner of Petronia and Thomas in Key West’s Bahama Village, a brunch institution serving history and great Floridian-Caribbean food. This open-air restaurant, where Ernest Hemingway used to referee boxing matches and was once a brothel and a cockfighting arena, now lets you enjoy lobster benedict and shrimp grits with your toes in the sand under a canopy of tropical trees.

Roosters strut through the courtyard, and local musicians provide the music while you eat some of the Keys’ best brunch in a pure Key West atmosphere. Just be prepared to wait during peak hours, as this local favorite is popular.

Turtle Hospital 

The Turtle Hospital in Marathon is one of the best Florida Keys road trip itineraries. This one-of-a-kind facility is dedicated to rehabilitating endangered sea turtles and offers 90-minute guided tours that give you a behind-the-scenes look at their life-saving work. During your visit, you’ll learn about different sea turtle species and the rehabilitation process and see turtles in their habitat.

Some turtles return to the ocean, and others become permanent residents due to injuries. You get to see them up close. Advanced reservations are required for the tours, which run hourly from 9 am to 4 pm. The tours are $27 for adults and $13 for kids 4-12. Worth it for the conservation and the Keys experience.

Relax at Isla Bella Beach Resort

Finish your Florida Keys adventure with a stay at the beautiful Isla Bella Beach Resort in Marathon. This 24-acre oceanfront resort has gorgeous waterfront villas with Atlantic views so you can relax and reflect on your Keys journey. Five pools are scattered throughout the property, and beachside cabanas are used to lounge the day away.

The beachfront bar’s drinks may be a bit pricey, but the views are worth it. When hunger strikes, you can enjoy authentic Italian cuisine at the on-site restaurant or hop on one of the resort’s free bicycles and ride to nearby restaurants. It’s the perfect blend of luxury and Keys laid back for your last stop.