An Unforgettable 5-Day Road Trip from Miami to Key West

This blog outlines our recommended Miami to Key West road trip – a perfect long weekend getaway.

Our easy-to-follow 4-day Florida Keys itinerary is an excellent starting point, whether you’re planning a short trip or an extended stay in the Keys.

We kick off the trip with a night in Miami, where you can explore vibrant neighbourhoods, indulge in world-class dining, and enjoy exceptional shopping.

If you’re driving down to Key West, we highly recommend making a few stops along the way. Take some time – be it a couple of hours or even a few days – to explore the stunning beaches scattered throughout the Florida Keys. These scenic detours will make your journey even more memorable.

While flying from Miami to Key West is an option, it’s not the most practical. By the time you check in two hours before your flight and endure the 50-minute journey – barely reaching cruising altitude before descending, it’s clear that driving offers a far more rewarding experience.

We suggest renting a car from Miami airport with booked accommodation along the way.

Driving in Miami is a truly unique experience, offering a mix of urban excitement and relaxed coastal vibes as you transition into the serene landscapes of the Florida Keys. For those renting a car, you’ll find plenty of options to suit your style and needs, from reliable sedans like the Toyota Corolla to roomy SUVs ideal for families or groups. If you want to elevate your road trip experience, consider indulging in a soft top convertible – imagine cruising along the Overseas Highway with the sun on your face and the ocean breeze in your hair! While navigating Miami’s bustling streets may seem daunting at first, the roads are well-maintained, signage is clear, and local drivers are generally accustomed to tourists. Plus, with GPS navigation and the assurance of rental companies providing road support, you can hit the road with confidence and focus on the enjoyable adventure ahead.

The journey from Miami to Key West isn’t just a drive – it’s an unforgettable adventure. Spanning about three hours by car, this scenic road trip is the perfect escape. With endless blue skies and breathtaking ocean views, the route through the Florida Keys is a sensory delight. Whether you’re planning a quick day trip or a longer getaway, Key West offers charm, excitement, and plenty to discover.

Stretching 180 kilometres (113 miles), the Florida Keys are a chain of tropical islands connected by the iconic Overseas Highway. This engineering marvel winds its way gracefully over the Atlantic Ocean, linking each unique key with a series of picturesque bridges. Along the way, you’ll pass mangrove-lined shores and encounter stunning vistas that rise and dip from sea level to sky. Amongst the highlights is the legendary Seven Mile Bridge – an awe-inspiring structure and a perfect spot for capturing postcard-worthy photos.

Driving along the Overseas Highway is a bucket-list experience. Make your adventure even more special by taking a few detours. Stroll along pristine beaches, visit quirky roadside attractions, or savour fresh seafood at charming local eateries. The Florida Keys are brimming with hidden gems, ready to make your road trip extraordinary.

While it’s possible to visit Key West in a single day, extending your trip to four or five days – or even a couple of weeks – lets you fully immerse yourself in everything the Keys have to offer. From the laid-back island vibes to the stunning natural beauty, this road trip is your gateway to an unforgettable escape.

No trip to the Florida Keys is complete without spending at least a night or two in lively Miami! Even if you’ve been before, it’s the perfect chance to discover a new side of this dynamic and exciting city.

Start your exploration in Brickell, a hotspot for trendy restaurants and upscale shopping. Head to Bayside Marketplace, bustling with lively bars, eateries, and unique shops, or venture to South Beach, famous for its spirited energy, excellent restaurants, boutique shopping, and unbeatable people-watching.

For sports fans, attending a baseball game is an experience that shouldn’t be missed, offering an exhilarating atmosphere filled with passionate cheering, iconic ballpark snacks, and the thrill of witnessing America’s favourite pastime up close.

First Stop Options:
Start your journey to Marathon, nestled in the picturesque Middle Keys between Key Largo and Key West. Along the way, make a stop at the Miami Everglades Alligator Park, South Florida’s oldest and most iconic alligator farm, located near the entrance to Everglades National Park. Home to over 2,000 alligators, this unique destination promises an unforgettable adventure. Highlights include an exhilarating airboat tour through the Everglades, a captivating alligator show, and an up-close live feeding demonstration. You can even feed the alligators yourself, immersing you in the rare thrill of being face-to-face with these incredible creatures. Be sure to set aside at least half a day to fully experience this exciting attraction.

Another must-visit destination is Grassy Key, home to the renowned Dolphin Research Center. This nonprofit facility is dedicated to the research, education, and care of dolphins and sea lions, many of whom are rescues or were born on-site. Animals participate in activities entirely by choice, and visitors can book unforgettable experiences, including interactive water sessions.

Next Stop: Marathon
Situated at mile marker 48 (just 115 miles south of Miami and on the approach to Key West’s iconic mile marker 0), Marathon is a captivating destination with the serene allure of island life. For lunch, head to the Castaway Restaurant, a local favourite tucked beside a quiet marina. As Marathon’s longest-standing eatery, it exudes old-school charm with its bar-meets-diner vibe. One of its standout offerings is lionfish, prepared as sushi and presented using the fish’s distinctive head and tail. This culinary choice isn’t just delicious – it’s also an eco-friendly effort to combat the spread of this invasive species threatening the coral reef’s ecosystem.

While in Marathon, don’t miss the Turtle Hospital, a fully operational veterinary hospital dedicated to rescuing, rehabilitating, and releasing sea turtles. Visitors can enjoy an educational guided tour, explore behind the scenes, and even feed some of the turtles up close – a truly enriching experience for animal lovers.

Drive 25 minutes south to reach your hotel for the night…

On your way to Key West, take time to explore the Lower Keys, located between Marathon and Key West. This stretch is home to some fantastic beaches, perfect for a quick stop to soak up the scenery.

Once you arrive in Key West, get ready to fall in love with this charming destination! As the official Mile Marker Zero of Route 1 and the southernmost point of the Florida Keys, it’s a must to snap a selfie by the iconic sign.

Key West is one of Florida’s top spots for a weekend escape. The historic old town, centred around Mallory Square, radiates charm with its cute, colourful streets. Stroll along lively Duval Street, lined with brightly painted wooden shops, inviting restaurants, and bars serving refreshing cocktails, famous key lime pie, and fresh seafood. Don’t forget to browse the boutique shops offering sundresses, souvenirs, and you can even wander into one of the handful of art galleries.

For the best experience, we recommend staying in the quaint old town, where the atmosphere is both relaxing and vibrant. While our itinerary suggests spending one night here, you could easily extend your stay to two or three nights to fully soak in everything this gem has to offer.

We suggest breaking up your return journey with a stay in Islamorada, located just 90 minutes from the airport. This allows for a more relaxed trip and ensures you’re on the safe side in case of traffic, as Highway 1 is a two-lane road that can become congested. The highway tends to get particularly busy on weekends, so staying in Islamorada helps reduce any last-minute stress before your flight.

Things to Do in Islamorada

Explore Robbie’s Marina, a must-visit gem just south of Islamorada at the end of the bridge. This iconic destination offers something for everyone, making it a perfect addition to any Key West road trip. Whether you’re seeking water sports, a casual lunch spot, or a memorable dinner, Robbie’s delivers an experience you won’t forget.

Dive into a variety of activities, from boating and snorkelling to feeding the famous tarpon or browsing for one-of-a-kind souvenirs. Savour a delicious meal by the water with a cold beer in hand, or embark on an adventure by renting a boat and equipment to explore the beautiful surroundings. Whether you spend a few hours or an entire day, Robbie’s vibrant energy and endless options make it worth your time. If you’re just passing through Islamorada, at least stop by for a quick bite – it’s an experience you won’t regret.

For an unforgettable evening, head to Morada Bay and grab a seat on the veranda. Set on a sandy shore that leads directly to the water, this serene spot is perfect for families and friends alike. As the sun dips below the horizon, painting the sky in breathtaking hues, indulge in fresh tortillas and guacamole. It’s the perfect way to end your day in Islamorada, surrounded by good company and stunning views.

As your road trip comes to an end, enjoy a relaxing morning in Islamorada. Take your time soaking up the final moments of your adventure before embarking on the drive back to Miami airport. Once there, you can return your car and prepare to head to your next destination or make your way home.

Key West boasts temperatures ranging from 24 degrees Celsius to the early 30’s all year round, but timing your trip wisely can help you avoid intense heat and heavy crowds.

Winter, from January to March, is the prime season to visit. This is when “snowbirds” flock south to escape the cold, and for good reason. With temperatures in the comfortable mid-to-high 20s and just three to four rainy days per month, it’s an idyllic time to experience Key West’s charm.

On the other hand, June through August brings sweltering heat and high humidity, making it the hottest time of the year. If you’re planning a summer visit, be sure to book accommodation with reliable air conditioning and a pool to cool off during those steamy afternoons!

Keep in mind that September and October mark the peak of hurricane season, offering the lowest prices and smallest crowds of the year.

Whenever you choose to visit, Key West promises a unique and memorable getaway!