My Ultimate 2-Week Miami to Key West Road Trip

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The first time I drove from Miami to Key West, I thought I knew what to expect…blue water, palm trees, and a few nice beaches. But the Overseas Highway is so much more than a scenic road. It is a chain of tropical islands strung together by bridges, each one with its own rhythm, flavors, and stories.

This is a trip where you can have Cuban coffee in Little Havana at sunrise, snorkel coral reefs by midday, and watch the sun melt into the Gulf from a pier in Key West that same evening. It is one of my favorite drives in the U.S., and over the years I have learned exactly where to stop to get the most out of the experience. Here’s my guide that up until now, I’ve only shared with family and friends.

• Read also: My Guide to the Prettiest Places in the Florida Keys

Planning the Perfect Miami to Key West Road Trip

I have done this route as a quick weekend escape and as a slow two-week wander, and each version has its magic. Two weeks lets you dive into every island, sample more seafood shacks, and spend full days exploring parks like Biscayne and Everglades. Even a three- or four-day trip, though, is enough for a taste of the Keys’ laid-back life.

The Overseas Highway is only about 113 miles long, but it is not a drive you rush. Between Miami and Key West, there are countless reasons to pull over…pastel-painted towns, hidden beaches, family-run seafood joints, and bridges with panoramic views you will want to photograph from every angle.

Below, I have broken the trip into easy stages so you can move at your own pace. Whether you are looking for world-class diving, history, island hopping, or simply a slow coastal cruise, this itinerary will help you make the most of every mile.

Road Trip Itinerary Map for Miami to Key West

This map outlines the key destinations along the road from Miami to Key West. Each stop will be explored in detail below, offering tips to optimize your travel route for a smooth and enjoyable trip.

Days 1-2: Miami, Florida

I always start my road trip in Miami with a couple of days to get into the rhythm of South Florida. It is a city of contrasts. I love the sleek high-rises shadowing sandy beaches, Latin music spilling out of open-air cafés, and quiet botanical gardens tucked between busy streets.

If you arrive early, head straight to the beach. I like to rent a cruiser bike and ride the paved path along South Beach in the morning when the light is soft and the air is still cool. The ocean sparkles turquoise here, and you can stop for a cortadito at a corner café before the crowds arrive.

In the evenings, I wander through Wynwood, where the murals change so often that even locals are surprised week to week. The smell of fresh tacos mixes with craft beer and spray paint, and there is always a band or DJ setting the vibe.

Must-See Spots in Miami

• Miami Beach and South Beach: Sunbathe on the wide sands, then explore the pastel Art Deco buildings along Ocean Drive. I like grabbing a table outside at one of the small Cuban cafés nearby for a plate of croquetas and a cafecito.
• Art Deco Historic District: Join a guided walking tour to hear the backstories behind the neon-lit hotels and geometric façades. Sunset is my favorite time…the buildings glow against the fading sky.
• Little Havana: Stroll Calle Ocho, watch locals play dominoes at Maximo Gomez Park, and sample guava pastries fresh from the oven. Stop at Ball & Chain for live salsa music if you have the energy at night.
• Wynwood Walls: Wander through bold, colorful murals from world-class street artists. There are plenty of side streets worth exploring too, where small galleries and hidden cafés often have no crowds.
• Vizcaya Museum and Gardens: Step into Miami’s Gilded Age at this Italian-style villa. I like to go early, walk the manicured gardens, and then sit by Biscayne Bay watching boats pass.

Additional Miami Highlights

• Pérez Art Museum Miami (PAMM): Striking modern architecture and a collection that spans global and local art. The terrace has gorgeous bay views.
• Miami Design District: Window-shop your way through high-end fashion stores and art installations. Even if you are not buying, the area is a creative feast.
• Bayfront Park: A peaceful place to watch the sun come up over Biscayne Bay. Pack breakfast to enjoy on the grass.
• Miami Seaquarium: A good family stop for dolphin and sea lion shows, one of the best hidden gems in Miami.
• Jungle Island: Close-up encounters with exotic animals in a lush, tropical setting.

Miami sets the tone for the road trip, as it’s colorful, energetic, and full of flavors from around the world. By the time I head south toward the Keys, I am already in that vacation mindset.

• Read also: My Guide to South Beach’s Top Attractions

Day 3: Key Biscayne, Florida

Whenever I need a breather from Miami’s buzz, I make the short drive over the Rickenbacker Causeway to Key Biscayne. It feels like slipping into another world — the skyline fades in the rearview mirror, the air smells of salt and mangroves, and everything slows down.

Key Biscayne is small enough to explore in a single day, but I like to take my time here. In the morning, I’ll grab a breakfast sandwich from a local café in town, then head straight to the beach before the midday sun. The water is calm and clear, perfect for a swim or just floating while pelicans dive nearby.

Top Attractions in Key Biscayne

• Bill Baggs Cape Florida State Park: My go-to spot for a quiet beach day. The historic Cape Florida Lighthouse is worth the climb for sweeping views of the Atlantic and Biscayne Bay. I usually bring a picnic to enjoy under the sea grape trees.
• Crandon Park: Two miles of beach, shallow turquoise water, and a laid-back vibe. Families love it for the calm surf, but I come for the nature center and the chance to spot herons and iguanas on the trails.
• Miami Seaquarium: Technically on nearby Virginia Key, it is an easy stop if you are traveling with kids or are fascinated by marine life. Dolphin and sea lion shows happen throughout the day.
• Cape Florida Lighthouse: Beyond the views, the lighthouse has a fascinating history dating back to 1825. The volunteer guides tell stories about shipwrecks, pirates, and the lighthouse keeper’s life.

I find Key Biscayne especially lovely in the winter and spring, when the humidity is low and the water feels refreshing rather than bath-warm. By evening, I usually drive back to the mainland with the windows down, watching the city lights reappear across the bay.

Days 4-6: Homestead, Everglades & Biscayne National Park

This is where the Miami-to-Key-West drive starts to feel like an adventure. As soon as I pass the last stretch of suburban sprawl, the landscape shifts — fields of tropical fruit trees, roadside stands stacked with coconuts, and air so thick with humidity it feels like you’re already in the Everglades.

I like basing myself in Homestead for a few nights because it puts me within easy reach of two incredible but totally different national parks: the sawgrass wilderness of the Everglades and the turquoise waters of Biscayne. It also means I can end my days with a plate of fresh seafood or a Cuban sandwich without paying Miami prices.

Everglades National Park

I love the the Everglades, as it’s totally different from other national parks in the US. I usually start my mornings here early, before the sun turns the wetlands into an oven. Ernest F. Coe Visitor Center. The Anhinga Trail is a short boardwalk loop that almost guarantees close encounters with wildlife — I’ve seen everything from purple gallinules to gators floating just below the surface.

For something quieter, I’ll wander the Gumbo Limbo Trail, shaded by tropical hardwoods, or climb the Shark Valley Observation Tower for a panoramic sweep of the river of grass. If you want a thrill, nothing beats skimming across the marsh on an airboat, wind in your face, with egrets taking off in your wake.

Biscayne National Park

Where the Everglades is all about what’s on land, Biscayne is almost entirely water. I stop at the Dante Fascell Visitor Center first to check the weather and sign up for tours. Snorkeling the Maritime Heritage Trail is like swimming through a history book — shipwrecks overgrown with coral, schools of parrotfish glinting in the light.

If I’m not in the mood to get wet, I’ll rent a kayak and paddle through the mangrove tunnels, listening to the slap of mullet in the shallows and the rustle of leaves in the breeze. Elliott Key is my favorite for a picnic, while Boca Chita Key has that iconic lighthouse and some of the best views in the park.

Other Unique Stops in Homestead

• Fruit and Spice Park: A living catalog of more than 500 edible plants from around the globe. I’ve sampled fruits here that I’d never even heard of before.
• Coral Castle: Built single-handedly from coral rock, it’s part folk art, part mystery. The story of how it was made is as fascinating as the carvings themselves.
• Robert Is Here Fruit Stand: This is not just a fruit stand — it’s a local institution. Their key lime milkshakes are the stuff of legend.
• Everglades Alligator Farm: A chance to see gators up close and learn about their role in the ecosystem. Airboat rides leave right from the property.

Homestead is best in the winter and spring, when the mosquitoes are less relentless and the days are warm but not stifling. After a few days here, I always feel ready to swap the wetlands for open water and start the drive into the Keys.

Days 7-8: Key Largo, Florida

Continue your adventure down the Overseas Highway and you’ll encounter Key Largo, known as the “Diving Capital of the World”. It’s the perfect spot for underwater adventures and relaxing by the sea. With its stunning coral reefs, marine sanctuaries, and a variety of water activities, Key Largo offers something for every traveler.

Top Things to Do in Key Largo

• John Pennekamp Coral Reef State Park: Snorkel, dive, or take a glass-bottom boat to see colorful reefs and marine life. The Christ of the Abyss statue underwater is a haunting and beautiful sight.
• Florida Keys National Marine Sanctuary: A protected marine wonderland with coral reefs, tropical fish, and historic shipwrecks. Dive shops in town can arrange trips to the best spots.
• Dagny Johnson Key Largo Hammock Botanical State Park: I like to spend an early morning walking these shady trails, looking for rare birds and butterflies.
• African Queen Canal Cruise: Step aboard the actual steamboat from the 1951 film The African Queen for a narrated ride through Key Largo’s waterways.
• Jules’ Undersea Lodge: If you’re feeling adventurous, you can actually stay overnight in this submerged hotel. You scuba dive in to check in.
• Key Largo Fisheries Backyard Café: Order the fresh catch of the day and eat it on the dock while pelicans hover nearby, hoping for scraps.

Key Largo has plenty of waterfront inns and resorts, but I tend to pick smaller places with a dock where I can watch the sunset without leaving “home.” Two days here is enough to explore, but it’s easy to lose track of time when the water is this clear.

Days 9-10: Islamorada, Florida

By the time I reach Islamorada, I’ve settled into island time. This “Village of Islands” has a way of slowing me down even more — the fishing boats drifting back to dock in the late afternoon, the smell of grilled mahi in the air, and sunsets that seem to last forever.

I like to start my mornings here on the water. Islamorada is legendary for sport fishing, so booking a half-day charter means fresh snapper or grouper for dinner. But even if fishing isn’t your thing, there are plenty of ways to enjoy this stretch of the Keys.

My Favorite Stops in Islamorada

• Theater of the Sea: A mix of marine park and family-run charm. I’ve swum with dolphins here, and the staff’s passion for animal care really shows.
• History of Diving Museum: Fascinating exhibits on everything from early diving helmets to deep-sea exploration. It’s small enough to enjoy in under an hour but packed with stories.
• Anne’s Beach: A local favorite for shallow, warm water and picnics. The boardwalk here winds through mangroves with little sandy coves to claim as your own.
• Windley Key Fossil Reef Geological State Park: A walk through an ancient coral reef turned quarry. The fossilized coral formations are incredible up close.
• Morada Bay Beach Café: Dinner here with toes in the sand and live music in the background is one of my Islamorada traditions.

Islamorada is compact, so I often rent a bike to move between beaches, cafés, and galleries without worrying about parking. By the end of two days here, I’m usually sun-soaked, salt-haired, and perfectly content to keep drifting south toward Marathon.

Day 11: Marathon, Florida

Marathon is where the Overseas Highway really stretches its legs with long ribbons of road skimming just above turquoise water. I like to slow down here and soak up the “middle Keys” vibe before crossing the Seven Mile Bridge into the Lower Keys.

This small city is spread over 13 islands, so life here revolves around the water. One of my favorite ways to start the day is at Sombrero Beach. It’s calm, family-friendly, and the kind of place where you’ll see both kids building sandcastles and locals launching kayaks.

Marathon Highlights

• Dolphin Research Center: An educational facility where you can meet dolphins and sea lions up close. I’ve joined one of their interactive programs before, and it was an unforgettable experience — not just for the fun, but for learning about marine conservation.
• Sombrero Beach: A soft-sand stretch perfect for swimming, sunbathing, and picnics. I recommend packing lunch and spending at least a few hours here.
• Seven Mile Bridge: Driving across is spectacular, but I like to stop at the pedestrian-accessible Old Seven Mile Bridge for the views and the breeze.
• Crane Point Hammock: A lush nature preserve with trails through tropical hardwoods, a small history museum, and the historic Adderley House.
• Turtle Hospital: A must-do for animal lovers. The guided tours take you behind the scenes to see how injured sea turtles are treated and released.

For food, I usually end up at a dockside spot like Keys Fisheries for lobster Reubens or fish tacos. By the time the sun sets over the Gulf, I’m ready to get an early night so I can make the most of the drive to Big Pine Key the next morning.

• Read next: My Favorite Airbnbs in the Florida Keys

Day 12: Big Pine Key, Florida

Whenever I reach Big Pine Key, the pace of life drops another notch. This is the start of the Lower Keys — quieter, less developed, and full of hidden natural beauty. It’s also home to one of the most unique residents in the state: the endangered Key deer. I’ve spotted them grazing along the roadside at sunrise, their delicate frames and curious eyes making them look like miniature whitetails.

I like to begin my day at Bahia Honda State Park. Its beaches are some of the prettiest in Florida, with powdery sand and water so clear you can see the shadow of a pelican flying overhead. Snorkeling here feels like swimming in an aquarium, and the views from the old Bahia Honda Rail Bridge are unbeatable.

Big Pine Key Highlights

• Bahia Honda State Park: Swim, snorkel, or kayak in calm, turquoise water. I always pack a picnic and make a day of it.
• National Key Deer Refuge: Drive slowly and keep your camera ready. The refuge’s trails are peaceful, and if you’re patient, you’re almost guaranteed a deer sighting.
• Looe Key Reef Resort and Dive Center: Great for a half-day snorkel or dive trip to one of the healthiest coral reefs in the Keys.
• No Name Key: A tiny, quiet island perfect for kayaking or simply enjoying the solitude. It’s also one of the best stargazing spots I’ve found in the Keys.
• Big Pine Flea Market: If you’re here on a weekend, stop by for local produce, crafts, and quirky souvenirs.

Big Pine Key is one of those places that invites you to slow down…linger on the beach, paddle through the mangroves, watch the sky turn from gold to pink to deep indigo. By the time I leave, I’m completely reset and ready for the final stretch into Key West.

Days 13-16: Key West, Florida

Rolling into Key West always feels like reaching the end of the world. The Overseas Highway literally stops here, with nothing but open water between you and Cuba. The colors seem richer, the air warmer, and the streets buzz with a mix of history, eccentricity, and pure island charm. I like to give myself at least three days here so I can balance sightseeing with lazy afternoons by the water.

Day 13: First Taste of Key West

I usually kick things off at the Ernest Hemingway Home and Museum. The house itself is gorgeous, but it’s the six-toed cats lounging in the shade that steal the show. From there, I wander down to Mallory Square in the late afternoon for the famous Sunset Celebration with street performers, live music, and the kind of sunsets that make you stop mid-sentence. After dark, I follow the hum of music to Duval Street, where I might end up at Sloppy Joe’s Bar for a rum cocktail and some live tunes.

Day 14: History and Coastal Views

I like to start with the classic Southernmost Point Buoy photo op before the crowds arrive. Then it’s off to Fort Zachary Taylor Historic State Park, where I can explore Civil War–era history and then slip into the water for snorkeling right off the beach. In the afternoon, I wander through the Key West Butterfly and Nature Conservatory, where hundreds of butterflies float through warm, fragrant air. Dinner is often fresh grouper at a waterfront spot, with my toes in the sand.

Day 15: Dry Tortugas National Park

This is an early wake-up day. Whether you take the ferry or a seaplane, the trip out to Dry Tortugas is worth every minute. Fort Jefferson is massive and fascinating, but the real magic is in the water…snorkeling around the fort walls where parrotfish dart among coral and sea turtles glide by. I usually spend the ride back napping in the sun, still smelling of saltwater.

Day 16: Final Day in Key West

On my last morning, I make time for the Truman Little White House, where you can walk through the winter retreat of President Harry S. Truman. Then I climb the Key West Lighthouse for one last panoramic view of the island. My final stop is often lunch at Latitudes on Sunset Key…a short ferry ride away, with food and views that make it hard to leave.

For me, the magic of Key West is in its mix: deep history, quirky characters, and water that seems to glow at sunset. I leave every time thinking about when I’ll be back.

Other Destinations to Consider When Road Tripping from Miami to Key West

If you’ve got extra days to play with, there are some great detours and side trips that can make your Miami-to-Key-West drive even richer. I’ve taken a few of these either before starting the Overseas Highway or on the way back north, and each one adds its own flavor to a South Florida itinerary.

• Everglades City & Big Cypress National Preserve: If you loved the Everglades but want to see a wilder, quieter side, head for Everglades City. The airboat rides here feel more intimate, skimming through mangrove tunnels with the occasional osprey overhead. Big Cypress is right next door — a mix of cypress swamps, boardwalk trails, and some of the best wildlife viewing I’ve had in Florida.
• Naples, Florida: Naples has a polished, resort-town feel with sugar-white beaches and a historic pier that’s perfect for sunset strolls. I like wandering Fifth Avenue South for its cafes and galleries, then ending the day watching dolphins cruise past the pier.
• Marco Island: The pace slows even further on Marco Island. Tigertail Beach is great for shelling, and if you want complete solitude, you can boat out to Keewaydin Island — no roads, no shops, just sand and sea.
• Fort Myers & Sanibel Island: From Fort Myers, it’s an easy hop to Sanibel Island, famous for beaches covered in seashells and the wildlife-rich J.N. “Ding” Darling National Wildlife Refuge. Back in Fort Myers, touring the Edison and Ford Winter Estates feels like stepping into a time capsule from Florida’s early resort days.

If you’re not ready to head straight home from Key West, you can also double back to explore the Lower Keys a bit more. Kayaking the backcountry waters around Big Pine or snorkeling at Bahia Honda for one more look at the reef is the perfect way to extend the trip.

Things to Consider When Planning Your Southern Florida Road Trip

If you’re not ready to head straight home from Key West, you can also double back to explore the Lower Keys a bit more. Kayaking the backcountry waters around Big Pine or snorkeling at Bahia Honda for one more look at the reef is the perfect way to extend the trip.

• Read also: My Favorite Spots to Visit in South Florida

Where to Start Your Trip

I usually begin in Miami. It’s got direct flights from all over, plenty of rental car options, and a mix of beaches, nightlife, and culture that gets you in the right vacation mindset. Before hitting the road, I like to wander the Art Deco District, sip a cafecito in Little Havana, and take a sunset walk on South Beach.

Some travelers choose to fly into Key West and work their way north, but I prefer starting in Miami so I can watch the scenery get more tropical with every mile.

Picking the Right Car

The drive is smooth and paved, so you don’t need anything rugged, but you do want something comfortable with good gas mileage. I’ve done it in a convertible once, and I’ll admit, top-down cruising past turquoise water is hard to beat. PS: If you want to rent a car, I highly recommend Discover Cars to find the best rates!

Best Time to Go

• Winter (Dec–Feb): Perfect weather and blue skies. It’s the busiest season, so book early and expect higher prices.
• Spring (Mar–May): Warm days without the winter crowds. My favorite time for snorkeling and kayaking.
• Summer (Jun–Aug): Hot, humid, and often stormy in the afternoons, but you’ll find better deals and quieter beaches.
• Fall (Sep–Nov): Hurricane season. If you go, keep an eye on forecasts. By late fall, the weather cools and crowds are still light.

How Long You’ll Need

If all you want is the drive, you can technically go Miami to Key West in a single day — but you’ll miss the magic. I think 4–5 days is the sweet spot for hitting the highlights. If you can stretch it to a week or more, you can add side trips, linger at your favorite beaches, and really get to know the islands.

FAQs About Miami to Key West Itinerary

Here are some popular questions I get asked about road trips from Miami to the Keys:

How long should I spend driving from Miami to Key West?

I like to give myself at least two full days for the drive down so I can actually enjoy the stops instead of just blasting through. You could technically do it in about four hours without stopping, but that would mean skipping all the beaches, parks, and quirky little towns that make this route so special.

Do I need to book accommodations in advance?

If you are traveling between December and April, absolutely. Winter is peak season in the Keys and places can sell out months ahead. In the summer or fall, you might find last-minute deals, but I still like to lock in at least my Key West stay early.

What should I pack for a Miami to Key West road trip?

Light, breathable clothing, a good pair of sandals, reef-safe sunscreen, sunglasses, and a hat are essentials. I also bring a dry bag for my phone and camera if I am going to be on the water, plus insect repellent for evenings and nature trails.

Is a convertible worth it for this drive?

If you enjoy the sun and breeze, yes. I have done it both ways and the convertible definitely made the drive feel more like an event. Just be ready with sunscreen and a hat, because the Florida sun is strong.

Can I do this trip without a car?

Technically, yes. There are buses and shuttles between Miami and Key West, but they will not stop for sightseeing. The beauty of having your own car is being able to pull over whenever something catches your eye.

What are the must-try foods along the way?

Fresh seafood is everywhere, and I always make time for a plate of conch fritters in Key Largo, a mahi sandwich in Islamorada, and a slice of Key lime pie in Key West. If you see a roadside fruit stand, stop — I once had the best mango of my life at a stand in Homestead.