Ultimate Road Trip Itinerary from Miami to Key West with Must-See Sights and Top Recommendations

The journey from Miami to Key west could be done in a 45 minute flight, but if you have the time then this road trip (between 3 to 4 hours total driving time) is highly recommended - it's a fantastic way to see the sights and enjoy the activities of the Florida Keys along the way. If it's your first time in the keys and you can spare the time, ideally allow 2 nights so you can stop off and make the most of it. Its one single highway (US-1 / Overseas Highway) all the way, so its an easy drive and you wont get lost! This journey along the Overseas Highway is packed with unique stops, delicious food, and cozy places to stay. Whether you’re chasing adventure, relaxation, or a bit of both, this itinerary covers the best sights and experiences from Miami through Fort Lauderdale, Key Largo, Islamorada, Marathon and Big Pine Key, ending in the tropical paradise of Key West.

Overseas Highway crossing turquoise waters near Key Largo

Starting point: Miami, Fort Lauderdale or Hollywood Beach

Usually flights land late in the afternoon or in the evening, so you might want to stop off in one of Miami, Fort Lauderdale or Hollywood Beach.

Miami

Miami’s vibrant street art and beaches are worth a quick visit if time allows. Its nice to do a walk along the iconic South Beach, and enjoy the art-deco architecture along the seafront, where you'll also find family-friendly restaurants, chains etc.

Fort Lauderdale

About 30 miles North is Fort Lauderdale (OK its a slight diversion but maybe worth it depending on what you're looking for - we like the downtown here for breweries and shopping, and the live music in dive bars along the beachfront). Known as the “Venice of America,” Fort Lauderdale offers beautiful canals and a lively waterfront. Stop at Las Olas Boulevard for boutique shopping, art galleries, and a wine tasting at Sixty Vines with nice accompanying sourdough pizza!

For a drink, I like El Camino, a lively bar with a really good Happy Hour - I've had proper nice craft beers here for just 3 bucks. There's a ton of bars in the downtown area, including a Dueling Piano bar (Howl at the Moon). There's also a brewery quarter of the town - we like to start at the Sistrunk where they have street food trucks, and then have a walk around the other local breweries. Then head to Fort Lauderdale Beach to visit the dive bars with live music, such as the legendary Elbo Room - they have live music every night but the highlights are the lively full bands they squeeze into a corner stage at weekends

Fort Lauderdale also has a nice beach, 7 miles of shoreline with a beachside promenade.

Hollywood Beach

Fort Lauderdale to Key Largo: Gateway to the Keys

From any of Miami, Fort Lauderdale or Hollywood Beach, head south to US-1 for about 60 miles to Key Largo, the first of the Florida Keys. This stretch introduces you to the iconic Overseas Highway, with ocean views on both sides.

Key Largo is famous for its underwater adventures. Visit John Pennekamp Coral Reef State Park, the first underwater park in the U.S., where you can snorkel or take a glass-bottom boat tour to see vibrant coral reefs and marine life.

For lunch, try Mrs. Mac’s Kitchen, a local favorite serving fresh seafood and Key Lime pie. In the evening, enjoy a cocktail at The Fish House Encore, known for its laid-back vibe and fresh catches.

Stay at the Playa Largo Resort & Spa, which offers beautiful waterfront rooms and a relaxing atmosphere perfect for unwinding after a day of exploring.

Key Largo to Islamorada: Art, History, and Island Charm

The drive from Key Largo to Islamorada is about 20 miles, but it’s packed with things to see. Islamorada is known as the “Village of Islands” and offers a mix of art, history, and outdoor activities.

Stop at the Theater of the Sea, a marine mammal park where you can swim with dolphins or sea lions. For a cultural stop, visit the History of Diving Museum to learn about the Keys’ underwater heritage.

Lunch at Morada Bay Beach Café is a must. This beachfront spot serves fresh seafood with stunning sunset views. For a casual drink, check out Green Turtle Inn, a historic bar with a friendly atmosphere and great cocktails.

Consider staying at Cheeca Lodge & Spa, a resort with lush gardens, a private beach, and excellent amenities.

Islamorada to Big Pine Key: Nature and Wildlife

Next, drive about 30 miles to Big Pine Key, a quieter island known for its natural beauty and wildlife. The National Key Deer Refuge is the highlight here, home to the tiny and endangered Key deer. Drive slowly and keep an eye out for these gentle creatures.

Explore the Blue Hole, a freshwater pond surrounded by tropical foliage, perfect for a short hike and birdwatching.

For a meal, try No Name Pub, a quirky spot famous for its seafood and laid-back vibe. It’s a great place to mingle with locals and enjoy fresh fish sandwiches.

Accommodation options here are limited but cozy. The Big Pine Key Fishing Lodge offers simple, comfortable rooms and easy access to nature.

Sunset over Key West harbor with boats docked

Big Pine Key to Key West: The Final Stretch to Paradise

The last leg to Key West is about 30 miles and brings you to the southernmost point of the continental U.S. Key West is a lively island with a rich history and plenty to explore.

Start with a visit to the Ernest Hemingway Home and Museum to see where the famous writer lived and worked. Walk down Duval Street for shopping, bars, and street performers.

For lunch, Blue Heaven offers Caribbean-inspired dishes in a colorful, open-air setting. Don’t miss their famous Key Lime pie.

In the evening, enjoy a sunset cocktail at Mallory Square, where street performers gather nightly to celebrate the sunset. For dinner, Latitudes on Sunset Key offers upscale dining with ocean views, perfect for a special night out.

Stay at the Southernmost Beach Resort for a blend of comfort and beach access, or try the Heron House for a charming boutique hotel experience.