If you’re planning a Florida Keys itinerary, the drive from Miami to Key West is easily one of the most beautiful road trips in Florida. In the video, I take you along the route, sharing some popular stops along the way—and I also talk about what it’s like to arrive in Key West by cruise. Here you’ll find ideas, tips, and places you can easily add to your plan whether you’re driving through the Keys or visiting Key West for the day on a cruise.
Leaving early makes a big difference. Even though the drive can take about 4 hours without stopping, the truth is… you’ll want to stop a lot. If your plan is to drive all the way to Key West, this is one of those trips to enjoy slowly. The journey itself is part of the experience.
And honestly, even after doing this drive so many times, I still have a little bucket list moment pending: renting a convertible and driving all the way to Key West. Yes, I know… super touristy lol but I feel like it’s one of those things you just have to do at least once! Ready to follow a fun Florida Keys Itinerary? Let’s go! 🙂
If you’re arriving in Key West on a cruise, at least in my case, the ship arrived before sunrise—and I made it a point to wake up early to watch the island come to life. Like I always say, even if you’ve visited a place many times, there’s always something new to experience. That time, it was seeing Key West wake up from the sea… and I loved it.
If you’re driving instead, don’t miss sunset by the harbor or around the Mallory Square area. It’s always a show.
Key Largo: more than just a quick stop
In the video, I stop at Rowell’s Waterfront Park to take a break. But if you have more time, it’s worth exploring John Pennekamp Coral Reef State Park. It’s perfect for snorkeling, kayaking, or just enjoying a natural setting that feels very different from the rest of Florida.
Nearby, you can also visit the Florida Keys Wild Bird Center. It’s a peaceful place where you can walk around and see rescued birds. A short but unique stop.
Tavernier & Islamorada: sweets, views, and experiences
In the video, I mention stops like Rain Barrel Village and Robbie’s of Islamorada—both classics in the area. One of my favorite extra stops (especially if you love desserts) is Key Lime Pie Factory.
In Islamorada, you can also add:
- Theater of the Sea for a more interactive experience
- History of Diving Museum if you want something different and educational
Between stops, take your time to enjoy the views. There are so many spots where simply pulling over is worth it.
Another common stop is by Bass Pro Shops – World Wide Sportsman, which also has a restaurant with a great atmosphere.
A scenic stretch: heading toward Marathon
A couple of times, I’ve stayed in Marathon since it’s usually more affordable than Key West and still about an hour away. It’s also a great way to split the trip into two days.
While in Marathon, you can visit Sombrero Beach and stop by the iconic Seven Mile Bridge (main pic). There’s a small parking area nearby, so you can pull over, enjoy the view, and of course… take some photos.
Close by, don’t miss Bahia Honda State Park, often considered one of the most beautiful beaches in the Keys. Perfect for a longer stop, a swim, or even a picnic.
Beaches along the way (worth the stop!)
If you want to mix in a little beach time during your drive, here are a few great options:
- Anne’s Beach: shallow waters, calm, and great for a quick stop
- Sombrero Beach: one of the most popular and spacious beaches in the Keys
- Bahia Honda State Park: stunning views and clear water
We made it to Key West!
In the video, I walk you through Duval Street, with its lively atmosphere, bars, and shops—plus the experience of arriving by cruise. And of course, I had to stop for a Cuban coffee.
Key West is fun, friendly, and easy to explore. You’ll find small beaches, museums, and even art galleries to enjoy.
If you have more time, consider visiting:
- Ernest Hemingway Home and Museum
- Harry S. Truman Little White House
- Mallory Square at sunset (a must!)
And something you can’t skip: trying Key Lime Pie. Two of my favorite spots are Kermit’s Key Lime Shop and Mattheessen’s Homemade Ice Cream. Both are delicious and perfect to cool off. I still need to do a full “taste test tour” to find my absolute favorite.
Best time to visit
The best time to visit is usually between November and April, when the weather is cooler and drier. Summer is hotter and more humid, but you might find fewer crowds at times. Keep in mind that hurricane season runs from June through November, so rain is more common during those months.
A trip you’ll always want to repeat
This Florida Keys itinerary is one of those trips you can do over and over again, and it always feels different. Whether you drive it or arrive by cruise like I did last time, the Keys have a special energy that keeps calling you back.
If you want to see the full journey, the stops, and the vibe of Key West in action, don’t miss the video below. And if you’ve done this trip before, tell me—what was your favorite stop? What would you add to the list?
