Extended Layover in Key West

4 min read

When planning our trip to Key West, we decided to skip the direct flight and instead take the scenic route, flying into Miami and driving down to the southernmost point of the U.S. It’s one of those drives you have to experience at least once—the views are stunning as you cruise across endless stretches of water, hopping from key to key. We added a little nostalgia by making a few stops along the way, especially since I’d spent time in Key Largo years ago.

Miami to Key West

After landing in Miami, we picked up our rental car and hit the road. First stop: Robbie’s Marina in Marathon Key. It’s a great place to stretch your legs, grab lunch and enjoy some gorgeous water views. Robbie’s is known for letting visitors feed the massive tarpon that hang out by the docks, which was definitely fun to watch.

After lunch, we drove straight through to Key West. Yes, the drive is long, but we knew that going in, and the views made it worth it. Once we arrived, we checked into Marrero’s Guest Mansion, the cutest boutique hotel. The location was perfect—just a short walk from all the main spots—and they even provided parking vouchers, which saved us from stressing over where to park.

Exploring Key West

Over the next few days, we tired to pack in as much as possible. Here are a few highlights:

Hemingway House: You can’t visit Key West without a trip to the Ernest Hemingway Home and Museum. The house is beautiful, and if you’re a cat lover, you’ll appreciate the dozens of six-toed cats roaming around—descendants of Hemingway’s own pets. It was interesting to see where one of America’s most famous writers spent his time.

Harry S. Truman’s Winter White House: Another must-see, this home offers a glimpse into the life of a former president who loved escaping to Key West. The history here is fascinating, and the tour gives you a real sense of how important this spot was during Truman’s presidency.

Duval Street: The heart of Key West’s nightlife and shopping scene. We spent time walking along Duval, popping into local shops, grabbing souvenirs and enjoying the lively atmosphere. It’s easy to spend a whole day just wandering and people-watching.

Southernmost Point: We couldn’t leave without getting a picture at the Southernmost Point buoy. Yes, it’s touristy, but it’s also an iconic Key West experience.

Ferry to Sunset Key: One of our favorite parts of the trip was taking a ferry to Sunset Key, a quiet little island just off the coast of Key West. We had afternoon cocktails there at Latitude, a restaurant that offers great food and even better views. It’s a bit of a splurge, but absolutely worth it.

Key West Eats

Key West has an incredible food scene, and we definitely didn’t leave hungry. Some standout spots were:

Kermit’s Key Lime Shoppe: This place is famous for its key lime pie, and for good reason. We grabbed a slice and relaxed in the little courtyard behind the shop—definitely one of the best desserts of the trip.

Moondog Cafe: A great spot for breakfast or lunch, with a relaxed atmosphere and solid food. Perfect for a quick stop before diving into the day’s activities.

Blackfin Bistro: Located on Duval Street, this place was a great find for dinner. The food was fresh, and the bistro has a cozy, upscale vibe that made for a nice change from the usual casual Key West fare.

22&Co: A colorful, quirky bar that’s full of energy. It’s a great place to grab drinks and take in the unique character of Key West nightlife. I might even own a nice tshirt from them now. ;)

Sloppy Joe’s: A Key West classic. It’s loud, lively and full of history. We stopped by for drinks, and it was a great way to soak in the local culture.

Back to Miami

After a few scorching hot [HUMID] days exploring Key West, it was time to head back to Miami. On a last-minute whim, we decided to spend our final night there, so we grabbed a room at Local House Miami, a boutique hotel right near South Beach. It was the perfect spot—chic, cozy and just steps from the beach. We spent the day relaxing by the water, soaking in the last bit of sun before capping off the trip with a legendary meal at Joe’s Stone Crab. Seriously, this place is a Miami institution, and the stone crab claws? Absolute perfection. It’s the kind of meal that lives up to every bit of its reputation.

This trip to Key West was a perfect mix of history, great food and tropical vibes. Driving down from Miami was an experience in itself, and while we’d definitely fly next time to save time, we’re glad we did it once. It’s amazing how much you can pack into a short trip with the right planning, and Key West is a perfect destination for a quick, memorable getaway. Extended Layover in Key West.