A National Park, Key Lime Pie & Hemingway: 3-Days in Key West

The drive from Miami to Key West is part of the adventure, and day one is all about embracing those classic Overseas Highway stops that make the Keys feel so nostalgic and fun. Your first stop should be Hog Heaven Sports Bar & Grill, located in Islamorada (around Mile Marker 85). It’s the perfect midway break, casual, waterfront, and great for stretching your legs with a drink or quick bite right on the marina.

A few minutes down the road, spend some time in Islamorada, one of the most charming sections of the Upper Keys. This is where you’ll find Robbie’s Marina, home of the famous “feed the tarpon” experience. Buy a bucket of bait and get ready for the tarpon to leap right out of the water. It’s a must-do at least once.

For lunch or a fresh-catch snack, I recommend stopping at The Keys Fishery in Marathon. It’s super laid-back, right on the water, and known for unbelievably fresh seafood and their famous lobster Reuben. It’s the ideal place to soak up that “slow Keys” feeling before continuing your drive south.

Day two is all about the bucket-list moment: a full-day adventure to Dry Tortugas National Park, one of the most remote and breathtaking national parks in the US. You’ll depart Key West early in the morning on the Yankee Freedom Ferry, so plan to arrive at the terminal at least 30–45 minutes early to check in, grab coffee at Cuban Queen as you make your way to the marina, and find good seats on the ferry.

The ferry ride itself is part of the magic, about two hours across open water, watching the color shift from deep blue to the bright turquoise that the Dry Tortugas are famous for. Once you arrive, you’ll have several hours to explore Fort Jefferson, swim or snorkel off the white-sand beaches, and enjoy the surreal feeling of being on a tiny island in the middle of the Gulf of Mexico.

Tips for travelers:

• Bring Dramamine if you’re sensitive to motion—the morning ride can be choppy.

• Pack sun protection: a hat, reef-safe sunscreen, sunglasses, and a rash guard if you burn easily.

• Wear your swimsuit under your clothes so you can jump right into the water upon arrival.

• A dry bag is a game-changer for keeping your phone, camera, and towel safe on the beach.

• Lunch is included on the ferry, but bring extra snacks and plenty of water.

• If you want the best photos, head to the moat wall—it’s iconic.

• Don’t skip the ranger-led fort talk—it brings the history of the island to life.

Your final day is dedicated to all the Key West essentials, the iconic spots that give the island its charm, culture, and unmistakable character. Start your morning with brunch at Blue Heaven, one of the most beloved institutions in Key West. The roosters, outdoor garden setting, live music, and mile-high meringue make it a must-experience. If you prefer something quicker, you can always swing by Cuban Coffee Queen for strong Cuban coffee and a breakfast sandwich.

Next, head to the Hemingway Home & Museum, where you can tour the house, wander the tropical gardens, and meet the famous six-toed cats. It’s a perfect blend of literary history and Key West quirk. From there, walk over to Truman’s Little White House or Fort Zachary Taylor State Park if you want a mix of history and beautiful ocean views.

No Key West day is complete without indulging in key lime pie. Stop by Kermit’s Key Lime Shoppe (your personal favorite), and if you want to compare, grab a slice from Blue Heaven or Key Lime Pie Bakery to decide which version wins the day.