Sun, salt air, fishing lines, and island time.

The Florida Keys aren’t about flashy resorts or powdery Caribbean beaches. They’re about laid-back island vibes, world-class fishing, chill waterfront happy hours, fresh-off-the-boat seafood, and (in our opinion) the best damn Key Lime Colada you’ll ever taste.
Our favorite Key? Islamorada — the perfect mix of relaxed and lively.
How to Get There
You’ll definitely want to rent a car. The Overseas Highway drive is half the experience — ocean views on both sides, charming roadside stops, and bridges that feel like you’re floating over turquoise water.
Here’s a quick airport breakdown:
✈️ Fort Lauderdale-Hollywood International Airport (FLL)
- About 1.5–2 hours to Islamorada (≈ 90 miles)
- Often the best balance of flight prices and convenience
- Easy rental car pickup
✈️ Miami International Airport (MIA)
- About 1.5 hours to Islamorada (≈ 80 miles)
- Great flight availability
- Slightly busier airport experience
✈️ Key West International Airport (EYW)
- About 1.5 hours south of Islamorada (≈ 80 miles)
- Smaller, easy airport
- Often higher airfare
No matter which airport you choose, the scenic drive down the Overseas Highway sets the tone for your trip.
What the Keys Are Known For
- 🎣 World-class fishing (Islamorada is the “Sportfishing Capital of the World”)
- 🦞 Incredible fresh seafood
- 🍹 Waterfront happy hours
- 🌅Unreal sunsets
- 🏝 Island vibes — not manicured Caribbean beaches
You won’t find long stretches of white sandy beach here. What you will find are tiki bars, boat days, live music, and a pace that forces you to slow down.
Where to Stay
Sunset Inn

We’ve stayed here for the past six years, and it holds so many family memories.
- Heated saltwater pool
- Walkable to our favorite restaurants
- Quiet, tropical courtyard feel
What we don’t love? The price jump — from around $200 a night to nearly $800 a night. No thanks.
La Jolla Resort
Next year we’re planning to stay next door here. It has a similar Old Florida charm with a great waterfront location.
Vacation Rental
- A great option for families who want space + a kitchen
Where to Eat & Drink
We plan our Keys trips around food.

🐟 The Fish House
A must-stop in Key Largo on the drive down.
Fresh fish, casual vibes, and the perfect way to kick off vacation mode.
🍹 Lorelei Restaurant & Cabana Bar
Our #1 spot.
- Amazing happy hour
- Live music
- Sunset views
- Magician Michael Trixx (our kids LOVE him)
- And the best Key Lime Colada in the Keys
🌊 Lazy Days Restaurant
Great views. Great vibes. Fresh seafood right on the water.
🎣 Wahoo’s Bar & Grill
Perfect place to watch charter boats come in with the day’s catch.
🏝 Hideaway Cafe
Our favorite date-night spot.
It’s in Marathon — and absolutely worth the drive.
A mother-and-son team runs this cozy little gem, and the food is truly incredible. It’s intimate, romantic, and feels like one of those “how did we find this place?” restaurants you never forget. If you’re looking for a special night out away from the tiki-bar scene, this is it.
Breweries to Check Out
- Florida Keys Brewing Co.
- Islamorada Beer Company
Local beer + island air = perfection.
Things To Do
🐬 Theater of the Sea
A family favorite. You can:
- Swim with dolphins
- Meet sea lions
- Snorkel in a lagoon
- Watch marine animal shows
🐚 The Shell Shack
Souvenir heaven for shell lovers.
🐟 Robbie’s of Islamorada
Feed the tarpon right off the dock — a total must-do.
☀️ Islamorada Sandbar
Boat day essential. Anchor up, float, relax.
- Rent a boat
- Book a snorkeling tour
- Pull up to floating boat food trucks (!)
There’s nothing like standing in crystal-clear waist-deep water with music playing and boats all around you.
🏝 Bahia Honda State Park
If you’re looking for one of the most beautiful natural beaches in the Keys, this is it.
Clear water, soft sand (by Keys standards!), and incredible views of the old railroad bridge.
🌊 Sombrero Beach
One of the best public beaches in the Middle Keys.
Great for families, swimming, and sunset walks.
🌴 Founders Park Beach
A hidden gem in Islamorada.
Calm water, picnic areas, and a great option if you want a laid-back beach day close to town.
🤿 History of Diving Museum
We finally visited this on our last trip — and it was so much cooler than we expected.
This museum houses one of the world’s largest collections of diving equipment and artifacts, showcasing the evolution of underwater exploration from ancient times to modern scuba. You’ll see:
- Vintage dive helmets (including those massive old-school hard hats)
- Early underwater gear and air systems
- Rare artifacts and global diving history
- Interactive exhibits that explain how diving technology evolved
It’s part museum, part educational experience, and surprisingly fascinating — even for kids. If you’ve ever snorkeled, scuba dived, or just love ocean history, this stop gives you a whole new appreciation for what it takes to explore beneath the surface.
Definitely worth an hour or two, especially if you want a break from the sun.
Final Thoughts
The Florida Keys aren’t about luxury. They’re about memories.
Salt in your hair. Kids jumping in the pool. Live music at sunset. Fresh fish tacos. And one more Key Lime Colada before calling it a night.
If you love relaxed destinations with character, Islamorada will absolutely steal your heart.
Want More Trips Like This?
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