10 Must-Try Experiences in the Florida Keys This Week 🌴

Dear Road Trippers,

Living in the Florida Keys isn’t just about sunshine and saltwater—it’s about the little moments that make this place feel like paradise every single day. Whether it’s grabbing a bite at a favorite local haunt, catching the sunset from a hidden spot only the locals know, or wandering off the beaten path to discover something new, the Keys are always surprising me.

This week, I’ve rounded up some of my favorite experiences happening right now, along with a few hidden gems I love sharing with friends (and now, you!). So, whether you’re planning a visit or you’re lucky enough to call the Keys home, let’s dive in.

1. Sunset Celebration at Mallory Square (Key West)

📍 Location: 400 Wall St, Key West, FL
🌐 Website: Mallory Square Sunset Celebration

Why You Should Go:
You can’t live in the Keys and not be mesmerized by the sunsets—every single one is different, and Mallory Square is the quintessential spot to soak it all in. The energy here is infectious, with street performers juggling fire, local artists selling their crafts, and, of course, the blazing sky stealing the show. Even as a local, I never tire of it.

👉 Pro Tip: Arrive at least 45 minutes early, grab a mojito from a nearby vendor, and don’t leave without trying a piece of freshly made Key Lime Pie on a stick.

2. Dive into History at Pigeon Key (Near Marathon)

📍 Location: MM 47, Old Seven Mile Bridge, Marathon, FL
🌐 Website: Pigeon Key Foundation

Why You Should Go:
I can’t count the number of times I’ve walked the Old Seven Mile Bridge to Pigeon Key, and it never gets old. The views alone are worth it—miles of sparkling water in every direction. But stepping onto this little island, with its quaint historic buildings and peaceful vibe, feels like traveling back in time. It’s the kind of spot where you can leave the modern world behind, even if it’s just for an afternoon.

👉 Pro Tip: Bring a picnic lunch and spend a few hours here exploring the island—it’s one of the most peaceful places in the Keys.

3. Sample Local Flavor at Hogfish Bar & Grill (Stock Island)

📍 Location: 6810 Front St, Stock Island, FL
🌐 Website: hogfishbar.com

Why You Should Go:
This is where I take out-of-towners when I want to give them a real taste of the Keys. It’s not fancy—it’s authentic. Picture picnic tables by the dock, boats coming and going, and locals laughing over cold beers. The Hogfish Sandwich is the star here, but honestly, everything on the menu is incredible.

👉 Pro Tip: Go for lunch or an early dinner—parking can get tricky during peak times.

4. Explore the Mangroves on a Kayak Tour (Lower Keys)

📍 Location: Multiple Launch Sites Throughout the Keys
🌐 Website: Keys Kayak Tours

Why You Should Go:
When I need to clear my head, I grab a kayak and head for the mangroves. There’s nothing like paddling through these quiet, winding tunnels, surrounded by nature and the occasional curious heron or manatee. It’s peaceful, it’s beautiful, and it always reminds me why I love living here.

👉 Pro Tip: Bring a dry bag for your phone—you’ll want to snap a few pictures but keep it safe from splashes.

5. Treat Yourself at Kermit’s Key Lime Shoppe (Key West)

📍 Location: 200 Elizabeth St, Key West, FL
🌐 Website: keylimeshop.com

Why You Should Go:
I stop here more than I should probably admit. It’s the ultimate one-stop-shop for all things Key Lime, and their frozen Key Lime Pie on a stick is dangerously addictive. If you’re lucky, you might even catch Kermit himself waving to customers.

👉 Pro Tip: Take home a bottle of their Key Lime BBQ Sauce—it’s a game-changer for grilled seafood.

6. Relax at Bahia Honda State Park (Big Pine Key)

📍 Location: 36850 Overseas Hwy, Big Pine Key, FL
🌐 Website: floridastateparks.org

Why You Should Go:
Bahia Honda isn’t just a beach—it’s one of the most stunning spots in the Keys. When friends visit, this is where I bring them for clear, turquoise waters and soft, sandy shores. Whether I’m snorkeling, reading a book, or just taking in the view, it feels like a vacation every time.

👉 Pro Tip: Snag a spot early—it’s popular for a reason, and the best spots fill up quickly.

7. Visit the Turtle Hospital (Marathon)

📍 Location: 2396 Overseas Hwy, Marathon, FL
🌐 Website: turtlehospital.org

Why You Should Go:
This place has my heart. Seeing the amazing work they do to rescue and rehabilitate injured turtles is so inspiring. Every visit reminds me how important it is to protect the unique wildlife that makes the Keys so special.

👉 Pro Tip: Book your tour in advance—they fill up fast, especially on weekends.

8. Experience the Quirkiness of Robbie’s Marina (Islamorada)

📍 Location: 77522 Overseas Hwy, Islamorada, FL
🌐 Website: robbies.com

Why You Should Go:
Robbie’s isn’t just a stop—it’s an experience. Feeding the massive tarpon is a must, but the open-air market and waterfront bar are just as fun. I’ve spent entire afternoons here, sipping cocktails and browsing the quirky handmade goods from local vendors.

👉 Pro Tip: Try the conch fritters while you’re there—they’re some of the best in the Keys.

9. Stroll the Key West Historic Seaport

📍 Location: 201 William St, Key West, FL
🌐 Website: keywesthistoricseaport.com

Why You Should Go:
This is my favorite spot to wander on a quiet morning. The boats, the salty breeze, the friendly locals—it’s the heart of Key West. Stop by Schooner Wharf Bar for live music or grab a Cuban coffee at one of the nearby cafés.

👉 Pro Tip: If you’re here during the holidays, check out the festive lights and the famous “Crab Trap Christmas Tree.”

10. Celebrate with a Sunset Sail (Key West)

📍 Location: Multiple Operators at Key West Harbor
🌐 Website: Fury Cat

Why You Should Go:
No matter how many sunsets I’ve seen, a sunset sail always feels magical. The colors, the breeze, the sound of the waves—it’s pure perfection.

👉 Pro Tip: Go with a small operator for a more intimate experience. Champagne toasts included!

What’s Your Favorite Keys Spot?

Have you ever stumbled upon a hidden gem or taken a detour that turned into the highlight of your trip? Reply to this email and share your story—I’d love to feature it in a future edition!

Here’s to sunsets, seafood, and the beauty of the journey,
Brian

Florida Keys Road Trip Team

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