Convertible Cruisin’ & Island Vibes: A Florida Keys Escape You’ll Never Forget

By Jani Aylsworth-Gunter, Take Time To Travel


The Florida Keys …just drive!

There’s just something about the Florida Keys that hits different. It’s like the second you leave Miami behind and hit the road with the top down (because yes, you’re definitely renting a convertible or a Jeep for this one), your blood pressure drops and your vacation soul takes over.

Let me walk you through one of my favorite tropical escapes—perfect for couples, a girls’ trip, or just anyone in need of some sun, salt air, and that laid-back island magic.

Miami and the Seven Mile Bridge!

Fly into Miami, Baby

Book an early morning flight into Miami and waste no time. Grab your bags, pick up your ride (go convertible if you’re feeling a little glam, Jeep if you’re feeling a little wild), and hit the road headed south on the legendary Overseas Highway.

This isn’t just a drive, y’all. It’s an experience.

Picture this: turquoise water on both sides, palm trees dancing in the wind, and the Seven Mile Bridge stretching out in front of you like something out of a movie. Don’t rush it. Stop for photos, a key lime slushie, or just to take in the views.

Isla Bella Beach Resort Feels Like Heaven!

Marathon: Mid-Key Magic

Your first stop? Isla Bella Beach Resort in Marathon.

This place is absolutely stunning. Think swaying hammocks, private balconies, and the kind of pool that makes you want to cancel all your plans and just lounge. But you won’t, because there’s plenty to see and do here.

Snorkeling …and Christ of The Abyss

Things to do in Marathon:

• Turtle Hospital – A must-do for animal lovers! Learn how they rescue and rehab sea turtles.

• Sunset Cruise – I can help you book one with champagne and all the island vibes.

• Sombrero Beach – A local favorite. Pack a picnic and soak up the sun.

Where to eat:

• Burdines Waterfront – A casual marina spot with killer hush puppies and fried key lime pie. (Yes. Fried. Key. Lime. Pie.)

• Hideaway Café – More upscale, romantic, and tucked away. A total hidden gem.

Key West is Quirky …and so much fun!

Key West: Quirky, Cool, and So Full of Life

After a few nights in Marathon, it’s time to make your way down to the end of the road—literally. Welcome to Key West, where the roosters run wild and the good times never stop.

Check into the Casa Marina Key West, Curio Collection by Hilton—a beachfront beauty with old-school charm and that perfect location just steps from the action but still serene enough to hear the ocean.

Things to do in Key West:

• Hemingway Home & Museum – Come for the history, stay for the six-toed cats.

• Southernmost Point – Snap that iconic photo. Touristy? Yes. Worth it? Also yes.

• Duval Street – Bars, boutiques, drag shows, galleries… it’s everything and then some.

• Sunset at Mallory Square – Street performers, snacks, and a view that’ll knock your flip-flops off.

Places to eat & sip:

• Blue Heaven – Outdoor, funky, and full of personality (and chickens). Get the banana pancakes or shrimp & grits.

• Latitudes on Sunset Key – You’ll need a boat ride to get there (included with your res!), but this romantic spot is top-notch.

• El Siboney – Authentic Cuban food in a no-frills setting. So good.

The Hemingway House and those Cats w/ 6-toed Murder Mittens!

Wrap It All Up in Style

After soaking up all that sunshine, seafood, and sweet island living, return your rental car at the Key West Airport and hop on your flight home, sun-kissed and soul-happy.

Let Me Plan Your Keys Escape!

I’ll handle all the logistics—flights, cars, resorts, excursions, and restaurant recs. You just pack your sunnies and your sense of adventure.

Life is one big journey—and I’m sharing mine, one mile and one moment at a time. Subscribe to follow along.

Ready to feel that island breeze in your hair? Let’s make it happen.

– Jani, your go-to gal at Take Time To Travel, 770-334-2256


The Take Time To Travel Team – Cindy, Jani, Tammy, Trisha, Krystal

Life is one big journey—and I’m sharing mine, one mile and one moment at a time. Subscribe to follow along.

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