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Key West 2025-Trading Glitz and Glam for Flip Flops

Writer: Mandi CaseyMandi Casey

Key West is becoming more of my world than ever before. Another amazing week in our winter paradise, this place has slowly evolved from a simple getaway to a true retreat. Each year, the allure of glitz and glam fades further, replaced by the thrill of flip-flops, bike rides, and the salty air that gives me the same exhilaration I once found in the fast-paced rush of life. This year’s trip proved to be even more relaxing than the last. I suppose that happens with aging, but this is my first time here as a retiree!

I spent early mornings sipping coffee on the balcony, getting lost in a book as I watched the cruise ships arrive as the sun came up. In the evening, I’d sip wine while watching them depart, after cooling off in the pool and enjoying a late afternoon swim. The sense of peace I find here is indescribable.

Over the years, I’ve learned to appreciate the Key West treasures—nature, tranquility, history, and of course, Hemingway. But this year, I set out to explore something new: the Cuban influence. Key West is rich with Cuban heritage, seen in its vibrant culture, cuisine, and architecture. Its proximity to Cuba made it a gateway for immigrants, especially in the late 19th and early 20th centuries. The island’s Cuban roots are evident in its bustling cafes, cigar shops, and traditional dishes like ropa vieja and Cuban sandwiches. The colorful, pastel-colored homes and lively festivals reflect a unique fusion of Cuban and Floridian styles that define Key West’s charm.

The relaxation this year was immeasurable. In corporate America, an “out of office” email doesn’t mean much. You’re still expected to keep things moving, pushing projects forward, and preventing disasters, especially as customer support gets leaner each year. But this year I was truly able to unwind,  and did not have that daunting feeling on the last day, that I had to go back to a toxic work environment.

Each day began with long bike rides along the perfect, well-maintained paths by the beach. We’d end up at the historic wharf by lunchtime, where we’d stop for a bite. Afterward, it was off to Sloppy Joe's for some music and a Hemingway Mojito. The afternoons were spent lounging at the beach or by the pool, cooling off under the sun. We always had our Bluetooth speaker playing island tunes—Jimmy Buffet, Zac Brown, and the like. This year, a song by Zac Brown caught my attention:


‘It's my kind of medicine

Riden ' the blue where the world falls off

Swear I tried everything

But this kind of peace just can't be bought

The water is healing

It brings back the feeling I forgot

Like a child in the waves again

It’s my kind of medicine.’


Couldn’t have put it better myself.




 
 
 

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