Joy Nulisch sits down with Rob Smith-Martin a lifelong Conch storyteller, musician, and entrepreneur to trace the version of the island many people only hear about in rumors: the 1970s and early 1980s, when storefronts were boarded up, rent was cheap, and artists, writers, and unforgettable characters filled the gaps. We talk about why that era felt like a “golden age,” how the Navy pullout and a shaky economy reshaped downtown, and what it meant to live in a place that still felt small enough for everyone to know your name.

We take the conversation across the water to Cuba, with Rob's firsthand experience visiting the island and working with Cuban artists. Rob shares what headlines miss, the warmth, generosity, music, family loyalty, and daily resilience that persist through shortages, outages, and political strain. We also revisit the Mariel boatlift and how it changed Key West schools almost overnight, pushing local kids to see a much bigger world. If you care about Cuban culture, Key West Cuban roots, and what real community looks like under pressure, this part hits hard.

Then we come back home for stories that feel like snapshots learning to swim at the Pier House pool, the nerves of swimming out to the harbor dock, and the way old Key West blurred the line between ordinary life and legend. We dig into the Key West Picture Show as a true time-capsule film, and we share a rare, personal look at Jimmy Buffett’s Key West connections, including how Sunshine, Rob's mom helped launch Margaritaville as a real mom and pop shop at the seaport before it became a global brand.

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