The sun rises over Miami as your day begins with a hotel pickup, rolling southward along the scenic Overseas Highway toward Key West. This four-hour journey threads through the Florida Keys, each island a stepping stone over crystalline waters. Arriving in Key West, the town greets you with its colorful, Caribbean-inflected streets where artists display their crafts, and open-air cafés hum with the scent of salt air and freshly brewed coffee. Historical markers like the Hemingway House anchor the island’s narrative, inviting a brief respite before the main event.