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Morning
Begin at about 10am. Start at the Southermost Point in the continental US, overlooking the Atlantic at the intersection of Whitehead and South Streets, where the marker informs you that Cuba is only 90 miles (144 km) away. Then head up Whitehead to the Lighthouse Museum and climb its 88 steps for a great overview of the island and beyond.
Next stop is Hemingway House, at 907; here you can take in a nostalgic trip through the writer’s life as a Conch. Then move on to the Green Parrot Bar, at 601 Whitehead, to admire its age-old funkiness and have a drink before lunch. From here, head over to Duval Street, to Mangoes Restaurant, at 700, for a great lunch and equally stellar people-watching.
Afternoon
Afterwards, take a look at the Spanish Colonial façade of the San Carlos Opera House, and, on the next block up, the stainedglass windows of St. Paul’s Episcopal Church. At 322, pay a visit to the Wreckers’ Museum.
Now things might get very “Key West,” as you climb to the third floor of The Bull at 224 to find The Garden of Eden and see who’s sunning themselves in this clothing-optional bar.
Farther along, stop at historic Sloppy Joe’s bar. By now, it should be time for the famous sunset celebration, so head to Mallory Square and add your positive energy to the festivities!
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