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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!

Morning

From the southern end of the District on Ocean Drive, at 6th Street, head northward, checking out not just the façades but also as many of the hotel interiors as you can. Many have unique design elements in the lobbies, bars, and gardens.

Between the Leslie and the Cardozo is the wonderful Carlyle, currently undergoing a major restoration.

Turn left after the Cavalier, and go to the next street over, Collins Avenue. Turn right on Collins and check out Hoffman’s Cafeteria at 1450, built in curved Nautical style in 1939 by Henry Hohauser. Stop here for lunch.

Mid-afternoon

A little farther on, you’ll find the St. Moritz Hotel, which features a cut coral façade and neon.

At 1685, you can’t miss the all-white Delano, with its landmark winged tower. The outlandish post-modern interiors are by Philippe Starke, and contain original Dali and Gaudi furniture.

Next stop is the Ritz Plaza, with another fantasy tower in glass block. When you get to 21st St, turn left; on the next corner you will encounter the Abbey Hotel, with its marvelous salamander motif and Flash Gordon-style towers.

Head back to Collins Ave, and at 1775 you’ll find The Raleigh Hotel – it’s a beautiful location for drinks.