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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

This walk is designed for Friday–Monday, because it begins with a tour of the Barnacle State Historic Site. Try to get there for the 10am tour, and notice the distinctive roof, which gives the house its name.

As you exit, turn left and go down to the corner of Devon Road to enjoy the Mission-style Plymouth Congregational Church , built in 1916. If they’re open, pop into the back gardens.

Now walk back along Main Highway several blocks to 3500, the Coconut Grove Playhouse , a handsome Mediterranean-Revival building that dominates the corner at Charles Avenue. Continue along Main Highway to the next street, then stop for lunch and some top-notch people-watching at the every-busy Green Street Café .

Afternoon

After lunch, walk up Commodore Plaza to visit 3168, the Midori Gallery . Afterwards, continue on to Grand Avenue and turn right; go down a couple of blocks to the major intersection and cross the street into the shopping mecca CocoWalk.

On the next block, Rice Street, look up to admire the fanciful façade of The Streets of Mayfair mall (see Hibiscus Hill, Out of Africa). To finish off your tour, visit Borders on the corner of Grand Avenue and Mary Street for a drink and maybe a book on Grove history.

Exhibit, Midori Gallery

Morning

Drive north from central Miami on Highway 1 (also called Biscayne Blvd). The road is lined with shops – stop off at any that catch your eye. Turn left on NE 163rd St, then right onto W Dixie Hwy (also NE 22nd Ave). The Ancient Spanish Monastery is on the right after the canal.

You may well feel a sense of awe as you walk around this beautiful little piece of medieval Europe on US soil. Even European visitors, who have visited many such buildings in their homeland, might still marvel at the dedication of Hearst to put it here.

For the best route through the grounds, start at the gift shop/museum, exit to the patio, through the gardens, cloisters, interior rooms, culminating with the chapel, and back through the gift shop.

Among the notable sights are an 800-year-old birdbath, a life-size statue of the Spanish king Alphonso VII (the monastery was constructed to commemorate one of his victories over the Moors), and two of only three known surviving round stained-glass windows from the 12th century.

Afternoon

In keeping with the Spanish-inspired theme, eat at nearby Paquito’s Mexican Restaurant and take a detour along NE 2nd Ave through colorful Little Haiti on your way back.

Mid-morning

First stop, if you like a cigar, is El Créditto (see El Créditto & El Créditto) on SW 11th Ave. Just a few doors along you’ll find the Botánica El Aguila Vidente . Let your eye wander over the shop’s plethora of paraphernalia, most of all the colorful plaster statues.

Next stop is at SW 13th Avenue, to pay your respects to fallen Cuban freedom fighters at the Brigade 2506 Memorial Eternal Flame (see The Brigade 2506 Memorial on Cuban Memorial Boulevard), before a sortie into the delightful fruit market at 1334, Los Pinareños Fruteria .

At the corner of SW 15th Ave, peek in on Domino Park where there’s always at least one game going on. And now comes time to stop for coffee and maybe a snack at the wonderful Exquisito (see Exquisito Restaurant). Try to grab one of the vibrantly colored tables outside.

Late morning

Continuing on to the next block, at 1652, take in the exciting Latin American art at the Agustín Gaínza Gallery , where you’re likely to meet the affable artist himself.

After that, try a free-form ramble of discovery – but don’t miss the gaudy entrance to La Casa de los Trucos , at 1343 – and when it’s time for lunch, head for El Pescador , also on the north side of Calle Ocho. This is the place to go for delicious fish.

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.

Morning

To get to the Charles Deering Estate , drive south from Miami on Hwy 1 (also called the Dixie Hwy) and turn left on SW 168th St. Follow it until it deadends at the Estate on SW 72nd Ave.

A full tour of the grounds will take 3–4 hours. Follow the Entrance Trail to begin, and as you emerge from the mangroves you will encounter a splendid vista of Biscayne Bay. Note the water level marker, showing the inundation caused by Hurricane Andrew.

Richmond Cottage, the original structure here, was built as an inn in 1896. It was destroyed by Andrew in 1992, but has since been replicated. The elegant Stone House next door contains bronze and copper doors, portraits of the Deering family, a celebrated wine cellar, and more besides.

Head over to the Carriage House, where you can see a vintage gas pump. If you have time, take the Main Nature Trail, which crosses a handsome coral rock bridge, built in 1918. Finally, walk out through the historic Main Entrance, with its coral rock pillars and wood and iron gates.

Afternoon

Picnicking on the grounds is a possibility, and some facilities are provided. Or, for an elegant lunch, head south to the Cauley Square Tea Room . To make a full day’s outing, head farther south along Hwy 1 to the eccentric Coral Castle .