Miami is a matrix of man-made islands, causeways, and paved-over Everglades that has gotten by on a desirable climate, a thriving pan-Caribbean culture, and some of our nation’s finest hucksterism. Born as a high-class playground—the original polo fields are now golf courses—Miami first boomed at the beginning of the 20th century. Wondering how to attract vacationers and residents to a place without a history, Miami’s developers lit upon a grand idea: Build the place like it had one. Mediterranean revival abounds, Spanish colonial holds court, and swimming pools are cut to look more like Pompeii than Palm Beach. Even the oranges were imports, cultivated to convince railroad baron Henry Flagler to extend the rails all the way to Florida’s tip.

Cathy Leff, director of Miami Beach’s Wolfsonian–Florida International University Museum, loves Miami in part for all its flashy invention. But she says that big bucks and big construction are adding some serious substance to her subtropical city. Miami was, and for some still is, a winter destination, but this current boom is about more than just another faux-Deco hotel.

The city of Miami, located on the Florida mainland, sprawls inland from its downtown waterfront as city neighborhoods eventually bleed into the first ring of suburbs. The more urban Miami Beach is actually a separate city. Just one of the many islands in Biscayne Bay, it is connected to the mainland by a web of causeways and is home to some of Miami’s most fabulous hotels, Art Deco architecture, and beaches.

Defying conventional Miami wisdom, and its prestige-loving car culture, Leff convinced us to join her on a two-day bike tour exploring the city streets, galleries, delicious dives, one-stop Haitian voodoo shops, and even a night club still bumping at nearly noon (we’re 99 percent sure we spotted Vanilla Ice). We covered 40 miles and 11 islands, and used up an entire tube of sunblock.

What are your favorite buildings here?

One of my favorites is the Bacardi Building north of downtown Miami, at Biscayne and Northeast 21st. Bacardi has always realized the power of architecture in branding both a product and a company. They have built great buildings in Havana and Santiago also. The Bacardi Building is the best example of the International Style meets the subtropics.

And the famous Art Deco hotels?

The “famous” buildings are the authentic Art Deco buildings, the Art Deco historic district, and what we call MiMo (Miami Modern). I’m a modernist and a preservationist, and I believe we should protect the buildings of the past, but new architecture should reflect our own times and aspirations. The good is that the change we are now starting to see is the recognition that contemporary architecture really can be compatible within a historic district. I think architecture has been (and will continue to be) less successful when we have tried to emulate or reinvent the past, and Miami definitely has its fair share of faux Art Deco and Mediterranean revival architecture. But I do love the real deal like the Fontainebleau and Eden Roc hotels on Collins Avenue in South Beach, both by Morris Lapidus. Miami has some funny moving architecture—the cruise ships that come into town. My apartment overlooks the Port of Miami, and I love getting up early on Saturday and Sunday to watch the cruise ships—or horizontal skyscrapers—as they arrive, completely dominating the downtown landscape. They are great visual additions to the skyline and contribute to the excitement of this growing urban activity.

The sandwich I had at Enriqueta’s was great. I’d love to eat my way through Miami.

Enriqueta’s is a delicious little Cuban spot just north of downtown, and just one of hundreds of small, fun, and mostly family-run restaurants. A great way to experience Miami’s cultural diversity is through its culinary culture. We have incredible Cuban, Nicaraguan, Peruvian, Brazilian, and Argentine food.

The Cuban influence on Miami is well-documented, but the Little Haiti neighborhood struck me as pretty vibrant itself.

Miami is such an extraordinary confluence of cultures, but sometimes you have to get out of South Beach to see it. By exploring the neighborhoods and the specialty shops within them, you learn so much. about the cultures that populate the city. The botanicas in Little Haiti, the heart of which is around Northeast Second and 54th Street, are just an example for getting a sense of the rich Haitian culture here. I’ve collected religious objects, so I love shops where you get the saints right alongside the Haitian voodoo.

The Wynwood neighborhood and the Design District in Miami are hot spots for contemporary art. What should we see?

The Rubell and Margulies collections are great in Wynwood, as is the Bakehouse Art Complex, Emmanuel Perrotin Gallery, Rocket Projects, and MOCA at Goldman Warehouse. Try Placemaker and the Moore Space in the Design District. I also like the Fred Snitzer and Bernice Steinbaum galleries.

Miami is a pretty young city. It didn’t really take off until the 20th century.

Though we have the oldest European settlements in the U.S., the state only took form when Henry Flagler extended the railroad to Miami in 1896. Florida understood the need to promote the state’s image to lure tourists and investors. This can be seen in the invention of new architectural styles that communicated centuries-old appeal in then-new cities like Coral Gables or Palm Beach, or through the images the state exported at the 1933 and 1939 World’s Fairs. They came, they built, and they are still coming. But this time there is substance behind the images.