The landmark Hotel Nacional (Calles O y 21, tel. 07/836-3564) is dramatically perched atop a small cliff at the junction of La Rampa and the Malecón. Now a national monument, Hotel Nacional was designed by the same architects who designed The Breakers in Palm Beach, which it closely resembles. It opened on December 30, 1930, in the midst of the Great Depression.

In 1933, army officers loyal to Machado holed up here following Batista’s coup; a gun battle ensued. More famously, in December 1946 Lucky Luciano called a mobster summit (ostensibly they were here to honor Frank Sinatra) to discuss carving up Havana.

The elaborately detailed, Spanish-style neoclassical hotel was greatly in need of refurbishment when, in 1955, mobster Meyer Lansky persuaded General Batista to let him build a grand casino and convert some of the rooms to luxurious suites for wealthy gamblers.

Luminaries from Winston Churchill and the Prince of Wales to Marlon Brando have laid their heads here, as attested by the photos in the lobby bar. It is still the preferred hotel for visiting bigwigs.

Beyond the Palladian porch, the vestibule is lavishly adorned with Mudejar patterned tiles. The sweeping palm-shaded lawns to the rear—the terrace bar is a de rigueur spot to enjoy a mojito and cigar—slope toward the Malecón, above which sits a battery of cannons from the Wars of Independence. The cliff is riddled with defensive tunnels built since the 1970s.

The Edificio Cuervo Rubio (Calles 21 y O), cater-corner to the hotel entrance, is an art deco stunner. Nip inside the lobby, which has an Italian marble statue, and look up through the “tube” of the spiral staircase augering up seven flights. The modernist Hotel Capri (Calles 21 y N) was built in 1958 by the American gangster Santo Trafficante and was a setting in the movie The Godfather. At last visit it was a shell awaiting restoration.