Vedado, with its sprawling layout, sumptuous mansions, and sense of 1950s middle-class Havana arrested, couldn’t be more different from Habana Vieja or Centro Habana. While Old Havana is bursting at the seams with cobbled plazas and narrow streets fringed by museums and stunning colonial architecture that demand one’s attention non-stop, Vedado exudes an aura of cosmopolitan mid-20th century elegance. And if Habana Vieja is arguably the ‘soul’ of Havana, Vedado is undisputably the vibrant heart, including as the main center of commerce, government, and nightlife.

Originally an area of dense woods and limestone hillocks, in the 17th-century El Vedado (meaning “the forbidden zone”) became a military area closed to civilians and development as a defensive zone against any attach on Habana Vieja. The restriction was lifted in 1858 and a layout approved for an orderly grid arrangement of broad tree-lined streets separated at regular intervals by spacious parks and double-width Parisian-style boulevards oriented northwest-southeast (and perpendicular) to channel the ocean breezes.

Following the brief Spanish-American-Cuban War (1898) development began in earnest as U.S. investors poured in money, while the ‘Dance of the Millions’ sugar boom fostered an explosion in Cuba’s own monied class. Vedadoexpanded rapidly, becoming a showpiece of eclectic architecture. A leisurely stroll down any street is a magical mystery tour of architectonics, with stunning exemplars of everything from neo-classical and Italian Renaissance to Art Deco and Modernist styles. The latter includes avant-garde rascacielos (skyscrapers) that recall the mid-1950s mobster heyday, when laundered Mafia profits metamorphosed into the ritziest high-rise hotels outside Las Vegas.

The hilltop Hotel Habana Libre (formerly the Havana Hilton), Meyer Lansky’s ultra swank 21-story Hotel Riviera, and Mobster boss Santo Traficante’s Hotel Capri (the first hotel to have a rooftop swimming pool) are steeped in Mafia memories. Most of pre-revolutionary Havana’s big hotel casinos were here (the Capri’s casino was famously fronted by Hollywood actor/gangster icon George Raft). So, too, the brash nightclubs of Havana’s famously risque entertainment district at the base of La Rampa (Calle 23). The latter still buzz today: A testament, with their original 1950s signage, to the ill-fated Batista-mobster marriage. Everything changed in January 1959 when Fidel Castro rolled into town with his army of scruffy bearded rebels and set up his initial HQ on the 24th floor of the then spanking new Havana Hilton, just steps from the University of Havana—a magnificent neoclassical complex—where Fidel studied law.

A neighborhood within the municipality of Plaza de la Revolution, Vedado sprawls west to the Río Almendares and south into the more modern (and hillier and rambling) Nuevo Vedado and the vast Plaza de la Revolución itself. The setting for most central government buildings and for major rallies and events, the plaza is a de rigueur venue to visit. Nearby, the magnificent Cementerio Colón is not to be missed. Nor the grandiose Hotel Nacional and, nearby, Coppelia—the world’s largest ice cream store and another shrine to Modernist architecture. In fact, Vedado is studded with sites of interest. Plus, its leafy residential pockets are studded with myriad theaters, nightspots, and restaurants, including many of Havana’s top paladares.

La RampaLa Rampa

The University & aroundThe University & around

Along the MalecónAlong the Malecón

Calle Línea & aroundCalle Línea & around

Central VedadoCentral Vedado

Calle 23 & aroundCalle 23 & around

Plaza de la RevoluciónPlaza de la Revolución

Nuevo VedadoNuevo Vedado