Havana, Then and Now

Havana’s buildings crumble under the weight of 500 years of history. Its cobble-stone streets have withstood the boots of imperial soldiers, vagrant pirates, gold-laden merchants, gangsters, militant police, and guerilla revolutionaries. Travelers meandering through the city will experience the pages of history books come alive as they encounter centuries-old fortresses, dignified colonial mansions, prohibition-era hot spots, and retrofitted American classics. This is, after all, one of the oldest cities in the Western Hemisphere.


The Spanish founded the city of San Cristobal de la Habana in 1515, and the original city walls surround Old Havana (La Habana Vieja) to this day. The most prominent port in the Caribbean for over 200 years, Havana’s initial populace was comprised primarily of sailors, merchants, and crooks—a hot spot for taverns, brothels, and gambling houses. Throughout its time under Spanish rule, Havana was the meeting place for the Spanish treasure fleet’s annual voyage across the Atlantic. Loaded with gold, silver, and other riches from the New World, hundreds of ships gathered in Havana Bay before setting sail under navy protection. This yearly gathering positioned Havana as a major target for the marauding pirates of the Caribbean, and the city was burned down and pillaged on several occasions.

The Piazza at Havana circa 1762 | by Dominic Serres

In an attempt to combat these attacks, the Spanish built several substantial stone fortresses (some of the oldest in the Americas) that still stand today. The star-shaped, Renaissance-style Castillo de la Real Fuerza is located in Old Havana, adjacent to the Plaza de la Catedral (Cathedral Square). The castle’s drawbridge and thick limestone walls evoke a medieval spirit, and the bell tower is topped with a weather-vane in the shape of a woman (la Giraldilla) who today serves as the face of Havana Club rum. Across the bay, the thick stonewalls of El Morro Castle were built into rocks rising up from the sea. The massive fort was Havana’s strongest defense, and today is home to a comprehensive museum and some of the best views of the city.

  The Capture of Havana, 1762: The Morro Castle and the Boom Defense Before the Attack |  by Dominic Serres

The Capture of Havana, 1762: The Morro Castle and the Boom Defense Before the Attack | by Dominic Serres

In 1762, the British successfully invaded the supposedly impenetrable fortress and took control of Spain’s most important port for a brief 12-month period. When the Treaty of Paris was signed in 1763, Spain regained control of Havana, but the momentary change in rule made a significant impact on the city’s culture. While the British were in control, trade routes between North America and other English colonies were opened, and Cuba saw an influx in horses, material goods, and slaves, prompting both an architectural and agricultural boom.

Once the Spanish regained control, sustained development continued on the island, and throughout the 19th century, businesses from the United States began to form, with a vested economic interest in Cuba’s future. In 1898, on a friendly visit to Havana, the battleship USS Maine exploded inside of Havana harbor, prompting the U.S. to lend support to Cuba in their fight for independence from Spain. The U.S. subsequently won the Spanish-American war and occupied Cuba until 1902.

 El Hotel Nacional

El Hotel Nacional

Throughout the first half of the 20th century, U.S. influence in Havana was prominent. Hotels, restaurants, nightclubs, casinos, and golf clubs littered the city, which, only a short boat ride away, acted as a playground for wealthy Americans and celebrities like Frank Sinatra and Ava Gardner.
Havana’s bustling nightlife didn’t only attract stars. U.S. gangsters saw a potential to make big bucks in a city slowly adopting the title of “Latin Las Vegas.” When Fulgencio Batista initially took power in the 1930s, he had strong ties to American interests, most noteworthy of which was his close friendship with Meyer Lansky, one of America’s most powerful gangsters. In 1946, the opulent Hotel Nacional, on the edge of Havana’s Vedado neighborhood, was the site of the historic “Havana Conference,” a gathering of crime families led by Lucky Luciano (who was living illegally in Havana at the time) to hammer out details of a national syndicate. Rumor has it that plans to assassinate mobster Bugsy Siegel were devised at the top floor of the hotel.

Fritz Gordon, Al Capone and Julio Morales, Mayor of Havana | Cuba, 1930

While Americans basked in Havana’s frivolous high life, Batista brutally ruled over Cuba. After six years of bloody combat between guerilla revolutionaries and Batista’s military police, Fidel Castro rode into Havana on a jeep in 1959 celebrating the success of the revolution. Shortly thereafter, in 1962, came the U.S. trade embargo, cutting off much of the tourism and commerce that breathed life into Havana.

Beautiful residential building in Havana — the city is filled with historical architecture

From the grandeur of crumbling marble stairways to the sounds of street vendors selling peanuts, Havana’s 500 year history is palpable throughout all facets of life in this great city.

Over the past two decades, there has been a notable focus on restoration to preserve Havana’s unique history and iconic status.

The Old Havana city center was declared a UNESCO World Heritage site in 1982, and restoration projects, including the ongoing restoration of the former capitol building (El Capitolio), proliferate the area. Walking the streets of Old Havana, as streetlamps cast a romantic glow, sounds of live music and banter fill the air, and classic automobiles idle by, it isn’t hard to imagine yourself transported to the magic of a bygone era.

El Capitolio under restoration | Habana Vieja (Old Havana)