On December 17, 2014, Barack Obama and Raúl Castro announced the start of normalizing Cuba-US relations. At that very moment, we were wandering the streets of Havana, unaware of this historic day due to the lack of internet. The latter is just one of the many consequences of an economic embargo and communist rule for half a century. It is what makes Havana a city like no other, breathing history but longing for a future.
#1- Trade local tips for a cocktail
The limited tourists in Havana are welcomed with open arms, ready to take you on a tour of the city. After just a couple of hours, we started seeing a trend. The history lessons by helpful citizens would always end in a bar, with a cocktail on us. Luckily, a cocktail in Havana doesn’t break the bank, with delicious mojito’s for just three dollars. A small price to pay for a local take on Cuban history and culture. We put a halt to the spontaneous tours on day two, as we were not making it past Havana’s bar scene.
#2- Ride an old-school taxi
Classic American cars from the 1950s and before are an integral part of Havana’s street scene. The first part of the 20th century saw a big inflow of American cars into Cuba. After the Cuban revolution, Fidel Castro put an import ban on foreign cars and car parts. As a result, Cubans cherished their American cars and held them together with any part they could find. A lot of these cars have been turned into improvised taxis, often shared by locals in Havana. It’s not until you take a ride that the effects of time become clear. Brace yourself, cause classic cars do not have seat belts and Cubans drive as swiftly as they dance casino.
#3- Drink on Ernest Hemingway’s triangle
Ernest Hemingway sure knew how to pick his literary retreats. After spending various winters in Key West, Florida, Hemingway started looking for inspiration in the streets – and bars – of Havana. His first home in Cuba was Hotel Ambos Mundos, where he rented a room for seven years. Eighty years later, the pink hotel’s charm is still intact. The rooftop bar offers great views of Old Havana and the harbor. From the hotel, Hemingway could walk to his two favorite watering holes: La Bodeguita del Medio and El Floridita. The former claims to be the birthplace of the mojito, the latter the cradle of daiquiri.
#4- Take a bus to the beach
The Cuban capital has its own riviera. Playas Del Este is a strip of paradise east of Havana. It can be reached by a short bus ride from the historic city center. There are six beaches to pick from, each a world apart from their neighbors in Varadero. The lack of luxury resorts around Playas del Este means little tourists and more locals enjoying a day off. Santa Maria del Mar is considered the main beach of Playas del Este. Local vendors prepare mojitos, piña coladas and simple meals right on the beach. My fifth mojito of the day was even served with a wedding proposal.
#5- Explore four colonial plazas
Old Havana counts four beautiful colonial plazas. Just a short walk apart, all squares can easily be explored in one day. Here they are ranked from old to new, with their main function back in the day.
Plaza de Armas | Military
Plaza de Armas is Havana’s oldest square, built shortly after the city’s foundation in 1519. Its name stems from the military exercises that used to be carried out from the square. Visit the fort Castillo de Real Fuerza, or stroll around the daily secondhand book market.
Plaza de San Francisco | Commercial
Housing the former stock exchange and customs building, Plaza de San Francisco was always commercial in nature. The traffic caused by the adjacent port led to the emergence of a market.When the monks of the San Francisco basilica complained about the noise, a new square was built to accommodate the market: the Plaza Nueva was born.
Plaza Vieja | Residential
Plaza Vieja was initially called Plaza Nueva, built to accommodate the merchants banned from Plaza de San Francisco. Sadly enough, part of the original Plaza Vieja was demolished to make space for an underground parking garage. Thanks to a big restoration project initiated by UNESCO, the Plaza Vieja looks better than ever. It is the only square that houses a variety of bars and restaurants, which instantly makes it my favorite.
Plaza de la Cathedral | Religious
If you can’t walk past a church without entering – talking to you dad – this is the square for you. The impressive baroque Cathedral de San Cristobal lends its name to the youngest square of Habana Vieja.
#6- Revel in fifties glamour
Old Havana showcases the city’s rich colonial past, but Vedado reminds of Havana’s recent glory days. In the decennia before the revolution, American investors turned Vedado into a mixture of glamour and gangster. Luxurious hotels and casinos arose everywhere, financed by the mob and encouraged by the Cuban government. The gangsters and casinos are long gone, but part of the glamour stood the test of time. The best proof of that is Hotel Nacional, Vedado’s art deco landmark. Enjoy a cocktail on the back patio with a view of El Malecón.
#7- Trace the roots of Cuban cigars
The Viñales Valley was named UNESCO world heritage for its cultural value and dramatic landscape. Here, tobacco is still produced the traditional way. Animals are used for ploughing the land and tobacco leaves are harvested by hand. These methods produce the finest tobacco of the country, and by extension, the world. The valley is characterized by mogotes, limestone hills that arise abruptly from an otherwise flat surface. Make the three-hour trip from Havana to experience the making of world-class cigars; the spectacular landscape is a bonus.
#8- Stroll along the city’s bustling veins
Two bustling boulevards make up the heart of Havana. One of them is Paseo del Prado, a dividing line between Old and Central Havana. This elegant boulevard is flanked by trees and static buildings, reminding of promenades in Southern Europe.
Locals and tourists love promenading along El Malecón, a five-mile-long strip separating the city from the Atlantic ocean. Just 220 miles apart, the resemblance to Miami’s Ocean Drive is undeniable.
#9- Stand on the Cuban side of the revolution
The Museo de la Revolución is housed in the old presidential palace and a must-visit on a trip to Havana. It tells the story of the revolution from a Cuban perspective, which is not easy to come by in Western countries. An important landmark in this story is La Cabaña, a massive fort east of Havana. In the years after the revolution, the fort served as a military prison. It was here that Che Guevara oversaw hundreds of executions. If not for the bloody history, go for the stunning sunset views of Havana and El Malecón.
#10- Walk the line between glory and decay
Havana’s colorful streets make up much of the city’s charm. Beautiful art deco and colonial buildings line the streets. But the colorful facades are deceiving. Rooftops reveal a different Havana, one that was heavily impacted by fifty years of communist rule and economic embargo. Tourism can act as an economic engine for the country, so one can only hope that Cuba-US relations continue to warm up.