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On March 21, 2016, Barack Obama, joined by the First Lady, will become the first US president to visit Cuba since the days of prohibition and Model T Fords. No doubt, his two-day itinerary will be jam-packed and heavily curated, but let’s just imagine he gets a chance to give his Secret Service detail the slip and wander around incognito.

Where could he explore in a country that has long been off-limits to most Americans?

Capitolio Nacional

The Obamas might enjoy time dwelling upon the similarities rather than the differences between the US and Cuba outside Havana’s magnificent Capitolio, a close copy of Washington’s Capitol building. The Capitolio is currently undergoing a lengthy renovation and is covered in scaffold, but there’s no mistaking its elegant neoclassical façade completed in the late 1920s (the last time a US president visited Cuba!). In a park nearby, there’s a statue of one of Obama’s predecessors, Abraham Lincoln, a rarity in Cuba.

El Capitolio peeks through a gap in the winding streets of Havana © Halbag / CC BY 2.0 El Capitolio peeks through a gap in the winding streets of Havana © Halbag / CC BY 2.0

Hotel Nacional

One of Havana’s finest hotels, and an unusual cocktail of art deco, neoclassical and eclectic architecture, the Hotel Nacional is a piece of Cuban history and a grandiose reminder of an era when Americans practically ran the city. The President and the First Lady could sip mojitos on the breezy garden-terrace, admire the tiled Moorish lobby, or explore corridors still haunted by the ghosts of Winston Churchill, Frank Sinatra and Lucky Luciano. Facing the ocean outside is a rare but poignant US-era monument dedicated to 260 servicemen killed in the explosion of the battleship USS Maine in Havana harbor in 1898. The incident was a pivotal moment in Cuban history and sparked the Spanish-American war.

Finca Vigía

US writer and long-time Cuba-phile Ernest Hemingway is the second most revered Ernesto in Cuba after Che Guevara, and his erstwhile house, perched on a hill in a suburb of Havana, is one of the city’s best museums. Obama – himself a published author – could admire shelves stacked with literary tomes; peruse the writer’s cherished boat, Pilar; and view the swimming pool where Ava Gardner once swam naked. Should this whet his appetite for more Papa-themed memorabilia, Havana tour agencies can organize plenty of Hemingway excursions.

Hemingway's writing desk at Finca Vigía © Bruce Tuten/CC BY 2.0 Hemingway’s writing desk at Finca Vigía © Bruce Tuten / CC BY 2.0

Private dining

The biggest revolution in Cuba these days has nothing to do with socialismo and everything to do with food. One of the most positive results of Raúl Castro’s 2011 reforms is the growth of private enterprise, particularly in the culinary sphere. Havana’s once dire restaurant scene is positively thriving and has reawakened interest in Cuba’s long underrated comida criolla. We recommend the President books a table at Doña Eutimia for an authentic plate of ropa vieja (spicy beef stew).

Habana Vieja

The renovation of Havana’s old colonial quarter is one of Cuba’s biggest success stories, but one that is little discussed in the US. The Obamas could get the lowdown on this against-the-odds rehabilitation by undertaking a tour with the City Historian’s Office. Scholarly guides will explain how tourist dollars are used to finance meticulous historical preservation and kick-start crucial social projects for Havana’s struggling neighborhoods.

Colorful colonial buildings in Habana Vieja © Roberto Machado Noa/Getty Images Colorful colonial buildings in Habana Vieja © Roberto Machado Noa / Getty Images

Callejón de Hamel

Obama, like many Cubans, has a strong African heritage and he’d definitely appreciate this colorfully painted back alley that acts as a nexus for Havana’s Afro-Cuban community. Adorned with outlandish public art and mysterious relics to religions of African origin, the Callejón is best visited on Sundays around noon when a posse of rumba drummers lays down intricate rhythms.

Malecón

Should they successfully shake off their minders, the Obamas could attempt to get a glimpse of the real, uncensored Cuba on Havana’s wave-lashed seawall where hundreds of ordinary Habaneros come to stroll at sunset. The 8km-long Malecón is a quintessential Havana experience, a giant outdoor living room packed with fishers, lovers, musicians, joggers, jokers and dreamy Florida-gazers. Even hardened Cuba-cynics have been known to be ensnared by the intrigue and romance.

Two men fish off of the malecón © Sarah Morgan/Getty Images The malecón is a popular spot for fishing © Sarah Morgan / Getty Images

Fábrica de Arte Cubano

Contemporary news stories often predict the impending Americanization of Cuba, largely ignoring the potency of the nation’s local culture. Left to explore Havana’s cultural crevices on their own, the Obamas could lend an ear to what young Cuban artists, musicians and thinkers have to say at this innovative new art collective. The Fábrica de Arte Cubano – which hosts music, dance, film, painting and sculpture – isn’t a standard gawp-at-the-exhibits gallery-performance space. Instead, in the true spirit of Cuba’s non-celebrity culture, visitors are encouraged to mingle with the artists and add thoughts and ideas of their own to the creative canvas. 

Baseball

Sport is a great cultural leveler, and Americans and Cubans share an unquenchable passion for baseball. Obama is, allegedly, a Chicago White Sox fan, but he’d need to temporarily switch loyalties to Los Industriales if he wanted to ingratiate himself to the baseball fanatics of Havana who spend most of their non-game time discussing form in a section of Parque Central called Esquina Caliente (hot corner). The home-side, nicknamed the Leones Azules (blue lions), play at the slightly down-at-heel Estadio Latinoamernicano. While the facilities aren’t exactly on a par with the Yankee stadium, the talent on the pitch could give any US professional team a run for its money.

Las Terrazas

Two days, doesn’t leave much time for side-trips, but, in a perfect world, the President and First Lady would escape the hullabaloo of Havana and hire an antediluvian ‘yank tank’ to drive them 55km west, to the tranquil eco-village of Las Terrazas. This successful environmental reclamation project which has reinvigorated a section of denuded forest by planting trees on terraced slopes is now a Unesco Biosphere Reserve stuffed with abundant birdlife. It would be of special interest to a president who has regularly spoken out on environmental matters.

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