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Much has changed since Ernest Hemingway’s days in Old Havana, the glamour times of 50s Americana. But in essence, the enclave of colonial decay remains the same: stunning, vibrant, mysterious. Deemed a UNESCO World Heritage Site since 1982, Havana Vieja, as Cubans call it, is indisputably so, the number one reason that brings tourists to Cuba. Once the playground of the rich and famous is at it again, more alluring than ever. Following extensive restoration efforts in the past decade, Old Havana shines ever more brightly. 

Founded in 1515 by Spanish conqueror Diego Velázquez, the old city is bordered by El Malecón, the famed five-mile long boulevard that runs along the waterfront. Built to protect the city from the fury of its crashing waves, a long stroll - or better yet, a cruise along the promenade in a brightly colored Buick or Chevy – is a must before entering the historic center.

El Malecón bordering Old Havana

Easily explored by foot, the island’s star attraction delights with ornate facades, palatial cathedrals, lively plazas and the everyday, Cuban hubbub. Walking through decades of revived colonial splendor, Cuba’s most riveting outdoor museum unravels. With styles ranging from Baroque, Art Nouveau, Moorish and Neo-Classical, the architectural spectacle is eclectic and complete. With every step, cobblestone streets give way to a rainbow of color, and life: street musicians, cigar vendors, inviting paladares. Inside hotel stunners like Hotel Raquel, Florida or Sevilla, all-marble lobbies tell tales of a faded glory. At Bodeguida del Medio, Hemingway is still sipping his made-famous mojito propped at the bar, a blast from the past incarnated in a life-sized bronze statue.

Hotel Sevilla looking down on the National Ballet School Havana Vieja

Whichever way you take it, Old Havana is a pleasure to explore. To start with, head to Plaza Vieja, the most popular gathering spot, for a mirage of yellows and blues, Spanish arches and fine stained glass windows. To follow, marvel at the magnificent façade of Catedral de San Cristobal, namesake for Plaza de la Catedral. A striking example of Cuban Baroque architecture dating from the eighteenth century, step inside to observe the vaulted ceilings and the statue of St Christopher.

Plaza Vieja Havana Vieja

Catedral de San Cristóbal de La Habana Havana Vieja

On your way to Plaza de Armas, perhaps Old Havana’s most expansive square, veer unto Calle Obispo, known cross-country for its vibrant nightlife, effervescent atmosphere, and the famed Hemingway daiquiris at El Floridita. When in doubt, simply pause to soak it all in, a scene sought after by millions worldwide.

But in fact, in true Cuban spirit, Old Havana’s life spills out into the street. It’s the narrow alleyways with laundry strung through, the sounds of salsa and son, children roaring through the gutters. Take a chance to get lost. Peek inside a courtyard, or two. Step inside the real Havana. The treasures you’ll find are yours to keep.

Visit Old Havana on all of insightCuba's Cuba Tours. 

Written by Monica Suma
Photos by Robin Thom

Monica Suma is a freelance travel writer. Follow her on Twitter @monicasuma.