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Explore the oldest parts of Havana, as we walk back in time more than 500 years to the city’s founding.

Explore a labyrinth of cobblestone streets during a privately-guided walking tour of Havana’s city-center, La Habana Vieja. Founded in 1512, we’ll visit some of Old Havana’s most important sites: the Plaza de Armas, Plaza de San Francisco, Plaza de Cathedral, Plaza Vieja, San Francisco de la Havana. Expect more than a few surprises along the way at this UNESCO World Heritage Site.

We’ll also interact with small business owners along Calle Obispo. As we shop local food, books, and art, we’ll learn about Cuba’s dual-sector economy, in which private and government-owned businesses operate.

This activity is available on our Undiscovered Cuba, Legendary Cuba, Classic Cuba, and Weekend in Havana tours or can be integrated into a custom-made itinerary. 

Old Havana, Cuba is a must-see for any visitor. As you tour the cobblestone streets of Habana Vieja, look for these historic spots.

The Oldest Things You’ll See in Old Havana, Cuba

Old Havana, Cuba is just two square miles, but packed with weeks worth of attractions. Whether on your own or with a guided walking tour, look for these landmark locations in Habana Vieja.

The Oldest Streets in Havana

In the early 1500s, Havana numbered four streets, and Calle de Los Oficios was chief among them. Lined with cobblestone and 18th-century facades,  it’s not as busy as some nearby lanes – but at nearly 500 years old is the closest you’ll get to where Havana began. For more hustle, take Los Oficios to Calle de Los Mercaderes. There you’ll find Havana’s burgeoning class of small businesses, keeping true to its name as the street of merchants. 

Los Oficios connects to the equally old Calle Obispo, a narrow street designed to protect passerby from the sun – and the site of an original city gate past the walls of Old Havana. From there, you can cross Avenue del Puerto and walk Havana’s most iconic avenue, the Malecón.

The Oldest City Square in Havana

Havana’s oldest streets lead to the 16th-century Plaza de Armas or “square of arms.” The city’s first public square gained its current name for its use as a military parade ground under Spanish rule. The space centers around a statue of Carlos Manuel de Céspedes, a native of Bayamo and the father of Cuban independence. 

Old Havana’s three 17th-century plazas aren’t far away. Plaza de la Catedral, once known as “Swamp Square” for its muddy terrain is home to the main conduit of Old Havana’s oldest aqueduct, as well as the area’s oldest house – Casa del Conde de Casa Bayona, circa 1720. Plaza Vieja, formerly known as “Plaza Nueva,” was built as an alternative to Plaza de Armas. Today, it’s home to some of Havana’s best architecture. And finally, there’s Plaza de San Francisco, which takes its name from the Franciscan convent built there in 1591. 

The Oldest Hotel in Cuba 

Hotel Inglaterra ranks high among Cuba’s many historic hotels. First opened in 1875, it played host to José Martí, Anna Pavlova, Winston Churchill – and now to countless American visitors as one of few US-owned hotels in Cuba. In 1879, writer José Martí gave a speech here advocating for Cuban independence from Spain, which came less than 20 years later. Across from Hotel Inglaterra, you’ll find a marble statue of the writer, which is thought to be the oldest statue of the Martí in Cuba.

Next door you’ll find El Capitolio, a magnificent landmark from the time between Cuban Independence and the Cuban Revolution.

The Oldest Stone Fort in the Americas

Completed in 1577, the Castle of the Royal Force or Castillo de la Real Fuerza is a massive fortress framed with 30-foot tall limestone walls. An engineering marvel built by slave labor over twenty years, it was designed by the Spanish to fend off pirate attacks – but was later found ineffective due to its location inside the bay. Today, it’s the oldest stone fort in the Americas and part of the UNESCO World Heritage Site in Havana.

Along the nearby Malecón, you’ll find another fortress, Castillo San Salvador de la Punta. At night, a gigantic chain used to span from La Punta to a castle on the other side of the bay – the colonial equivalent of a “we’re closed” sign. 

The Oldest Daquiri in the World

Among the oldest still-operating bars in Havana, El Floridita is the birthplace of the frozen daiquiri as perfected by Constantino Ribalaigua Vert. Of course, the bar’s most notable occupant was Ernest Hemmingway. And he’s still there – memorialized in a bronze statue at the end of the bar. The feeling of pre-revolution Cuba is alive and well here, complete with bartenders in red coats. 

Questions about Old Havana, Cuba or ready to book a trip? Text or call an insightCuba Travel Specialist now at 1-800-450-CUBA (2822).

Ryan Walker is a travel expert and creator of TheGayTripper.com