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 Catedral de San Cristobal in Old Havana was completed in 1777.

Don & Heidi Bucolo / Special to Cruiseable

Catedral de San Cristobal in Old Havana was completed in 1777.

Old Havana, Cuba: Walking tour highlights

Hemingway watering holes, 450-year-old buildings & other day-trip tips

Update: President Trump on June 16 left intact the fundamental elements of the Obama administration’s policy toward Cuba. The cruise lines have confirmed that cruises to Cuba will continue with no significant changes under the new guidelines. 
 

Now that major cruise lines have received permission to offer cruises to Havana, Cuba, from Florida, cruisers from the United States can explore this historic capital city, barring a change in policy from the Trump administration.

 
  DAY TRIPPING
 
What to do during your visit
 
 

We couldn't pass up the chance to be among the first travelers to visit this largest Caribbean island aboard Norwegian Sky in mid-May. During our first day in Havana, we spent most of the day exploring the historic streets of Old Havana.

Old Havana is a great walking city, and we managed to do everything by foot, partly with an organized “Walking Tour” excursion and some of it on our own. Here are the highlights.

 A fountain in Plaza de San Francisco in Old Havana.
Don & Heidi Bucolo / Special to Cruiseable A fountain in Plaza de San Francisco in Old Havana.

Admiring sculptures in Plaza de San Francisco

You can wander through most of Old Havana right from the cruise terminal. Unlike most cruise destinations, in Cuba you're required to have your passport on you, as you must go through Customs both when you disembark and when you return to the terminal to board the ship. When you start out, as soon as you exit the terminal, you're right in the middle of one of the city’s historic squares.

That's me with El Caballero de Paris sculpture. Rub it for luck!
Don & Heidi Bucolo / Special to CruiseableThat's me with El Caballero de Paris sculpture. Hold the fellow's beard and hand for good luck!

At the Plaza de San Francisco, you can get your first taste of what is in store for you as you explore the entire city, which is an UNESCO World Heritage site. Among the most noteworthy statues, the Lions Fountain, carved in Italy by Giuseppe Gaggini, was installed in 1836. A bronze statue, El Caballero de Paris, is a well-known attraction near the Basilica. José Ramón Villa Soberón sculpted it based on a ubiquitous street person in 1950s Havana, forever encapsulating the wanderer’s spirit. Travelers are said to have good fortune if they pose with the statue holding the gentleman’s beard and hand.

This is just one example of the mixture of culture and lore you will discover as you wander for the day throughout the cobblestone streets and alleyways. If you plan on touring the area on your own, we recommend downloading a map that does not require Internet access. Wi-Fi is spotty at best, and most of the landmark maps are in Spanish.

 El Templete, a monument that pays homage to the place where Havana's foundation was celebrated in 1519.
Stephen Colebourne / Creative Commons BY El Templete, a monument that pays homage to the place where Havana's foundation was celebrated in 1519.

450 years of history in Plaza de Armas

From Plaza de San Francisco, we continued our explorations in the oldest part of the city, Plaza de Armas. Dating back to the mid-1500s, this plaza is home to the birthplace of Havana. It is here that some of the most significant landmarks pay homage to the beginnings of the city. This includes the El Templete, a monument that pays homage to the place where the town's foundation was celebrated in 1519. The building is currently undergoing renovation.

Castillo de la Real Fuerza is a fort on the west side of Havana harbor bordering Plaza de Armas.
Wilder MendezCastillo de la Real Fuerza is a fort on the west side of Havana harbor bordering Plaza de Armas.

From there, you can’t help but be mesmerized by the impressive exterior and reinforcements of the Castillo de la Real Fuerza. The fort is now a museum open to the public and is considered the oldest stone fort in the Americas. It was a central battle station until later military installations were built across the bay.

Next door is a lush park. At the center is a statute of Carlos Manuel de Céspedes. The statue is a relatively new addition to the park, honoring the father of independence in Cuba.

The Hotel Ambos Mundos, where Ernest Hemingway began penning “For Whom the Bell Tolls” in 1939.
Don & Heidi Bucolo / Special to CruiseableThe Hotel Ambos Mundos, where Ernest Hemingway began penning “For Whom the Bell Tolls” in 1939.

As you proceed toward the next stop, make a slight detour a few blocks to the Hotel Ambos Mundos. For literary fans, this hotel holds specific importance as Ernest Hemingway's first residence in Cuba. His room, 511, is now a museum that can be toured and has remained largely unaltered since he lived there in the 1930s. Hemingway rented the room for $1.50 per night and began his novel “For Whom the Bell Tolls” here in 1939.

Plaza Vieja in Old Havana, Cuba, has been a gathering place for locals for centuries.
Courtesy of FathomPlaza Vieja in Old Havana, Cuba, has been a gathering place for locals for centuries.

Plaza de Catedral & Plaza Vieja

Next, head west a few blocks and you’ll come upon Plaza de Catedral. As the name suggests, this small plaza is home to the mesmerizing Catedral de San Cristobal (also known as the Cathedral of the Virgin Mary of the Immaculate Conception, pictured at top), an example of Cuban Baroque architecture completed in 1777 and reminiscent of centuries-old European cathedrals. Home to the Catholic archdioceses on the island, the church is open for touring and still holds mass. One of the smaller squares, it is surrounded by 18th century buildings housing museums, art galleries and restaurants.

As you stroll south, your eyes will be easily pulled toward the surrounding artists and small street vendors that line the more popular streets. Of course, there are also plenty of cafés lining the way with Cuban coffee and snacks if you’re looking for a break.

Plaza Vieja (“Old Square”), the last of the four main squares, is home to a local brewery located in one corner of the plaza. My wife and I made it a point to stop in for a few minutes to quench our thirst. This square is also home to cafes, a planetarium and a school nearby. Here you can relax, see kids playing football in the courtyard or admire the stained-glass windows adorning most second-floor buildings.

 Inside Bodeguita del Medio, a drinking spot and eatery that claims to be the birthplace of the mojito.
Don & Heidi Bucolo / Special to Cruiseable Inside Bodeguita del Medio, a drinking spot and eatery that claims to be the birthplace of the mojito.

Onward toward the Capitol & Central Havana

Beyond the city’s old squares, it is easy for travelers to find their way toward the center of the city, where the Capitol is located. During the roughly three-quarters of a mile walk toward Central Havana, we recommend a few brief detours. On the touristy side, there's La Bodeguita del Medio. The drinking spot claims to be the birthplace of the mojito — although this title is highly contested — and it was a longtime watering hole for prominent Cubans and visitors to the island. It’s a small place, and there’s always a line, but we couldn’t pass up the chance to grab a drink at the famous landmark.

 El Floridita Bar in Old Havana was a popular stomping ground for Ernest Hemingway.
Don & Heidi Bucolo / Special to Cruiseable El Floridita Bar in Old Havana was a popular stomping ground for Ernest Hemingway.

Speaking of drinks at famous landmarks, about three blocks from the Capitol you'll find El Floridita Bar (on Calle Obispo), a popular stomping ground for Ernest Hemingway (Papa got around!). No cruiser should pass up the chance to sample one of the proclaimed “best daiquiris” at this place. A life-size statue of the gregarious Hemingway stands guard over the corner of the bar as patrons file in and out for some daiquiris and live music.

The National Capitol Building in Havana was the seat of government in Cuba until after the Cuban Revolution in 1959.
Don & Heidi Bucolo / Special to CruiseableThe National Capitol Building in Havana was the seat of government in Cuba until after the Cuban Revolution in 1959.

In Central Havana, you can marvel at the pretty, iconic Capitol building (abandoned as the seat of government in 1959) and the Great Theater of Havana or grab a park bench in Parque Central and witness the clashing of new and old Havana. Still, the relics of days past are apparent with the 18th century buildings and 1950s classic cars.

 Museo de la Ciudad (City Museum) at Plaza de Armas is a must-see for history buffs.
Don & Heidi Bucolo / Special to Cruiseable Museo de la Ciudad (City Museum) at Plaza de Armas is a must-see for history buffs.

From the Malecon to artifacts of the revolution

For comrades who are still up for more exploring by foot, you can take the roughly half-mile walk to the Museum of the Revolution, the former presidential mansion that is now a museum. Under heavy armed security, the courtyard behind the museum houses the late Fidel Castro’s yacht, the Granma. As it was late in the afternoon by the time we arrived, we were not able to tour the museum or the nearby National Museum of Fine Art.

Even though our walking tour was coming to an end, there was still plenty to see, and after a night aboard Norwegian Sky we would return for another full day beyond the older city limits. Rum and cigar factories, the half-mile the Malecon (esplanade waterfront) and the modern neighborhoods of Havana were still waiting for us to explore. Accessible by taxi, these newer neighborhoods offer a greater glimpse into the people and society of Cuba in the 21st century.

Still, for those looking to continue on by foot, you can surely discover more hidden gems throughout the streets of Old Havana, where no taxi is need — just your sense of adventure.

How about you?

How about you? Have you visited Old Havana? Are you planning to visit any time soon? Or would you like to? Let us know in the comments! 

See our Havana travel guide for a list of cruise ships that call on Havana from Carnival, Norwegian Cruise Line, Royal Caribbean, MSC Cruises, Oceania, Regent Seven Seas, Azamara Club Cruises and others.

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DB & the Princess
Along with my wife, I'm the co-editor of EatSleepCruise.com, helping you sea the world, one port at a time!

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