Old Havana Walking Tour

With two full days docked in Havana, Cuba, you are going to want to see as much as possible. On our four night Norwegian Sky Cuba cruise, our first pass at this port was an

Old Havana Walking Tour

With two full days docked in Havana, Cuba, you are going to want to see as much as possible. On our four night Norwegian Sky Cuba cruise, our first pass at this port was an Old Havana Walking Tour. As part of our shore excursion with Havana Journeys, we got a personalized guided tour of this UNESCO World Heritage site. With our knowledgeable guide, we traversed the cobblestone streets, exploring the city’s most notable landmarks. Along the way, we took a few detours to see some of the lesser known stops as our guide wanted to show us “the real Havana”. It was a tour we will surely never forget.

Shore Excursion Review: Old Havana Walking Tour

Docked in the Middle of All the Action

It dawns on you that Havana is unlike any other Caribbean port as soon as you exit the ship. With our passports and visas in hand, the customs and security process was a bit more intensive than other Caribbean ports, but luckily the process was orderly and efficient, and we were out of the terminal to officially set foot on Cuban soil in no time.

Exiting the terminal, it truly sinks in that you are in Old Havana as you peer across the street to Plaza de San Francisco. The square is home to the Basilica de San Francisco de Asis which was constructed in the early 17th century.

Old Havana Walking Tour ReviewOld Havana Walking Tour

It was here that we met our tour guide, Cathy. A lawyer and professor at the university, she was a wealth of information. Throughout the tour, she would instill historical facts and descriptions of the notable landmarks and areas of Old Havana, providing an eye-opening view into the lives of the Cuban people.

The Plaza de San Francisco is home to several notable sculptures and statues as well. Among them are the modern day Chopin statute (our official meeting point) and the Gentleman of Paris, the bronze statue by José Villa Soberón.  As Cathy described, visitors who pose with the statue of the city’s famous drifter are said to be granted good luck and fortune. Now that sounds pretty believable, right?

Old Havana Walking TourOld Havana Walking Tour

Exploring the Squares of Old Havana

As our launching point, we headed north from Plaza de San Fransisco to the oldest square, Plaza de Armas. Dating back almost 500 years, this early part of the city is now named for the military drills that were routine during the 17th century.  Just off the main park, you will find the Castillo de la Real Fuerza, considered the oldest stone fort in the Americas and now home to a replica of the famous weathervane depicting Havana’s only female governor. This star shaped fort offers tours during the day, so history buffs can see inside this impressive armament.

Old Havana Walking TourOld Havana Walking Tour

A small park is located across from fort. In the center of the lush park that is the heart of this plaza is the statue of Carlos Manuel de Céspedes, or the “Abraham Lincoln of Cuba” as our tour guide described him. After freeing the slaves that worked on his plantation, he initiated the uprising that called for Cuban independence from Spain. The statue is a 20th Century addition to the park replacing an early monument of King Ferdinand VII of Spain.

Also located in this plaza is arguably one of the most significant landmarks in all of Old Havana, El Templete. The small monument was constructed in the 19th century to commemorate the establishment of the city in 1519 at this location. Undergoing renovations while we were there, the monument holds a few important artifacts from the early city’s incorporation.

Old Havana Walking TourOld Havana Walking Tour

West of the park is the Museum of the City. Originally constructed as the Governor’s Palace, the building has served multiple municipality roles. This museum would make a great end (or beginning) to your historical step back into Old Havana. Take note of the wooden street located outside. It is said that the cobblestone was replaced by wood to reduce noise during the military exercises and allow the Governor to sleep.

Old Havana Walking TourOld Havana Walking Tour

Turning around, we crossed back through the Plaza de San Francisco onto the other squares of the City. Routinely, Cathy would make a quick detour for a few moments. Sometimes it was a short break to show us a few pieces of art from an up and coming artist or into a hotel or restaurant to see an example of the colonial style architecture.

Old Havana Walking TourOld Havana Walking Tour

A southward bound journey, we next arrived at Plaza Vieja, the “Old Square”, though not technically the oldest square.  Shops, cafes, and even a planetarium are among the square’s attractions. In addition, the southwest corner of the square is home to a brewery. A refreshing pint of local beer was not a bad way to cool off from a hot day exploring the city. Looking up, we couldn’t help but notice the intricate stained glass windows lining many of the square’s buildings.

Norwegian Sky Cuba Cruise Review

A more recent addition to the square is a statue of a woman riding a rooster. Symbolizing the changing power structure of a traditionally paternal people, the statue is just one of several notable works of 21st century art scattered throughout Old Havana.

It shouldn’t have been a surprise that as we were marveling at the surroundings, school children from the elementary school were moving between classes.  After all, this was just another day for the residents of Cuba. Following the crowds, Cathy guided us down a major street toward our next stop. Vendors selling local souvenirs, artists penning their latest creations, and musicians lined the streets. We couldn’t help but peak around the corners to see what was occurring down the various alleyways along the way.

Old Havana Walking TourOld Havana Walking Tour

We soon found ourselves in front of the Ambos Mundos Hotel, the first Cuban residence of Ernest Hemingway.  His room, 511, still stands largely intact as a museum. Here, tourists can see the lodging where this author called home during the early 1930’s. For us, a picture of the hotel sufficed.

Old Havana Walking TourOld Havana Walking Tour

A few quick turns from here, and we had entered the Plaza de Catedral. The centerpiece of this smaller square is the 18th century Baroque-style Cathedral. Originally started by the Jesuits, the sect was expelled from the island, and completion of the Cathedral fell upon other believers. Upon first glance, one may not notice that the two towers are not the same size. Due to a miscalculation in the area surrounding the church, the left side tower is thinner than the right tower.

Old Havana Walking TourOld Havana Walking Tour

This unique feature gives the Cathedral an even more awe-inspiring presence. Equally mesmerizing is the interior. An ornate design, it resembles the basilicas and churches found in Rome. Also take note of the structure immediately opposing the church. According to our guide, “some rich guy” built his palace in the middle of the street, blocking off the area.

A More “Modern” Havana

From here, we would come across one of the more notable “modern day” landmarks. The crowds had already gathered at La Bodeguita Del Medio, the supposed birthplace of the mojito. Perhaps a little too touristy for some, including our tour guide who indicated we could get much better drinks elsewhere. Later in the day, the Princess and I would return on our own for a mandatory drink. Still just as crowded as the morning stop, the bar had plenty of tourists coming and going having their fill of handmade mojitos.

Top Things to Do in Havana, Cuba on a CruiseOld Havana Walking Tour

As we continued onward, we were beginning to hit the more modern parts of the city. Approaching the Capitol, where Old Havana and “new” Havana collide, we took a quick pop into El Floridita. Known for being one of Ernest Hemingway’s favorite hangouts, you will find quite a few tourists ordering up the location’s signature daiquiris. The life-sized bronze statue of Hemingway beckons you to sit down and grab a drink. As you would expect, the Princess and I also headed back here later in the day for a round of this frozen treat after a long day of sightseeing.

Old Havana Walking TourOld Havana Walking Tour

Just a block from the bar is the Capitol. Across from Parque Central is also the Grand Theater of Havana and a line of 1950’s classic cars cruising the boulevard. We had managed to snake our way through the major squares of Old Havana, and we were now immersed in the city’s center, where both modern day Havana and its historic past collide. But, there was still plenty more to see in this capital city. For us, we would continue this journey, and our guided tour with Havana Journeys, via automobile. Stay tuned for part two of our tour coming soon.

Old Havana Walking Tour

Though very comprehensive, even this was not enough time to take in all of the heritage that lay at our cruise ship’s bow. Looks like we may need to add another Havana, Cuba cruise to our vacation list.

Are you ready to see Old Havana via cruise?


Have you toured the streets of Old Havana, Cuba? Do you plan on cruising to this largest Caribbean island in the near future? Drop us an anchor below to share your experiences cruising to Cuba.

Old Havana Walking Tour

Don Bucolo, or “DB”, loves everything about cruising- the ocean, the food, and the atmosphere. While he may be obsessed with doing extensive amounts of research on ships and all elements of a cruise, Don enjoys sharing his new found knowledge with fellow cruisers. When he is not sailing the high seas, he does whatever his wife tells him to do-it only took 10 years to realize this.
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  1. Amazing visit – looks incredible. We are going on the same ship next month. What did you do the second day and when did you return to the ship? it isn’t clear from the sky website when the ship departs the second day.