Tackling the Four Squares of Old Havana, Cuba.

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Our exploration around Old Havana would have us exploring several of the cities four squares in this historic region. We’d explore these grand places with something to see around every turn. The surprise of such a European City in an island in the tropical Caribbean was a surprise to us all as we discovered something new.


This post is one chapter on our trip to the isolated country of Cuba. This trip was planned through Westjet Vacations. For more information on how this trip was booked, please see our trip introduction here. For other parts of the trip, please see this index.

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Activity: Tackling the Four Squares of Old Havana, Cuba.


We then wandered down past Hotel Los Frailes (The Friars) The property used to be a monastery, which has now been converted to a hotel. The property has an excellent location within Veija Havana and a stone’s throw from everything. It seems you can even book basic rooms ans suites on line for less than $200 USD in the summer. It’s not the Four Seasons, but I would easily make this a place to check into if I was wanting to stay in this immediate area on a freestyle trip. It won’t be at this price point for long.

The property has a resident quartet of instrument playing band members in the swish bar set on a backdrop of historic rooms.

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The Second Square: Plaza de San Francisco de Asis

We continued our walking tour to Plaza de San Francisco de Asis. The square initially contained a market in the 1500’s. It’s had a full restoration in the 1990’s. It featured the prominent Lonja de Commercio; a commodities market built in 1909 designed to house the foreign companies wishing to conduct business in Havana.

Our first visit in the square was to another statue, El Callabero de Paris; a well known street person who roamed through Havana in the 1950’s. The thing to do here is touch his arm and shoe based on all the wear marks.

We left Plaza de San Franciso de Asis and wandered up along the harbor towards the Plaza de Armas. Sadly, or fortunately depending on your perspective, the cruise ships had started to arrive in Havana, changing the visiting landscape forever.

The Third Square: The Plaza de Armas

The Plaza de Armas is Havana’s oldest square. It was laid out in the 1520’s. The site was initially used to conduct military exercises. Today’s plaza contains buildings from the 1700’s. It’s the home of the semi famous daily second hand book market, containing mostly writings about Che Guerra and other communist intellectual ideologies. I can’t think of any other second hand book markets that are of this size anywhere else.

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The Fourth Square: Plaza de la Catherdral

We wandered over to the last square of the day; Plaza de la Catherdral. There were several charming cafes on the walk over, with many of them playing life music. There were several quaint alleyways that enhanced the ambience of this old part of Havana.

The Plaza de la Cathedral is home to the Catherdral de San Cristobal de Habana and dates from the 1700’s. It’s the newest of the four squares at about 300 years old.

I took a look inside the Catherdral de San Cristobal de Habana. It was Italian designed and built between 1748 and 1767. The church became a cathedral which was one of the oldest in the Americas

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A Last Stop at La Bodeguita del Medio:

From the cathedral, we wandered up the street to the famous La Bodeguita del Medio. It is one of the most famous bar’s in Havana and has been frequented by Fidel Castro, Nat King Cole and Ernest Hemingway. It is reported to be the home of the mojito. There is even a signed inscription by Ernest Hemingway from his two favourite Havana bars. It’s a massive tourist spot now, but can you blame people for wanting the world’s most famous mojito?

We headed over to the waterfront, to get into our ride back to Varadero.

We headed straight back to the Ocean Varadero El Patriarca hotel after the day. It was exactly a two hour drive by van from Havana to Varadero with 130 km covered. The day of our Havana tour happened to be election day in the United States. We were a bit surprised, as was many, to see the results. It was interesting to see that there was CNN coverage in Cuba of the results. There wasn’t a lot of local public commentary on the results or open discussion about the matter among the Cuban’s that we interacted with on this trip. I suspect they were hopeful towards an opening of the borders to increase tourism but I would guess that the Trump Administration won’t be as quick to make this happen.

My Impressions of Walking in Old Havana:

Wow – there was much more to see in Havana than I initially expected. The city has yet to be discovered by tourists and there are many discoveries to be had around every corner. The city maintains a european feel to it which is a start contrast from the United States a short distance away.


If you’ve travelled to Havana’s squares, did you find it an enriching travel experience?

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