For those of us who have been in the cruise industry for a long time, Cuba has always been a place to cruise by or around. The big mountainous blob of land that stays in your vision for hours. I honestly never thought I would see the day that we would cruise right into Havana. There were more than a few misty eyes onboard when we did just that on December 26.

Cuba Cruise -arriving Havana

We didn’t want to wait any longer to go to Cuba. Personally, I wanted to see Cuba while it was still an authentic experience. We found exactly that – but for how long that will last is anyone’s guess. My first recommendation: Go now – don’t wait!

Celestyal Crystal: Our Ship in Cuba

We chose all-inclusive Celestyal Crystal, which turned out to be just what we were looking for. This 476-cabin vessel cruises from Montego Bay, Jamaica and completely circles the island of Cuba in 7 days, stops in 3-4 ports, and includes 2 full days in Havana.

The cruise line arranged our Cuban visas, and they also include shore excursions in the price of the cruise to U.S. citizens to comply with the Cuban government’s “People to People” program. (However, if you – like us – want to set out on your own, it’s not prevented, and we had total freedom to explore on our own… as long as we had our visas and passports with us.)

Cuba cruise - waiter on Celestyal CrystalCelestyal markets this cruise as an authentic Cuban experience, and it did not disappoint! They (uniquely) hire Cuban staff in critical front-line positions and tailor the food and entertainment on board to Cuban heritage. We felt immersed in the culture – from music to food and the arts – both ashore and on board ship.

The relatively small number of passengers reminded us of cruising 30 years ago – lots of smiles and no stress embarking or disembarking.

And one of the biggest delights every night: Getting close to the ocean and watching the sunset from the bar on deck 5 – close enough to feel the sea mist. 

On our cruise, we visited 3 cities – Santiago, Havana, and Cienfuegos. Note: The Isle of Youth was intended as a 4th destination, but the government is concerned about the sensitivity of the environment and stopped cruise ship calls for the time being. We didn’t mind, because we were rewarded with even more time in Havana!

Day 1 – 2: Montego Bay to Santiago de Cuba

Our first stop was Santiago de Cuba,  where Fidel Castro was born and interred recently.  Much of the “revolutionary city” consists of cold war buildings, and the area is surrounded by mountains – the same mountains where Fidel Castro hid and plotted his revolution.

It was here where Castro made his famous “History will Absolve Me” speech which became the platform of the Cuban Revolution. It is steeped in history and well worth the visit. We were lucky that it was the first stop on our itinerary – and all agreed that it was the right place to begin our Cuban journey.

One thing we can give the revolution credit for (sadly a backhanded compliment) is the outstanding preservation of the culture, which includes their buildings. There are a number of Unesco sites across the island, and it’s money from Unesco and the resulting tourism that allows for the continued restoration.

Cuba is, without a doubt, the best example of cultural preservation that I have ever seen in my 40 years of travel around the globe. It is a living, breathing museum where people live, go to school, grow their families, take care of their elderly, and nurture their culture through their art, music and beliefs.

Santiago is also the center of dance, and we were treated to a performance of Afro-Cuban dance. We found that they respect the African culture and acknowledge the part that the original slave population brought to Cuba. Santiago, on the southwest corner of the island, is closer to the Dominican Republic and Haiti, than Havana, which has shaped the city’s distinct identity. The one thing that struck us all (my family & friends who joined us), was the variety of ports and how unique every experience was – each one brought Cuba alive for us – in distinctly different ways.

Day 3: Christmas at Sea

We celebrated Christmas on board ship during our first day at sea. The ship was dressed with decorations, including a couple of impressive gingerbread houses. Christmas carols were sung by the entertainment staff and everyone on board got into the spirit.

We had our own family tradition and enjoyed our shipboard celebration.

Day 4 & 5: Havana

My first impression – color… lots of it! I somehow had it in my head that it would be dreary or dilapidated. We arrived with the sun at dawn, which lit up the beautiful buildings on the waterfront.

From the moment that I set eyes on the Malecon, I got a wave of nostalgia that never let up the entire time we were there. It brought back memories of car trips in the 50’s in the old purple Chevy, and a throwback to a more genial time – slower, more deliberate, and somehow richer.

The port is smack in the middle of Havana Vieja (Old Havana). The first thing you see as you exit the terminal is a boulevard teeming with 1950’s era cars. It makes you smile and breathe and know that you are here.

Across the terminal is a square with cobblestone walking streets jutting off in every direction. Take your pick – architecture, museums, historic squares, cathedrals, bookstores, and eateries. It would take days to get around and weeks to see it properly – so it’s best to read up in advance and make some choices. And that’s just within walking distance!

Currently, only 25% of Old Havana is restored and you can see restoration projects everywhere. It’s a feeling of an ongoing long-term project, done in an unhurried manner – not at all the frenetic pace of development seen in China or other developing nations.

As you walk the streets, it becomes routine to step around cement bags and construction materials, but it’s also an invitation to poke your head inside to glimpse the restoration process. Compare these with the completed projects that are adorned with colorful facades and gorgeous soaring courtyards, filled with gardens and artwork. You can only imagine how much more beautiful it will become over the years.

Music wafts out of almost every corner – live music, not recorded – from an array of artists, young and old. The word “eclectic” is used a lot to describe the culture, the artwork, the music, and especially the museums. There is a museum to pay homage to almost everything in Havana, and they are each charming and quirky – not slick and obsessively curated. While guidebooks post an entrance fee of 1-2 CUC’s (on par with the US Dollar). we found that few museums collected it and if they did, they called it a “donation”.

We found the Museo de Naipes (playing cards), which turned out to have an impressive selection of hand painted tarot cards; and the African house, which displayed artifacts from the era of slavery and an exhibit on the Santeria religion.

Other museums included a museum of arms, photography, religion, fire equipment, automotives, rum, tobacco, currency, a silver museum (opening soon); and our favorite, the museo del chocolate (!), which is really more of a café than a museum – dishing our delectable chocolate goodies along with the history of chocolate in Cuba.

Did you know that the first and only electric railway in Cuba was built in 1917 by none other than the Hershey Chocolate Company? The train still runs today from Havana to Matanzas – where the original chocolate plantations were located. You can spend 4 hours on this train traveling the scenic countryside from Havana to Mantanza and return for about 3 CUC’s ($3 US).

To really enjoy Havana, it is best to let go of any preconceived notion of time. You are on Cuban time now and expecting something to happen because a guidebook says so will only end in disappointment. The same goes for restaurants. They will likely not have your selection, so don’t get too attached to the menu. It’s impressive to see how well the locals let things slide off their shoulders, with a smile.

The Cuban people have no expectations – and just shrug it off. We saw no displays of anger or irritation – and they have no particular desire to see the same in visitors to their country. So have patience, grasshopper – stand in lines and learn to enjoy it. You will ultimately be rewarded by the best ice cream you’ve ever tasted or hot churros with chocolate and cinnamon. Some things are worth waiting for.

After a day in Havana, it’s possible to feel the lessening of the stress and burden we brought with us, and slow down to Cuban time… the time of Mohitos and mambo.

This goes for the cruise ship terminal, too. Two ships are all the terminal can handle right now and it stresses their security capability when two are in port. So if another ship is in port and you have tour plans or dinner plans, it’s best to get off the ship early to avoid getting caught in a line. Good news is that there is an efficient cambio in the terminal to exchange money.

Bring a lot of cash – US, Canadian, Euros. Do not expect to be able to use American credit cards anywhere in Cuba – at least not today. And negotiate your taxi fare BEFORE you step into the car – especially the best restored classic cars.

A trip down the Malecon in a convertible is a must! We stopped at the Hotel National for a Mojito, which turned out to be an inspired choice. They have an al fresco bar on the waterfront and it’s the perfect way to enjoy this mafia-era grand hotel where Myra Lansky and his cronies partied with Frank Sinatra in the 50’s.

That was how we ended our stay in Havana, as we made our way back to the ship for a 9:30 pm sailing.

Day 6: Day at Sea

The next day was at sea, which was a good time to reflect on all that we saw and experienced in Havana. What a luxury to have a breather in between.

Our next and final stop – colonial Cienfuegos, Perla del Sur (Pearl of the South).

Day 7: Cienfuegos

Cienfuegos is located on the country’s most spectacular bay. It was initially settled by the French, which accounts for the interesting architecture, including their own Arco de Triunfo.

In 2005, this city was designated a World Heritage Site by Unesco, who brought in the funds to restore many magnificent buildings including the Teatro Tomas Terry, a landmark opera house that has witnessed performances by Enrico Caruso and Anna Pavolova.

After roaming around the historic square, we jumped in a 1950’s taxi and traveled down their Malecon to Punta Gorda, to see the mansions that were built by the sugar plantation barons of the past. Many of these are now restored bodegas or casa particulars (B&B’s) – colorful, whimsical, and for rent for the equivalent of $40 a room!

On the way back to town, we paid homage to the statue of Benny Moré (above right), the Nat King Cole of Cuba, who was born in Cienfuegos. Every other year, this community hosts a Benny Moré jazz festival… hmm, those $40 rooms are looking very appealing for a return visit.

Day 8: Montego Bay

So – it’s time to get back to Jamaica and return home. One last pleasant surprise was how easy and comfortable the debarkation process was on the Celestyal Crystal. (By the way, Celestyal also allows passengers to board in Havana and take the cruise round trip Havana.) Given that Montego Bay was a port stop for some, they allowed us to stay on board as long as we wanted. Our flights were not until 4 pm, so we checked out of our rooms after breakfast, but stayed on board reading and relaxing until after lunch. What a luxury!

In conclusion, I recommend seeing Cuba by ship, especially if the itinerary gives you as much time ashore as we had. It was truly memorable and inspired us all to revisit as soon as we can.

What would we do with more time in Cuba? Take a bike tour through the old tobacco plantations in Valle de Vinales; dive in the clearest waters in the Caribbean in the Archipielago de los Canarreos, climb Pico Turquino in the Sierra Maestra, ramble through scenic Trinidad and Camaguey on foot. I think I just started a love affair with a country.

Yo soy Cuba.