Cruise to Havana, Cuba on Norwegian Sky

In October of 2018, Connor and I went on the Norwegian Sky 4-day cruise from Miami for a stop at Norwegian’s private island and an overnight stop in Havana, Cuba. It was an incredible experience, one that was only heightened by the fact that the entire ship was Open Bar, meaning that everyone was drinking pretty much all the time.
We boarded in Miami, and, since we were there before the rooms were done, went straight to the buffet and got drinks from the pool bar. I was thrilled to find they had an entire slushy machine full of Frozé (aka Frozen Rosé), also known as the drink of my dreams. I probably had about 10 cups of this throughout the cruise.

The view of Port of Miami.

Like any Norwegian cruise, there were lots of activities, from themed trivia to game shows to performances in the main theater. Our personal favorite was the man at the piano bar; he led the crowd in various popular songs, engaging with everyone in the room, even those that just walked in for a moment to get a drink.

One of the trivia games we attended.
A fun competition-style singing show on the ship.

Our first stop was Great Stirrup Cay, Norwegian’s private island in the Bahamas. Our plan was to get there first thing in the morning, stay for the island lunch, and return to the ship before the afternoon rush. As we crossed in the tender boat to check out the island, we were a bit surprised at how choppy it was, but overall we made it there safely. Unfortunately, the captain was concerned about the choppiness, and so they made us all evacuate the island about 15 minutes after we arrived. But I got a solid 15 minutes of sunbathing and at least got to see everything, which seemed awesome!

A view from the beach.
The picture we got as we were leaving!
The tender boat we took back. Incoming storm in the background.

Fortunately, the storm cleared up by the next day, when we arrived at our real destination – Havana, Cuba! We spent the day walking around and exploring, taking in all the main sights.

Havana architecture.
La Catedral de la Virgen María de la Concepción Inmaculada de La Habana
The Cuban flag.
Plaza de la Revolución.
We are so sweaty!

We ended up skipping on a walking tour we had planned because of how hot and humid it was (we’re West Coast weaklings), and relaxed back on the ship. But that night we had our most exciting plans – dinner and the show at Cafe Tropicana! The Tropicana is an 80-year-old cabaret-style show with dancing, singing, and so much drinking. We opted not to go with the ship, so instead of taking a bus, we hailed a cab, a Pontiac straight from the 50s. Our driver pointed out some of the neighborhoods around town and told us about how he had fixed up the car with parts from California, where I’m from!

Us with our cab, picture taken by our awesome driver!

As seasoned cruisers, we knew better than to book with the ship and instead booked on our own through the Cafe Tropicana website. This way, we spent about half as much, got a three-course meal, got front row seats at a table literally right next to the stage (at one point I climbed onto the table to get onto the stage, that’s how close it was), and essentially bottomless Cuban rum. I’m tellin you, we got to the table, there was us, two other girls from the cruise, and one girl from Peru. They set down one bottle of rum and we each got a can of soda, and we assumed that was it. We started splitting the rum, and 15 minutes later, they set down a second bottle of rum! We thought great, one for each side of the table – and then they set down another bottle of rum! So yes, we definitely got toasty, and yes, we definitely had leftover rum at the end.

The appetizer at dinner.
Dancing Queen!
Young and sweet!
Having the time of our lives!

The show itself was amazing, full of elaborate costumes, dozens of performers, awesome solos, and finished off with the dancers bringing audience members onstage to dance with them – guess who was the first one up there? I danced up there for what felt like an hour, and probably was. It currently ranks as the coolest experience of my life – dancing along to moves led by the Cuban performers alongside audience members from around the world, all of whom were having the time of their lives, despite many of us not speaking the same language. It was an example of the universality of dance. At one point, it started to rain, and we were all led off the stage, until it stopped moments later, and everyone rushed back on. After dancing, we offered the remaining rum to our new friend from Peru, who spoke little English, and we little Spanish, and I found myself knowing a lot more Spanish under the influence of rum than I did when I was completely sober. The coolest part of the conversation is when we realized that she had family in Cupertino, about 15 minutes away from where I grew up.

Overall, it was an incredible experience, one that brought together groups from all walks of life, and I’m so glad we went by ourselves, because apparently the cruise ship passengers had to leave immediately when the show ended. Fortunately for us, our cab driver waited until we were done partying, brought us safely home, and we went back to the ship around 1 or 2 am.

Our farewell to Havana.
Of course a towel turtle!

We bid farewell to Cuba, slept in the next day, and pretty much relaxed around the ship as we sailed back to Florida. It was a wonderful trip, full of great interactions with fun fellow passengers (probably encouraged by the open bar), and it was amazing to get to explore Cuba after years of a travel boycott. I would definitely recommend this cruise, possibly more than any other one of done, simply because of how affordable it was and the value that you get, in both on-ship and off-ship experiences!

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2 thoughts on “Cruise to Havana, Cuba on Norwegian Sky”

  1. Dear penelopeburgess, I am cruising on the Norwegian Sky to Havana in April. It is a bit unclear if I can leave the ship on my own to rent a car and have me driven around by a guide. Could you advise how you went about Havana without booking an excursion

    • Hi Charlotte, I had this exact same question before I went! The cruise companies make it sound like you have to book through them to even get onto the island, but it is surprisingly easy to get a Visa for just walking around. When you apply for the Visa (I did this through the ship), select “Support for the Cuban people” as your reason for visit, and as long as you do something in Havana that supports Cuban citizens, you’re good to go. Technically you are supposed to keep a record of what you do as it could be questioned for two years, but I’ve never heard of anyone being asked about their trip.

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