My Top Ten Experiences in Cuba

Traveling in Cuba wasn’t all introspection about tourism and musing on economics – no, we definitely had a lot of fun on our people-to-people tour as well. We crammed a lot in our eight brief days on the island, but I’ve narrowed it down to my top ten experiences in Cuba.

1. Touring Old Havana

To be clear, all of Havana is old. Due to lack of resources and materials, there are few buildings built after the 60s. Many buildings are in terrible condition for the same reason. Luckily, a significant amount of money has been poured into Old Havana (especially with visit of the Pope), and the colonial architecture has been gorgeously restored.

And then, sometimes our guide would take us down alleys that weren’t a high priority for the government organization running the repairs. Not everything is a postcard, he wanted us to know.

There are some incredible buildings that are just shells now, their interiors completely deteriorated, trees growing where there had been bedrooms and dining rooms, birthday parties and lovers’ trysts. For many of them, scaffolding is in place not for any on-going restoration but just to support the crumbling exteriors.

But there is some hope that tourist dollars will support continued restoration. And for some of those grand buildings, they might get their second lives as hotels and host birthday parties and romantic rendezvouses once again.

2. Riding in a Classic Car

Our group gathered for dinner in our hotel lobby when our tour director told us the bad news.

“Our bus broke down. The driver can’t get it started.”

I was already ravenously hungry, so I started to think about what I could start gnawing on to stave off hangriness.

And then came a cacophony of horns and sirens, as a classic car gang (seriously, that’s how I would describe them) came roaring up the drive.

“So I called in some replacements!” our tour director yelled over our squeals and laughter.

We clambered into the cars and took more pictures than were strictly necessary, then pulled out of the hotel’s driveway, egging our driver to race the other cars.

3. The Buena Vista Social Club

The original Buena Vista Social Club is sadly no more, but a sort of tribute performance lives on. Is this kitschy nostalgia just for tourists? Perhaps. Do I love that kind of stuff? YES. The Buena Vista Social Club calls back the hedonistic days of rampant tourism in Cuba, prior to the embargo and travel restrictions. The performers prove again that Latin dancing is the most sensual of all and you will also leave with Guantanamera stuck in your head.

4. The Community Band in Caibarién Square

Perhaps the only thing better than imaging I was partying at the original Buena Vista Social Club was actually seeing an original member of the band. Wandering through the small town of Caibarién one Sunday afternoon, we stumbled upon the only life in the town – the community band performing in the town square. We lingered, taking pictures, enjoying the music, even dancing, when our tour director pointed to an elderly man sitting next to the trumpet section, the sunglasses over his eyes not masking his delight and emotion in the music.

“That’s one of the original trumpet players of the Buena Vista Club,” she said. “He usually conducts the band.”

But he was getting older, and now he was enjoying the music just like the rest of us.

5. Cuban Cowboys

Outside of Havana, Cuba is rural. There were few cars driving the highway between towns, and horse-drawn carts were commonplace.

As were the cowboys.

Talk about romancing the past.

6. Learning about the Essentials of Cuban Life

Namely, rum, coffee, and cigars. Was this demonstration all kitsch for tourists? Maybe. But there’s something that caused giddy excitement in our whole group as we were served sugar cane juice with a splash of rum at ten in the morning.

We were instructed on the proper way to light and smoke a Cuban cigar and then got a peek at a matronly Cuban woman rolling cigars (in the shop, of course). Cigars aren’t really my thing, in the end, but man did I feel like a badass Bond villain that day.

7. Turning 30 in my 30^th Country

When we booked the trip and I realized this overlap would happen, I turned to my then-roommate and said, “I’m going to turn 30 in Cuba! How many other people can say that?”

And she said, sensibly, “Well, most Cubans.”

But seriously, what a special experience to have my birthday on this trip. The bus driver presented me with a rose as I boarded the bus that morning and everyone sang me happy birthday. Our tour director made sure I was completely pampered. We stopped to hear a Latin Grammy-nominated musician as part of our people-to-people program and he sang me Happy Birthday. There was a rum-doused flaming cake at dinner that night. And, since we were staying at an all-inclusive resort on Cayo Santa Maria, there was as much champagne as I wanted.

8. Dining at Los 500 Años

Private restaurants, or paladares, are still a relatively new thing in Cuba. When they were first legalized in the late 1990s, entrepreneurs could only open them in their home, hire people from their household, and have less than twelve seats. Since 2010, the regulations have loosened significantly, allowing us to dine in some truly wonderful restaurants.

My favorite was Los 500 Años, one of only two paladares in the town of Sancti Spiritus. It kept the home-style spirit of paladares alive – tables were crowded into the rooms and halls of a private home and I peeked behind the shower curtain in the bathroom to see the chef’s shampoo brand.

I’m a creeper, we all knew that.

9. Seeing Hemingway’s Cuban Home

Hemingway isn’t my favorite author, but you’ve got to admit the man’s got a certain blowhard charisma. So visiting his house was more of a case of intrigue than admiration.

One of the things I loved about the house was that we weren’t allowed to go inside. Visitors can only peek in through windows and doors. It lets you fill the space with your own cast of characters. You can imagine Hemingway reading a newspaper and drinking a mojito in his living room. You can see visitors admiring his hunting trophies in his study. You can hear the laughter of a dinner party at his dining room table.

It definitely made the alcoholic tortured writer’s life seem very appealing.

10. Cayo Santa Maria

While all-inclusive resorts aren’t normally my accommodation of choice, on Cayo Santa Maria I did have my first glimpse of a Caribbean beach.

Let’s just say – I get it now, all you Caribbean beach lovers. You must forgive me – I grew up with the Jersey shore. I had no idea beaches like that even existed outside of Photo shopped pictures on Pinterest. I’m not going to turn into a beach bum anytime soon, but I see more Caribbean in my future.

Are you headed to Cuba anytime soon? What would you most look forward to? 

If you’re interested in the tour I went on, you can check at more at Go Ahead’s Cultural Cuba page. This is not a sponsored post. I’ve been on several Go Ahead tours and have been very satisfied with all of them. Feel free to ask me any questions about their Cuba tour or operations in general.

Want to SEE some of my top ten experiences in Cuba? Check out this video, a collection of my Cuba Snapchats, and make sure you follow me at ‘wayfarersbook’ for my current adventures on the road!