A Life in Travel

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Americans Traveling To Cuba: What To See and Do


Americans visiting Cuba are required to to be part of an exchange with 5-6 hours every day spent engaging with Cubans in an "organized fashion," in our case a people to people tour. We couldn't just go to chill or play, it had to be structured. We went with Wildland Adventures, owned by my cousin Kurt Kutay and his wife Anne, and 13 other adventurous travelers, who accepted us as travel family. It was Wildland Adventure's inaugural Cuba outing, and with Fidel's death, the country was launched into an unprecedented 9 days of mourning. 

We were able to go to the Plaza de la Revolution where Fidel was being remembered. It was incredibly moving and will be one of the most memorable nights of my life. Crowds had been gathering there for 2 days to pay their respects to Fidel. There was a rally starting at 7pm for the public. We arrived around 5:45pm and expected to leave by 6:30pm but the crowds were as far as the eye could see. We tried to cross the plaza to get to our bus but we got stopped by a barrier, and found ourselves right in the middle of 400,000 people! People were peacefully chanting, singing and crying (especially the oldest in the crowd). It was a beautiful and moving experience, albeit a little scary as we got stuck at points and could hardly breathe. We were not sure we'd be able to exit before Raul Castro came out but our amazing guides were incredibly calm and didn't lose one of us.

I know there are many strong opinions about Fidel Castro and the Cuban Revolution and as far as dictators go, I'm not fond of any of them!  As we know, Fidel ousted a truly brutal dictator, Fulgencio Batista, who was in bed with the mob and killed dissenters daily. I clearly was not personally impacted by the revolution, but I grew up extremely anti-communist, so I had many preconceived notions about history and life in Cuba. Being there and seeing the country, I was far more impressed than I expected. There's plenty that needs improvement as well, such as bad planning (sugar is basically the only export) and massive dissrepair due to the USA embargo. The 200,000 people who left in the early 60s lost it all. The ones with wealth who stayed could keep 2 homes but lost their businesses. The country has suffered but they have managed to survive with warmth and hope. Given all that, I was shocked at the volume of people who showed up, of their own free will to show their respects to Fidel Castro. Our conversations here have shown a country grateful towards a man that provided education and health as foundational rights to all. Women are paid the same as men and given the same rights for advancement as well. It is still a government controlled country though. The move here is now toward quasi-socialism, and the future is hopeful with Raul Castro opening doors to change. It is amazing place because the Cuban people are so warm and the culture is so full of life. With Fidel gone, I hope more political thawing occurs and these wonderful people can spread their wings with their private ventures.

Our timing was a mixed blessing with Fidel's passing, as we were able to experience things that are once in a lifetime, but we were also there at a time of mourning, where there was no music and no dancing or public drinking for 9 days. So we did not experience the 'real' Havana but we still managed to enjoy delicious meals at many private restaurants (vs state run), called paladars, where they served wine, beer and cocktails, and fantastic service. Food is naturally organic as the embargo has left them without pesticides (one good outcome!) Ropa Vieja was one of my favorite dishes so I got it a few times, but we also had great seafood and exceptionally delicious pork, and oh so yummy flan! Despite the time of mourning, we learned a ton and realized we need a trip back to Havana for a long weekend of music once the doors are fully opened for Americans. 

The architecture of Cuba was stunning but also gave pause to contemplate how people live in what appeared to be some uninhabitable dwellings. From Paladars (privately owned restaurants), to Casa Particulares (privately owned bed and breakfasts) to churches and old homes along cobblestone streets, we saw great variety. We saw the spectrum with some dilapidated homes next to beautiful spots.

We visited a medical clinic in Santiago de Cuba called a policlinic, where Cubans go for specialists and semi-urgent care. Each Cuban has a 'family doctor team' that serves a neighborhood, and each person is requested to see this Dr. at least once per year (there is a big focus on preventative medicine). These teams have office hours from 9 - Noon, then spend the afternoon making house calls and tracking down patients. We met with a team of doctors and nurses, mostly women, who represent 53% of the 73K Drs in Cuba! They were well spoken, open to all our questions, and very proud of their work. No medical fees are charged except about $2 for eye glass frames. Their skill capabilities seemed strong but the facilities can't wait for the embargo to be lifted to get much needed medicine and equipment.


  • ​Dress Casual - The sun is intense, so plan accordingly with a hat and sunscreen. I would recommend comfy sandals. For dinner, if you choose one of the nicer spots, wearing a skirt or capris is typical.
  • Money - The American government won't allow for credit cards to be used in Cuba, so you'll need to get cash immediately. The currency is CUC (pronounced kook). It's basically a $1 CUC to $1 USD, less 20% exchange fee. Don't get the Cuban peso - long story, there are 2 currencies, but CUC is the one you want.
  • Phone - Verizon and AT&T both work but are expensive. You can keep your US phone on just for texting - 5 cents in and 50 cents out.
  • Wifi - You can purchase a card at local hotels, and use the card at local squares but my advice would be to wait to get onto your ship to connect. It's not worth the hassle.


  • ​Overall the shops carry most of the same things. Literally. But there are unique shops, especially for art, so walk Old Havana and pop into places. The Clandestina map has shops that are privately run, check those out for sure.
  • Clandestina - is a store in Old Havana and is a must go to for the "Actually, I'm in Havana" shirt. Get the Clandestina map at their store. If you get this early on, it'll help you decide where to visit.
  • Fusterlandia: Havana has some amazing artists. The art scene has been flourishing and there are many galleries. With limited time, I suggest you make a point to get a taxi to take you to Fusterlandia. It's an entire neighborhood that one artist has transformed. It's amazing and totally worth the visit.

  • ​Enjoy the squares - Stop and have beers (our favorite was Crystal).
  • Have Cuban coffee which is made with sugar that is whipped with a little espresso and added to the espresso cup.
  • The Malecon is the sea wall where your ship docks and is a major spot for locals and tourists to enjoy hanging out along the sea.
  • The Five Plazas - You MUST check off all 5 of these, as it gets you to walk all of Old Havana and you'll see a wonderful mix of architecture.  
  • Calle Obispo - This street has lots of shops, galleries, old hotels, cafes and one of the plazas.
  • Paseo del Prado - You'll no doubt walk this street. It is very well known and Chanel recently used it for a fashion shoot. 
  • The Capitol and the Opera House buildings are located across the street from each other and across from Central Park, the best spot to get a taxi tour. The capitol building is designed after our own US Capitol.
  • The National Ballet/Opera House building is stunning. It was refurbished for Obama's visit in 2014 and showcases gorgeous architecture.
  • El Morro Fort - On your taxi ride, ask them to take you to the fort across the channel from the cruise ship. It dates back to 1775. It is a beautiful spot with great views across the channel to Havana.
  • Stop and enjoy music - It'll be everywhere. Bring some energy drinks so you can stay up and enjoy the night!


  • El Dandy - #5 on TripAdvisor - They have great tacos and it's located near El Clandestina. It is very casual, very local and a great spot to eat lunch and people watch.
  • Starbien: # 6 on TripAdvisor - It is located in an old house and the food and atmosphere are amazing.
  • Los Naranjos: #52 on TripAdvisor - It is located in a beautiful old home with a stunning garden setting. It is very classy, has wonderful food and is an excellent spot for dinner.


  • ​Hotel Saratoga has a rooftop pool bar, great views of Havana and a great lobby bar.
  • Sloppy Joes - you just have to.
  • Nacional Hotel - Historic location and great drinks!
  • Hotel Ambos Mundos has a beautiful lobby. Grab a drink and try to channel Ernest Hemingway. You can pay 2 CUCs to see the room he lived in until he bought a home in Havana. 

Our trip was back-to-back learning experiences and we barely skimmed the surface of this complex country. Cuba is a country of proud, happy people, diversification, fantastic architecture, constant change and much disrepair. It's full of surprises! We learned so much, laughed so much and fell in love with Cuba.

Viva Cuba!

Wildland Alumni, Lucy Gillard

To learn more about trips to Cuba with Wildland Adventures Click here


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