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What Traveling to Cuba is Really Like

Havana, here I come! I’m traveling to Cuba, and as I sit here at my boarding gate, I’m equally excited and nervous for the experience ahead. This will be the first time I’ve been to Cuba, as it was previously prohibited for U.S. travelers to visit, and while ‘backdoor’ methods existed, I had never taken the opportunity. I’m excited because Cuba will be an adventure — a new place, a new adventure, and new people to learn from! I’m nervous because… well, sometimes you just don’t know what to expect! Especially in a place that doesn’t have any ATMs you can withdraw cash from and where they don’t take U.S. credit cards anywhere in the country. So off I go to Cuba, a wad of cash in my pocket, prepared for the adventure of a lifetime!


 In all my research and conversations with people who have recently been to Cuba, I’ve compiled a list of the 10 most important things to check off in a journey to Cuba:

  1. Stay in casas particulares, or local homestays. Cuba heavily regulates the tourist industry, but these casas particulares enable travelers to stay and visit with local Cuban families who open their homes and hearts to travelers. Many of these homes date back to the mid-19th century and are absolutely beautiful

  2. (For U.S. travelers) Bring euros or Canadian dollars. The exchange rate from euro or Canadian dollar is much better than what you get from exchanging U.S. dollars for CUCs (the special currency designated for tourists)

  3. While Cuba has internet, it is only available in specific locations… plus it costs a lot of money so you should always sign on, download all your emails, and then sign off to save a few dollars ($12 U.S. dollars buys you two hours of internet in some places).

  4. Declare your purpose of travel as “support of the Cuban people.” The U.S. has specific guidelines on why visitors can enter Cuba, and “support of the Cuban people” trips are definitely still allowed. (Acanela Expeditions runs all of its trips with this purpose in mind, which is why Acanela’s still taking people to Cuba!)

  5. Bring your favorite snacks with you (and plenty of extra condiments). This one may sound funny, but Cuba still has trade restrictions of what can be imported into the country, which means you won’t find many comfort snacks from home at the few convenience stores scattered around the cities.

  6. Do not bring a large suitcase — Havana airport is notorious for losing baggage, so pack light and bring a carry-on.

  7. Look for a knowledgeable local guide to lead your experience. Not only will you have a better time with someone who knows the ins and outs of the country, you’ll also be able to hear a rich side of history from a local.

  8. The must-see locations include Havana, Viñales, and Trinidad. If you’re feeling adventurous, I would add Santiago de Cuba and Baracoa (on the east of the island)… but it is a journey to get there by land!

  9. Visit the local restaurants, and be prepared to witness traditional music and salsa dancing — Cuban food is pretty great, and the culture is lively and exciting!

  10. Make sure to get your visa in advance. You can use a service like VisaHQ to get the help you need. Some airlines offer assistance, and some actually issue at departure. [That said, you should double-check the airline policies frequently as they can change]

Once I arrive, I think I’m going to keep a travel log of all of my Cuba adventures… that way, I can really remember what traveling to Cuba is like.



 I’ve landed. Here we go.

Traveling to Cuba is like stepping back in time: classic cars, crumbling buildings, no grocery stores, sparse internet, and home stays instead of hotels. In just a few hours, I feel like I now understand why people come to this beautiful country — as it gives you the opportunity to time travel. 

I arrived at 4:50 into the Havana Airport, a dirty and very dusty building with several beat-up airstrips. I was lucky enough to be met by an enthusiastic Alber, our guide for our Havana to Santiago journey. He recognized me the moment I exited the airport and we were off just like that — with his two drivers as company, of course. In Havana, we visited the neighborhoods of Centro, Vedado, Miramar, and Habana Vieja, and we stepped into numerous beautiful accommodations along the way.

 I am staying in B&B Havana Central. After a tiring day walking through many different districts of Havana, I was met back at my casa particular by Roxanne (the owner) and Japones (the manager). While Roxanne entertained her guests, Japones continued to stop by my place in the sitting room — passing me two bananas, then a bottle of water, and lastly a delicious chunk of pineapple that was left over from dinner. Since I was exhausted and famished, his small gesture meant a lot. Cuban people are very kind.

 The only complaint I have with Cuba is the lack of Internet access, which really makes communicating back home very difficult.

Not having internet makes you realize just how hard it is to be unplugged. I spent 9 CUCs ($12) on two hours of internet this morning so I could speak with Andrew about what occurred in the 24 hours since I departed the USA. Only 24 hours without internet? I’m not sure if I have gone that long without it in years, which I’m very embarrassed to admit. I was up late this evening, as two of our travelers lost some of their luggage (welcome to Cuba, everyone)…  at least everyone got here safe and sound, and everyone is excited to start our tour tomorrow! A tip I’ve learned in talking to experienced Cuba travelers: don’t check your luggage!



 We awoke to the sounds of birds in our beautiful casa particular — and the smell of a delicious breakfast being prepared. Alber arrived at 9 a.m. and presented us with beautiful hand-crafted gifts. Receiving a little gift upon arrival is always an exciting touch to the start of a trip. We packed up all our luggage, and headed out front of our casa for Alber’s second surprise: two old American cars to pick us up outside our casa.  Havana is known for its colorful buildings and beautiful old cars, and this morning sure wasn’t a disappointment.

 We continued out afternoon with a visit to the famous Hamal street (which is only open on Sundays) and a street that perfectly showcases Cuban-Afro art, music, and dance. Right next door was the famous pizzeria “A Mi Manera,” where the hand-crafted pizza is lowered via a rope from three stories above (where the kitchen is located) to the guests ordering from the sidewalk/street area. We also spent some time picking up the luggage at Havana Airport before departing to Trinidad (we are currently en route). We did have the opportunity to stop at the famous local ice cream place where Cubans wait in line for hours to eat the best local ice cream in Havana — luckily we bypassed the line as we were escorted to the “tourist” ice cream stand. Not as good, but definitely not as long of a wait.

 Tonight we will arrive in Trinidad a little later than expected but with all our luggage.  Talk with you then!



 So we arrived in Trinidad, but not with all of our bags. We had one bag arrive (five hours later than expected) and one bag lost, which means it was probably stolen in customs. Due to the baggage delay, we arrived very late and did not get to stop at the cenotes or see the beautiful Trinidad mountains, so luckily we are coming back this same way. We are staying in two beautiful colonial mansions, Casa Mauri and Casa Colonial 1830. Both have vaulted ceilings, beautiful tiled walls, and crystal chandeliers, not to mention the beautiful birds in the central courtyards that we’ll wake up to in the morning.  Despite the lack of many basic amenities, this place really is a dream.

 Our day in Trinidad was beautiful.  We visited the main plaza in the morning to see the locals in action and to walk the beautiful cobblestone streets.  The colors of this city are amazing — bright blue, red, yellow, orange, and green buildings line the streets, with old Pontiffs, Fords, and Chevrolets in every color imaginable.  The people here are so friendly, and you constantly hear music playing in the streets — and Cuban Music is very good!

I have made some very good friends, including two new adopted grandpas who tried to give me their cigars, which I almost couldn’t decline because they were so cute! In the afternoon, we continued on for a horse ride through the Viñales Valley, where we even encountered our first Cuban rainstorm. Riding through the jungles was stunning, and we had the chance to hike at the end of our tour to a beautiful waterfall.

Our evening was once again filled with a delicious dinner and a cultural Afro-Cuban dance show, definitely a unique twist to the end of the night.


Today was incredible. We woke up early to depart from Trinidad to Santiago de Cuba, all the way on the East Coast. En route, we stopped in many beautiful places, such as the beautiful sugar mill valley overlook, where we could see the entire sugar mill valley spread our below us. We visited the tallest tower in Cuba and were serenaded by one of the best local bands in Cuba, and I even learned how to play one of their instruments. Our journey was long, departing Trinidad at 10 a.m. and arriving at Santiago de Cuba at 9 p.m. — that being said, it was well worth it. 


Roy’s Inn is the top-ranked casa particular in all of Santiago De Cuba, and sure enough that is where we stayed. The breakfast was delicious, and the casa is only a few blocks from the main plaza (where you can find the Wi-Fi). We spent the entire day visiting beautiful sites like the oldest house in Cuba, the Cuban Museum of History, and the Cathedral in the square, and we even took the time to visit the best restaurant in Santiago for lunch and climb to the top of a Moorish castle before setting off to home for dinner. Tomorrow we visit Guantanamo Bay and Baracoa before continuing on to Moron, and we are very excited! 


The time is 2:30 a.m., and I still cannot go to sleep. We arrived at our casa at 1 a.m., much later than we ever anticipated. We have learned that Cuba runs on two different time zones: regular time and Cuban time.  Cuban time means that when you ask a local how far you are from your destination, you take their answer and multiply it by five — it’s all part of the experience. 

Today was beautiful. We stopped by Guantanamo Bay (where GITMO is located) and learned about the USA territory that is leased from Cuba for $4,000 per year to house our most highly protected prisoners. We continued on to Baracoa, where we learned about the recent hurricane, chocolate production, Christopher Colombus, and even took a boat ride through El Yunque Canyon and Humboldt National Park. Alber made sure that we stopped at the best restaurant available for lunch, which was absolutely delicious! 

We did not leave Baracoa until 4 p.m., which meant that we arrived in Moron (back on the west side of Cuba) after midnight. It was a long day, but we are all excited for snorkeling and scuba diving tomorrow.



Scuba diving was incredible! We woke up early to depart for the garden of the Kings in Cayo Coco, one of the most biodiverse regions in Cuba. Our stay in Casa Alicia was beautiful, and the accommodations are very close to the city center of Moron with some of the best bathrooms in all of Cuba. The owners of the casa, Yuli and her husband, are some of the most kind people that I know. They served us a delicious breakfast, and then we were off to Cayo Coco for our diving experience with Marlin Dive. 

We arrived at the dive center around 10 a.m., ready for our dive experience. For those certified divers, they went out to do their first deep-water dive, while the beginner divers (those who never dived before) did a training course in the pool before going out for their shallow-water dive. Cuba is a great place to learn how to dive if you have never done it before.

We spent the entire day out on the water (on the beach and in the water), then returned to Hostal Alicia in the evening for a delicious dinner before spending the evening walking around Moron and sitting down in the plaza to use the incredibly fast Cuban Wi-Fi.


I believe today was our first opportunity to sleep in on our entire trip — yet no one in our group actually slept in! We were too excited to get up and start our day! After another delicious breakfast, we were off to Santa Clara, the home of Ernesto “Che” Guevara, one of Cuba’s three revolutionaries.

When we arrived to Santa Clara, we checked into our casa - one of the most beautiful restored Cuban mansions in all of Cuba. It has five rooms, three huge salas, and a beautiful inner courtyard, with every room filled with antiques from the Cuban colonial period. Hostal Cordero is by far one of the most beautiful colonial mansions we’ve stayed at during our time in Cuba.

After we checked into our lovely accommodation, we continued onwards to visit the Mausoleum of Che and take a city tour of Santa Clara. Today is Saturday, so everyone is preparing for Mother’s Day tomorrow, which means that everyone is purchasing cakes and flowers for all the lovely Cuban women!



We are on our way to La Habana after circling the entire island of Cuba! En route, we will stop by the Zapata Wetlands to dive in a cenote and swim in a fish cave just outside of Playo Largo. What we did not realize about this part of the world, is that it is actually the place where millions of crabs cross from the forests to the ocean to lay their eggs, a really unique world phenomenon that can only be witnessed during certain times of the year. We saw only a few of the crabs cross the road as we drove back to Havana, so I will have to return for the next crab season!


Today, we spent a full day in Havana, stopping by Ernest Hemingway’s famous estate just outside of the city. I quickly fell in love with Ernest, as his entire house was decorated with items from his safaris in Africa. He sure was a man of charisma and creativity (and a great friend of Fidel Castro). I purchased his book “The Old Man and the Sea” and plan to read it as soon as I get home!

After Ernest’s visit, we made our way to Old Havana, where we spent the rest of the day walking down Obispo Street and many other beautiful areas… I sure love this city!


We decided to spend our last day in Viñales, the home of the Cuban Cigar. We visited an artisan cigar factory to learn how the famous cigars are produced and then set off on a horseback ride through the tobacco plantations and coffee fields. It was a beautiful experience that I will never forget.

On our way back to Havana, we stopped by several beautiful caves, and we even took a boat ride through them. We arrived back to Havana late, just in time to enjoy one last evening in our beautiful casa.


After a relaxing morning, we set off to the airport to catch our flights back home. This has been a great trip, but I cannot wait to return home to all the family and friends I left behind. See you soon, L.A.!

To experience your own trip just like Kylie’s, book our Cuba expedition! We’d love to show you around this show-stopping country.

Post written by Acanela Expeditions CEO Kylie Chenn