How To Spend 8 Days In Cuba

Most times we are limited to how much time we take of from work and general responsibilities to go traveling.  Especially with a little one at home, I wanted to plan enough time to really experience the Cuban culture but didn’t want to spend too much time away from her.  That being said, you also want to give yourself some time to relax and recharge, and not feel like you are coming back stressed from the trip’s itinerary.

After travel time, my trip ended up being about 8 days in Cuba.  I tried to get a little bit of everything, but of course you won’t be able to get everything in such a limited time.  My cousin and I kept to a certain region of the country to not spend additional time in traveling, but I would love to return one day and learn about the rest.  I am really happy with what I ended up experiencing, and it was a perfect amount of time for me, I thought I would share my itinerary.


Arrive in Havana in the morning.  In the last post I mentioned how disorienting it was to try to find transportation from Havana to Trinidad, so we ended up spending more time than we expected there at the airport.  After arranging a ride with our driver, Jose, we were off.  We had broken conversations with the language barrier, but he was sure to point out the different fields of crops that we passed along the way: yucca, banana, sugar cane, and more.  Along the way, my cousin and I had fallen asleep and ended up waking up in the town Cienfuegos.  It was a little alarming, but we misunderstood the conversation a bit as Jose wanted to show us some things in the town.  It was really sweet of him, and I’m glad we got to see the town, but we were both kinda caught off guard with that side trip.  From Cienfuegos to Trinidad we traveled along the southern coast where we had roads full of crabs trying to cross the road.  It was actually hilarious to see crabs running across the road, and Jose even stopped the car to pick one up for me since I was so amused.  We ended up in Trinidad and met with our host family in the evening.  Ana, brought us some Cuban coffee up to our room as we started to set up our space, then we were off to explore the town.  After some wandering, we ended up at Giroud J&J for a lobster dinner and some cocktails. We called it a night after that and walked back to our casa for a good night of rest.

Jose, our driver for the long trip from Havana’s airport to our home in Trinidad.

The town hall building in Parque José Marti, the central square, Cienfuegos.

Little crab crossing signs needed.

Grilled lobster at the Giroud J&J


We woke up to breakfast on the rooftop patio by Ana.  Generally, the breakfasts there are the same around Cuba: coffee, ham, cheese, and breads.  We sat out and enjoyed the downtime to talk about plans for the day and look at our list of things to do.  We decided to explore Trinidad for half the day, walking the colorful streets and visiting major areas like Plaza Mayor to see the sights.  Trinidad is an old Spanish colonial town, with a history of slave trade, so there’s plenty of museums to see in the area.  The city is not very big, but the cobblestone streets make for some tired legs at the end of the day, so remember your comfortable shoes here.  After half a day of walking, we took a pedicab to the beach, Playa Ancon.  Known as the prettiest beach on the south coast of Cuba, it was actually surprisingly quiet.  The waters were warm and the beach was clean, so it made for a great place to hang out until sunset.  The beach is only about 8 miles from the city center, so pedicabs and regular cabs are ready at every corner to take you between the two.  After the beach, we got cleaned up at our casa and went back out for dinner.  Restaurante Sabor a mi Trinidad was such a fun experience because of the sweet staff, strong cocktails, and delicious food.  We were there for a couple hours, in their outdoor space just enjoying the night.

Breakfast on the rooftop patio at Ana’s casa.

Streets of Trinidad

Playa Ancon

Octopus at the Restauraunt Sabor a Mi

Finding the late night churro guy in the streets, he even wears a chef hat so you know it’s a serious churro.


In our Trinidad explorations the day before, we came across a guide in the streets who was selling tours to the close-by Parque Natural Topes de Collantes, one of the country’s nature park reserves.  This was something we had planned to do anyway, so we were glad to find him and get more information.  We woke up and walked to the meeting spot by the city center where we met up with him and our guide.  We were given our own guide for a day of exploring the park and it’s waterfalls and swimming holes via horseback.  Usually, I am a little weary about travel experiences on horses but in the end, this was a great way to see the park.  We stopped at a sugar cane plantation on the way in where we were able to have fresh pressed sugar cane juice and rum, then we were off to find the waterfalls.  Because we went during the dry season, a lot of the waterfalls weren’t running, but we got to see a little trickle.  The caves and lagoons were so relaxing, and we felt like little kids swimming around in them.  We spent the best hours of sunlight swimming around, and as an added bonus some of the locals set up a little bar close by and were serving strong mojitos as we soaked in the waters.  The experience was kinda priceless, but came at a surprising cost.  Aside for the cocktails along the way, the whole package (horse, guide, and food) was about $15 making it one of the less expensive all-day excursions I’ve even been on.  When it was time to ride back in, we got to stop into the small settlement in the park, where the locals have set up a small outdoor eatery with bar and live music. Other groups on the tours were there as well and we all enjoyed the views as the horses grazed in the open fields.  We got back to Trinidad a a little drained from a full day of activities already, but ended up cleaning up and still going out.  We met some a couple really sweet guys from Greece at Hotel Iberostar, let me tell you how great it was to finally be able to speak English from a couple days of my struggling Spanish. We had a great time drinking and talking with them, spending the night dancing at one of the many salsa clubs, bar hopping to find the perfect Canchanchara (the specialty cocktail of Trinidad), and eating some late night Cuban sandwiches to soak up that alcohol.

You know you wanna swim here.

My horse, Colona, taking a break so we both can eat.

Jose and the sweet table-side serenades. A night out for a couple cocktails and some music.

Late night sandwiches help to soak up the rum.


Waking up to another breakfast by our hostess Ana, we were already mostly packed up.  Ana had arranged a driver for us and a couple of girls from Argentina to Havana.  The 5 hour trip was mostly spent sleeping off the night before and all 4 of us got some needed rest.  We arrived to our host family’s place in the Vedado neighborhood in Havana in the afternoon.  Our hosts Juan and Marta had prepared a map of all the locations we may need; like cash exchanges, restaurants, and wi-fi locations.  We talked with them about our plans and what they would recommend and they were so helpful.  After unpacking a bit, Juan walked us over to the John Lennon Park close by the house to show us the infamous statue, then walked us over to the restaurant that he recommended.  He was sweet enough to even tell the host to take good care of us.  We had an amazing meal at La Cathedral and walked over to the Cohiba Hotel close by to get some wi-fi to plan our stay in Havana.  We ended the night walking around Vedado; exploring the streets, getting familiar with our neighborhood, and even catching the sunset on the beautiful Malecon. The night ended early to get some rest for the second half of our vacation in Havana.

Our driver’s dash, it was a picture in his cell holster which didn’t fit his cell phone, but he still kept it up for the view.

Our host dad Juan walking us to the park.

I didn’t have a good food pic at La Cathedral because it was so delicious, we ate it too fast.

Sunset and people watching on the Malecon.

Ending the night with dinner, drinks, and some music at Union Francesca.


Exploring Havana.  We walked around meeting new people at various parks and hotels.  We skimmed by areas off the Prado Paseo like  Old Havana, and Revolution Museum, and other popular destinations of Havana.  We definitely got schooled in ways of getting internet that day, as I was trying my hardest to get some decent signal to have a decent conversation with everyone back home, especially my daughter.  We had lunch at the restaurant in the Havana Libre Hotel and shopped the nearby open air market for some wi-fi cards. Daytime exploring became nighttime adventures, as we stepped on for some dancing on a Friday night in Havana.  We went out to the club Sarao in Verdado with a friend we had met, Daniel, and met some friendly State-side people from Jersey to hang with.

Really beautiful classic cars are everywhere.

Havana on foot.

Havana Libre hotel.

Lovely conversations and chance meetings of Ernesto at the local wi-fi park.

Adventuring into the Friday night life of Havana.


Woke up early to board a bus for Viñales.  Another colorful colonial town in western Cuba, it had a similar look to Trinidad.  I started the day off with “the hair of the dog that bit me” and found myself at Guayabita Rum Factory.  Pinar del Rio is the western province of Cuba, and it is where you can find these tiny little guava fruits used to make a very special rum.  A quick tour and a tasting, and I was in love.  Seriously, I love guavas so this rum was magical for me. Its not too sweet, but you can’t mistake the subtle hint of flavor when you try it.  I looked for another bottle of that around Havana with no luck, but someone mentioned you can pick it up at the Duty Free in the airport in case you don’t make it to the factory.  From there, I headed into nature. Parque de Viñales is a National Park known for it’s mogotes, large hills and mountains that seem to just pop up from the flat ground.  Close by are the Indian Caves with it’s  underground rivers that I got to explore around with a group.  A boat took me from the interior walking paths through the underground river where you pop out just in time for food.  The tour included a big lunchtime meal, complete with another guitarist to play such favorites as “Guantanamera” as you eat.  Trust me, you will hear that song played almost every place, everyday, for your entire time in Cuba, you will know the lyrics by the time you leave. After lunch, the bus made a quick stop at the Mural de la Prehistory, a large painted mural in the National Park, depicting evolution (although it features snails, dinosaurs, and people… so I’m not sure that I follow the evolution there).  It was impressive and confusing all at the same time, so I was glad the bus only stopped for a short time.  Viñales is also known for the rich clay ground, which makes the perfect location and conditions for tobacco growing.  The best tobacco in the world is grown and exported from this region, so it was only right to visit a tobacco farm.  These tobacco farms provide the government 90% of their crops to get packaged, sold, and exported for all of the well-known cigar and cigarette companies. 10% of the best crop is left to the farmers discretion, kept in the family and sold on the farms.  I got a lesson on the art of hand rolling cigars and got to smoke one at the source.  My day in Viñales was ended at the hotel, Horizontes Los Jazmines, with it’s unbeatable views of the valley.  This excursion was about $65 for everything, but it included so many activities with food and long transit times so I feel like it was totally worth it.  After that, I got back on a bus for the almost 3 hour trip back to Havana.

Cutie little guavas for making a very special rum.

Under the mogotes with caves and rivers.

Yep, still snails, dinosaurs, and people….

Cuban cigars are hand-rolled and come straight from the source.

The amazing view before loading the bus back to Havana.


Breakfasts with my host family was always a pleasure, I practiced my Spanish with the sweet Marta, as she put out a beautiful spread of fruits, home-baked cake, ham and cheese, and of course the Cuban coffee.  I spend the day going to Habana Vieja, Old Havana.  Museums/monuments, street wandering, people watching, and eating great food basically took up a whole day, but I was also escaping the on and off rain that day.  I spent some time going back to the casa to do some work and ended up showing off family pictures and stories with Marta for most of the day.  Close by, the Plaza de la Revolución and The Colon Cemetery were great places for quick sightseeing between the storms.  The weather there could change with the quickness, so be sure to come prepared.  I ended the day back at La Cathedral for dinner and was not disappointed again, seriously I loved everything I ate there and am dreaming about that bombom coffee drink now.

A crumbling Havana.

Getting caught in the rain.

Getting some time to edit photos and have tea with my host mom, Marta.

Colon cemetery, named for Christopher Columbus.

La Cathedral’s bombom, a coffee drink with condensed milk.


Our last day in Cuba together, Kathy and I were both excited to have the sun back out and were ready for some relaxing time to really just enjoy the city.  We walked Vedado to the Plaza de la Revolución for some better (drier) photos, and then hopped in a “cocotaxi” to closer to the Paseo Prado in the center of Havana.  We spent some time in the beautiful Hotel Seville for some internet connection and then walked to Havana 61 to make dinner reservations for that night.  We wandered Habana Vieja for a while as I wanted to take some photos of the amazing city, somehow the vibrant colors and people at juxtaposed next to these old and crumbling buildings, making it something of a curiosity.  We visited La Floridita, one of the many Hemingway bars, and tried the most delicious daiquiri I’ve ever had.  We visited the Romeo and Juliet Cigar Factory where the shop has carries all sorts of famous Cuban cigar brands (and rum too if you are looking to bring back more alcohol).  We stopped at the famous “socialist ice cream parlor” in Coppelia Park to try some of the many flavors.  We were both pretty disappointed to see there were no crazy lines or a plethora of flavors, but strawberry and a chocolate-vanilla were the only flavors available.  No specialty sundaes with sponge cake sides or various toppings, just syrup or cookie crumb “sprinkles”.  It was still a nice treat to a warm day and we got to smoke some of our cigars as we ate our ice cream, but definitely not what I was expecting for how nice that place looked.  We had some time to fully walk the Malecon, roughly about 5 miles, at dusk.  What a beautiful walk to enjoy the views of the fishing boats off the coast on one side and the bustling Havana lights on the other.  The waves get pretty high and can knock a passing bicyclist down on the road, so we walked on the city side until we reached Old Havana again.  We met up with our Greek friends from Trinidad, who were back from their travels around Cuba, for dinner at Havana 61.  We all got to enjoy the good food, good drinks, and good company again, and it was a great way to end our trip.

Our cocotaxi, basically a scooter with a fiberglass shell.

Walking Habana Vieja.

Daiquiris and Hemingway.

Shopping for cigars at Romeo y Julieta.

Ice cream break at Copellia.

Ending our time in Havana with the same two who shared our last night in Trinidad.


Ready to leave for the airport and head back home.

In writing this list, I do feel like we had a lot of relaxing time with some really fun activities in between.  I try to remember to plan a couple things per day for a trip and try to keep some room for general adventuring, but I felt like most of Cuba was a little bit of finding activities on the fly.  It didn’t matter though, I think we made some awesome arrangements by just exploring around.  There were areas that a local would tell us not to venture down, or where a cab driver would walk us into a building.  There were instances where our hosts had the perfect recommendation or arranged our driver for a trip.  I feel I’ve met some really great Cuban people who are so helpful and invested in showing us as travelers a great time while we are there.

In 8 days we visited 4 cities, a couple Unesco World Heritage sites, did some city life, some nightlife, some nature, and still had some downtime to relax.  Although at times I felt homesick for my creature comforts of home, there’s something freeing about being a little isolated from the world.  The initial disconnect can be a little disorientating, but from that you can really start to experience everything that this country has to offer and be engulfed in it’s beauty.  There is a lot Cuba has to see and I can’t wait to come back with Evie one day to show her.

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