Our 15 day Cuba Itinerary – Video

By Marae

We knew our time on the island was not going to be enough. It was my first time back, and spending time with my family was our number one priority. It was also my hubby’s first time in Cuba. With this in mind, we knew we had to come up with a good itinerary that covered highlights, memories and family.

Havana, Guantanamo, Varadero, and Pinar del Rio.

I was dying to go diving on the jardines de la Reina reef, but adding one more stop ( and in the Cays ) to our already tight itinerary was virtually impossible. Travel in Cuba is complex at best. Nonexistent at worst. But my mom’s last flight in Cuba caught fire (she’s fine, they had an emergency landing and nobody was hurt) so taking a flight was out of the question.  The roads are dark and under kept, the cars are ancient and we were tired. So we decided to take the bus, with the exception of a few short car drives.

Day 1  Land in Havana – Get settled and explore Habana Vieja

Our Flight  came in the afternoon and even thought it all went relatively smoothly, it still took a little over an hour for us to leave the airport. My cousin was waiting for us with a car outside, but you can get a cab as soon as you walk out. It costs $20 CUC ( About $20 usd ) and there are plenty of options. Yes, they are mostly the old 50’s cars so you can ride to your hotel or airport feeling very much in Cuba.

We went walking around old Havana, watched the sunset sitting on the Malecon, and had dinner in China town. It was a perfect day to start familiarizing myself with my home again.

Day 2  Havana – Exploring the highlights 

Since it was Roger’s first time on the island, we went for a full tour of old Havana. My uncle, who passed away last year, was a UNESCO appointed architect in charged with restoring the city. There has been a tremendous amount of work done, and it truly is looking so beautiful.

We visited the national theater, the Capitol, the old fort, the museums, the Russian orthodox church and the Cathedral… we even crossed to the Christ on the other side of the city. It’s a great point from which to look at Havana. We had lunch at a local cafeteria and dinner al fresco in a local “paladar”.  We walked a total of 12kms that day.

Day 3  Bus Havana – Guantanamo

It’s hard to predict the schedules in Cuba, but when we went in October 2018, the bus was leaving the Central Havana station at noon.

The bus station is fairly organized and the whole process went by smoothly. We had lunch at a restaurant the bus stopped at in Santa Clara. I wrote a detailed post about this journey.

Day 4  Arrive in Guantanamo

We arrived in Guantanamo at 8am. My uncle picked us up and we immediately went to his house where my aunt was waiting for us with all kinds of delicious food.

This was a lazy day as we did not sleep well the night before and we were catching up with the family. We spent all day talking, eating, playing with the kids and showering under the rain…just like when I was a kid.

Day 5  Guantanamo – Visit the Rock Zoo and Eat in Downtown

Guantanamo is know for its Rock Zoo, it is a park where everything is made of carved rock. It is actually pretty impressive. I used to go there as a child with my grandparents, and now it has become a big local attraction.

No visit to Guantanamo is finished without eating the local food at one of the many restaurants in town. When you walk around downtown, you see that there are many “casas particulares” ( homestays ). The ones with the blue sign are equivalent to airbnb ( most of them are listed on the site) and the ones with a red sign are motels that you can rent for by the hour.

Day 6 Guantanamo – Visit Baracoa and Moa beach 

My parents talk about Moa beach often and I grew up hearing stories of our summers there as a child. I didn’t remember much from it, but it truly is something not to miss.

Cuba has wonderful beaches all around, and even though the beaches in Guantanamo are off limits, my uncle says they’re incredibly beautiful. Baracoa is a nice town and one worth visiting.

Day 7 Visit Santiago de Cuba and Take bus to Varadero 

We left Guantanamo early in the morning, so we could spend all day sightseeing in Santiago de Cuba. The city has been restored much like Havana, and it is home to the Carnivals.

Unfortunately they were not happening when we were there, but nonetheless it is a city not to miss if you are interested in Cuban history, culture and music. We took a night bus back to Varadero.

Day 8 Varadero

We arrived in Varadero around 10 am and the hotel immediately let us in and gave us the all inclusive bands even though our rooms were not ready. One thing to note, is that you can stay at “casas particulares” for a fraction of the price you pay at the hotels, and the quality of food, drink and service is not amazing.

We chose to stay at the hotel solely because our stay was so short, and we had already traveled for so long. It did not make sense to take a car to and from the beach as well, and the hotels are the only ones with beach front property. If you are going to stay at one of the hotels make sure you book it before you get to Cuba. We were quoted $330 CUC for two nights from the tourism office in Guantanamo, and ended up paying $126 USD for the exact same hotel through a booking site.

We watched the sunset, walked around the beaches, climbed palm trees and danced the night away.

Day 9 Varadero

Varadero is stunning. There is truly no beach like it. LOOK AT THIS WATER.

I could’ve stayed days just swimming and lounging but instead we spent some time walking around Cardenas town and the surrounding areas. We went snorkeling, paddling and even made some friends who took us dancing. It’s truly a fun town!

Day 10 Diving and back to Havana 

The bus from Varadero to Havana is only about two hours long and since it departs at 12 we thoroughly enjoyed our morning.

We went diving in the clearest water on earth ( and had camera issues 🤦‍♀️) and made it back in perfect timing for lunch before departing.

If you talk to one of the concierges in the lobby of the hotels, they can schedule for the bus to pick you up straight from reception. There are many times available and more than one company servicing this route. Alternatively you can get a cab or share a cab with someone back to Havana. The shuttle with VIAZUL is around $20 CUC per person, and I believe a cab is around $30 CUC p/p.

Day 11 Havana

Havana really is an endless destination. Every corner you turn, there is either history, culture, flavor, music or all of the above AT THE SAME TIME! It’s an intoxicating place.

From street vendors with incredibly well crafted artisan souvenirs, to delicious food being offered in every corner. Mojitos are the main drink, and even though when we went they were having a slight lime issue ( some plague devastated their citrus crops this summer) the rum is so good you can sip it all day… and we did!

We tasted different Cuban rums, from the legendary Habana Club ( 7 anejos is delicious ) to the up and coming Santiago Rum. We even did a tasting in front of the old Bacardi building which is a must see for architecture enthusiasts.

Day 12 Havana 

A day spent truly wandering around through artisan markets and shops. Whatever was left we packed into this day.

After visiting the “Bodeguita del Medio” and dancing to covers of Buena Vista Social Club on the streets, we visited the Morro Castle ( Castillo de los tres Reyes del Morro ) and I was taken back to our family’s outings many years ago. The cannon goes off every night at 9pm and they do a whole history show on what the castle was built and used for during colonial times up until modern day.

Day 13 Pinar del Rio

We hired a private car because we were so many, but you can also take a shuttle bus directly from Havana to Vinales. The reason a car is more convenient, is so that you can do a tour. Many private cars will take you for $20-$30 CUC per person, but will fill the entire car ( usually they fit 8 passengers ).

Depending on who your driver is, you usually leave early morning so you can be in Vinales at around 10- 11am. Island time is a real thing in Cuba, so schedules must be flexible. The Viewpoint of Vinales is not to be missed as it allows for a perfect picture of this amazing region. After the viewpoint we had a quick bite to eat and went straight to the Cigar making place. It was incredibly seeing how they make these cigars and getting to smoke them. They are truly delicious and a unique experience. We also visited the Cueva del Indio” with its beautiful murals made by our island’s original inhabitants.

Day 14 Pinar del Rio

We started our day going on horseback through the mountains. We wanted to truly get to know the region ( as we are planning a retreat there in 2019!!!) and so we spent all day getting to know Pinar del Rio like the locals do. We explored some caves, saw some bats, spiders and plenty of farm animals. The horses were amazing and the locals did such a good job making us feel comfortable riding them.

We ended up at a local lake and covered ourselves in healing mud before bathing in the fresh water for hours.

After lunch, we headed to the Guayabita Rum distillery, where we were introduced to this type of rum which is known for the little guavas that age inside it. Yum!!!

Day 15 Fly Back

Our last day in Cuba was a half day and was spent packing and saying goodbye. We truly can’t wait to go back, as it was such a fun experience and we feel we have so much more to discover. I cannot wait to go back and explore more of the east of the country and some of the diving spots on the cays.


Cuba is such a magical place, with the craziest mix of history and culture. It was a great trip, and even though we will change our itinerary for the next visit, I think this is a good way to spend two weeks in Cuba.

What’s on your MUST SEE list for Cuba?