Habana Rain
Cuba is much more than just experiencing those incredible Havana nights. The country is filled with lush valleys in the countryside and beautiful beaches along the coasts. Having just returned from 15 days exploring the island of Cuba, below is my self-guided itinerary that took me to most of the highlights within the country.
Habana Rain
4 Nights in Havana (or La Habana, as known by locals and Español speakers)
Most international flights will fly into Havana, so the most logical option is to spend the first few nights in the country’s largest city. Havana has endless restaurants, shopping, and landmarks that left us feeling like we had so much still to see when we departed to the next city.
During our time in the city we walked along the Malecón trying to dodge waves, explored the Castillo de los Tres Reyes del Morro,
saw the capital (which at times can be entered, but was under construction during my visit), and shopped for tourist trinkets on Obispo street.
Some of the other must-sees during your days in Havana include El Floridita Bar, where Earnest Hemingway declared the daiquiris the “best in the world” and the nearby fishing village of Casablanca which can be walked to from the castles or reached by ferry from the main city.
Mural de la PrehistoricaHoreseback-VanalesCigar-Vanales
3 Nights in Vañales
Labeled a UNESCO World Heritage Site in 1999, Vañales was my absolute favorite destination of the entire trip. I was lucky enough to be there during a week-long street carnival that comes to the small village once a year, but even on average days Viñales is a must-see.
We took a taxi out to the Mural de la Prehistorica. Created in 1959, the large, colorful mural shows the prehistoric age of the dinosaurs towering above on the side of a mountain.  The region around Viñales of Pinar del Río is also a prime destination for climbers visiting the country as the area is dotted with small climber-friendly mountains.
Most visitors to Viñales would agree, myself included, that the highlight of the region is the horse ride through the tobacco fields. With stops at a tobacco plantation and a rum and honey manufacturer we came back with a backpack full of Cuban cigars, exclusive rum, and bottles of honey as Viñales is the best place to stock up. We also took the option to have a quick trek through a cave during this excursion that had formations shaped like animals and Fidel Castro.
2 Nights in Cienfuegos
The stunning French architecture of Cienfuegos is also a must-see on the trip. The details in the buildings made me feel like I had stepped into a Cuban Versailles. Hang out on the Malecón or take a trip over to the nearby El Nichos waterfalls. If you are visiting during the winter or spring like I luckily was then visit Guanaroca Lagoon. We were rowed out on the lagoon by a local to see hundreds of flamingos in their natural habitats before they fly to Florida for the next season.
The nearby beach of Rancho Luna is the perfect stop after a morning of watching flamingos. Piña Coladas on a beautiful white sand beach? Yes please!
1 Night in Trinidad
At over 500 years old, Trinidad has become a prime destination for tourists. Take pictures in the Plaza mayor, shop the local vendors on the side streets, and eat at one of the many delicious restaurants the city has to offer.
Trinidad is also known for its nightlife. The most iconic nightlife spot in the city is the Disco Ayala, a club inside a cave not far out from the city. The walk to the cave is not in the best area, so a flashlight is a must! For a few CUC we manged to convince one of the club employees to give us a private tour during the day before the club opened – just ask nicely! If you prefer to stay in the main area of Trinidad for nightlife the primary hot spot is the Casa de la Musica which hosts a live band each night on the steps nearby the Plaza Mayor.
2 Nights in Varadero
If there is one destination to skip on this list it should be Varadero. Now if you are in search of a resort beach vacation, which I do often enjoy, then Varadero is your city. But if you want any sort of authentic Cuban experience then this is not the place to visit. Prices are significantly higher here than in the rest of the country (except on drinks – those are still 2-4CUC each!) and though the beaches are beautiful they can be found with less of a crowd in other areas of the country (such as Playa Rancho Luna in Cienfuegos that I mentioned previously).
Add this to your itinerary if you want a couple days of just relaxation – but just be aware this area is nothing like the rest of Cuba.
2 Nights back in Havana
 Leave more than just one night when returning back to Havana for your flight. We booked our casa particular in Vedado rather than where we first stayed in Centro Havana so we could have a different experience of the city. Visit the famous Hotel Nacional (though opt for drinks – not dinner there) to see the stunning building where many of the world’s most well-known people have stayed during their visits to Cuba.
We also used these days to catch up on what we missed the last time we were in the city, including Camera Obscura in the Plaza Vieja in Old Havana. After buying a ticket in the plaza outside, the lift brought us up to a tall rooftop with a small room where a guide turned off the lights and showed us, in both English and Español, the Camera Obscura. This is a live image of what is going on in the surrounding areas that is projected through a small pinhole. After you are allowed to go onto the roof and free to snap pictures from above the city – with 360 views.
Quick Cuba Tips:
  • Stay in Casa Particulars or Airbnb’s over hotels for a more authentic Cuban experience.
  • Using public transportation is not recommended in most of Cuba for tourists. The best options for going between destinations are taxis and Viazul buses which are reserved for visitors to the country.
  • Exchange money at the airport and at banks throughout your stay – but plan a few hours for each exchange as lines are long and move slow!
  • Cuba is a very safe country – but do beware of pick pocketing, especially in popular tourist areas.
Have you visited Cuba? What was your favorite destination?


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