Driving Across Cuba

Cuba is one of my favourite travel destinations. Purely because everything is so different and interesting, the streets of most towns are like walking around in a museum. Then there’s the cars, architecture, live music and seemingly old way of living that all add to the experience.

The way of life, the resilience and the hospitality of the people make Cuba unique. However, as I experienced, there is an underside of resent and desperation amongst some Cubans who are locked inside the island thanks to a revolution and regime they don’t support. Furthermore, the ever-impeding sanctions imposed by the United States puts a huge barrier between Cuba and most of the rest of the world.

Cuba Travel
‘The longest genocide in history’ Billboard protesting the US embargo

Cuba Highlights

  • Cuba’s buzzing capital La Habana
  • The historical town of Trinidad
  • La Cueva nightclub in Trinidad
  • Tobacco and farmlands in the Viñales Valley
  • The lesser visited but just as charming Santiago de Cuba
  • The best scuba diving in Cuba at Jardines de la Reina

I travelled with three friends across Cuba for three weeks which is an ideal time to get from one side of the island to the other. We arrived in Havana, rented a car, then drove across the country to Santiago de Cuba before flying back to Havana. You won’t be able to see everything in Cuba in three weeks but you can see the best parts of the island and still have time for anything unplanned (like when we crashed the car).

Cuba is slowly changing, becoming increasingly easier to travel and now has AirBnB’s, internet access and some places even accept international credit cards. The dual currency system separating locals and foreigners is now obsolete which makes things even easier. Although there is a single Cuban currency, you’ll get a much better rate on the black market than at the banks or official exchange houses.


Whether you’re arriving at the airport or the port you’ll almost certainly be arriving in Havana…and what a great way to be welcomed to Cuba. It’s one of my favourite cities in the world, I just hope it doesn’t get flooded with thousands of people visiting on cruises each day. I wrote a separate post about Havana which you can read about soon.

Havana Travel
Havana Streets
Cuba Havana Travel
Old cars lined up ready for city tours

Viñales Valley

We left Havana and drove to Viñales which is located in the Viñales Valley about two and a half hours drive west of Havana. Viñales Valley is a UNESCO World Heritage Site that has some of Cuba’s most beautiful landscapes. The music, arts and traditional crafts of the valley are the result of influences from the indigenous people, Spanish colonizers and African slave laborers who used to work in the tobacco plantations. The area is full of lush tobacco fields and valleys where you can hike up mountainsides, go horseback riding and swim in natural waterfalls and rock pools. You can even go cave tubing or zip lining.

Viñales Valley
Viñales Valley

The town of Viñales is fantastic but I highly recommend getting out into the countryside and especially the caves and tobacco plantations. We did a tour that combined a walk through the countryside to see the tobacco plantations and then to a cave big enough for us to swim in.

Speak like a local: The ‘ñ’ in Spanish is pronounced like the ‘ni’ in onion. Examples are mañana and Viñales.

Playa Giron – The Bay of Pigs

Bay of Pigs Cuba
Coco Loco at The Bay of Pigs

The quickest way to head south from Viñales is via Havana but we preferred to see something new so headed for the longer route through Batabano. We stopped at a few small villages before getting lost and having some drunk locals screaming La Juila at us hoping to get a lift.

Playa Giron, or more commonly known as the Bay of Pigs, is a secluded beach that was the site of an attempted invasion by the US during the Cuban Missile Crisis in 1961. The town and beach are quiet and there’s a small museum about the failed US invasion attempt which is referred to as the US’s first defeat in Latin America. If you’re on a shorter timeframe and not a big history buff then you won’t miss out on much if you skip Playa Giron.


Cienfuegos is another picturesque town in Cuba in between Havana and Trinidad. The city is known for its French colonial architecture, as well as its bay front promenade; the Malecón Cienfueguero. Cienfuegos was named after Jose Cienfuegos a General of Cuba in the early 19th century. The town is home to a number of museums and art galleries.

After a short stop in Cienfuegos we headed south towards Trinidad. The drive is just over an hour but we managed to take a wrong turn and had to do a u-turn. As we were doing the u-turn we hit a concrete block, no idea why it was there, but it was big square piece of concrete. We were able to keep driving but not for long. The car eventually overheated and we were stuck on the side of the road, no phone signal, no internet, no idea what to do. We eventually arranged to have the car towed to a mechanic in Trinidad who told us the car was beyond repair. The car rental company sent us a replacement and we were glad we bought the extra insurance.

Cienfuegos Cuba
View over the main square of Cienfuegos

Everything is an experience in Cuba. While we were trying to work out how we contact the insurance company and speak to the mechanic we met so many people that offered to help. Strangely many of them told us that the mechanics wife was having an affair, but he didn’t know. By the time the replacement car showed up we were well across the gossip of the town. The locals, the mechanic and especially our hosts from the Casa Particular were extremely helpful.


The town of Trinidad was a highlight for me, the cobblestone streets and colonial buildings make this place extremely picturesque, you can feel the history of the place as you walk through town. Plaza Mayor is located in the city center and has a fountain in the middle, surrounded by colourful colonial buildings. La Casa de la Musica is a venue in the plaza where live salsa bands play in the evenings. You can sit on the table and chairs or the steps of the plaza to watch.

Trinidad Cuba Travel
Trinidad Streets

We went to Discoteca Ayala which is a nightclub in a cave, although well-known this place would be very hard to find if you weet just walking by on the street. Once you walk down the entrance stairs it’s as impressive as you would imagine, a nightclub in a cave with lights, music, a bar and dancefloor. Drinks were reasonably priced and the place was filled with locals and foreigners of all ages.

Playa Ancon

Playa Ancon Cuba Travel
Playa Ancon

Playa Ancon is a white-sand beach with crystal clear, warm water just 15 minutes away from Trinidad and was one of the nicest beaches we saw on our three-week trip across Cuba. The beach is on the long Ancon Peninsular so it’s easy to find a quiet spot if that’s what you’re after. There’s plenty of food shacks nearby to grab lunch or snacks but if you’re looking for a fancy lunch you can head to the restaurant in the nearby hotel. Playa Ancon was the only time we were offered drugs in Cuba which was the opposite of Central America where 6 Aussie backpackers seemed like a magnet for offers of whatever you want.

Playa Ancon is a white-sand beach with crystal clear, warm water just 15 minutes away from Trinidad and was one of the nicest beaches we saw on our three-week trip across Cuba. The beach is on the long Ancon Peninsular so it’s easy to find a quiet spot if that’s what you’re after. There’s plenty of food shacks nearby to grab lunch or snacks but if you’re looking for a fancy lunch you can head to the restaurant in the nearby hotel. Playa Ancon was the only time we were offered drugs in Cuba which was the opposite of Central America where 6 Aussie backpackers seemed like a magnet for offers of whatever you want.

Playa Ancon
Playa Ancon

Topes de Collantes

Topes de Collantes is one place we missed as we were in a tow truck when we passed it. The nature reserve is 30 minutes north of Trinidad and has waterfalls, hiking trails, and caves.

Scuba Diving at Jardines de la Reina

Cuba has some of the best scuba diving and snorkeling in the Caribbean due to its clear waters and diverse marine life. There are a number of dive sites located around the island, including the Jardines de la Reina, an archipelago off the south coast of Cuba that is home to coral reefs, mangroves, and over 500 species of fish. Jardines de la Reina appears in the documentary Castro’s Reef (see resource section for the link) as he once used it as his personnel diving location.

Santiago de Cuba

Cuba’s second largest city has a slightly different vibe to the capital but retains the colonial traditional feel. The city was the birthplace of the Cuban revolution when Fidel Castro and his fellow revolutionaries attacked the Moncada Barracks in 1953 changing the path of Cuba until today. You can tour the barracks and learn about how Fidel recruited and organised his troops in the areas surrounding Santiago de Cuba.

Santiago de Cuba
Santiago de Cuba

As tourism continues to grow in Cuba you’ll need to head further away from Havana, Viñales and Varadero if you want to escape the crowds. The southern side of Cuba is ideal for this as you’ll see much of what you can find in those more touristy places. We had a great time and met some of the most interesting characters while in Cuba.

Cuba Tourism

The world-famous Bacardi Rum had its original factory in Santiago de Cuba and you can tour the old factory and learn the interesting story of how the owners fled the country during the revolution. Fidel and his Cuban revolutionaries seized the Bacardi assets and forced them to leave the island. Many reliable sources report that the Bacardi family funded multiple assassination attempts against Fidel. This is the reason why Havana Cuba rum is the main rum in Cuba and there’s hardly any Bacardi.

Did you know? Don Facundo Bacardí, the Spanish founder of Bacardi, discovered a colony of bats living in the rafters of his rum factory which was the inspiration for the Bacardi Rum logo.

Varadero and Somewhere Along The Way

After flying from Santiago de Cuba back up to Havana we got a bus out to Varadero. It wasn’t high on our places to visit in Cuba but it’s always on the Cuban travel lists so we squeezed it in on our last couple of days in Cuba. Located on the Hicacos Peninsula, just over 2-hour drive from Havana, Varadero is a beautiful stretch of white sand beach with crystal clear turquoise water and plenty of touristy beach bars and restaurants which feel like you’re in another part of the Caribbean.

Cuba Varadero

After spending the day in Varadero we decided to find a more authentic place to stay instead of the touristy resorts. We took a bus going to Havana and got off randomly along the way before ending up at a small beach town. We found a guesthouse that was hosted by an interesting young guy who seemed to have the latest watch, shoes and expensive brand clothing which we hadn’t seen in Cuba up until that point. We went to our room, then went to the kitchen area to ate some fruit we had. When we were ready to go out we couldn’t leave. The guesthouse was completely locked. We were going upstairs, downstairs, checking all doors, windows etc. but nothing would open. Finally after an hour the guy comes back and we let him know we couldn’t get out. He apologised and told us there’s no way in or out without a key. Again very strange in Cuba.

It’s easier to Travel to Cuba than Ever Before

Traveling to Cuba is an incredible experience that will stay with you long after your trip has ended. Visiting Cuba feels like being thrown into another world so whether you have a few days or a few weeks you will be able to experience Cuban life and culture. The situation is constantly changing and Cuba is becoming more and more accessible. This results in easier travelling but also more tourists which will slowly change Cuba, so go sooner rather than later.

Personally I hope the Cuban society can be brought into the 21st century but I also hope the Cuban way of life, architecture, music and authenticity remains. Maybe there’s a place for international resorts, casinos etc. but perhaps its best to keep them to just a few places. After all, the perceived international influence in Cuba was the catalyst for the revolution.

Travel Resources for Visiting Cuba

Castro’s Secret Reef – Documentary about how Castro used Los Jardines de la Reina as his private reef
Viator – Huge selection of activities, tours and experiences with great cancellation and price match policies.
Get Your Guide – Great selection of experiences from sea, land and air.
SkyScanner – The best place to start looking for flights. They compare prices from a huge amount of airlines.
Hostelworld – Thousands of hostels with millions of reviews. You can also contact other travelers before you arrive.
Travel Insurance – None of us plan to fall off motorbikes or break a leg snowboarding but if it happens make sure you’re covered. – One of the best accommodation booking pages available. This is my benchmark before searching for a better deal (which often can’t be beaten).
AirBnB – Huge range of home to rent across the globe and discounts for longer stays. – The best site for renting cars while travelling, they find the best rates and provide great insurance options.

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