Highlights of Cuba: A 14 day itinerary

Whilst the likes of Ernest Hemmingway could spend years in uber cool Havana sipping Cuba Libre’s or daiquiri’s in Cuban bars writing American classics, the rest of us do not have the luxury of time. If that is the case, I have  provided my take on how to see the highlights of Cuba in just two weeks. If you have more than two weeks you can spend your days sipping drinks in Havana, dancing away in super cool Trinidad or you can even go further afield to Cuba’s second city Santiago de Cuba, which unfortunately we did not get a chance to visit.

 Day 1-3: Havana

Arrive in Havana and step back in time, from the stunning architecture to the vintage cars. Spend at least a day just getting lost in old Havana. Walking through old Havana is like being transported to a place where the past comes alive. Walk along without a route or an end destination. Take in the beautiful sun, city, architecture, cars, bars and cafes. Stop along the way in one of the many bars to cool yourself down with a Pina Colada. Have lunch and dinner in one of the many Paladars (a “private” restaurant in a Cubans home). In the evening sit outside in one of the many squares watching Cubans and tourists alike go about their day sipping strong Cuban coffee or one of the many cocktails (Virgin or otherwise) from the countless bars and cafes. Don’t worry about seeing any of the sites today. Just walk around and take in all that Old Havana has to offer.

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vintage car with a back drop of stunning architecture

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Another example of the quintessential stunning architecture in Havana                                    

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Just another day smokin’ and reading                                          

The second is a day you can spend seeing the sites Havana has to offer.

Some of the many Havana attractions are:

  • Plaza de la Catedral: The Plaza de la Catedral is the most famous cathedral in Havana. It is located in a stunning square with lots activity. It is a tourist hotspot but well worth seeing this stunning Cathedral
  • National Museum of Beautiful Arts of Cuba: Cubans love Art and you will see various pieces of Art everywhere. For those artistically inclined then this is definitely a place to visit.
  • Plaza Vieja (Old Sqaure): The most famous of many squares in Havana. A vibrant place to have a drink and people watch. There are many famous squares in Old Havana and I suggest you try to visit as many of them as time allows, each has something unique and different to offer!
  • The Capitolio: The Capital building is another example of the stunning architecture that Havana has to offer. It is located off a main street and a great place to photograph the stunning vintage cars now used as Taxis.
  • Plaza de la Revolution: Slightly far from Old Havana but well worth a visit. A huge square where the Cuban Government Ministries have all their offices. Worth a visit but will be very different to the Old Havana squares you will now be accustomed to – far away from the famed architecture these have a more Soviet era industrial feel to them.

This is a short list of some of the sites to visit in Havana, however Havana is best seen by exploring off the beaten track. Take a walk from these main sites and just take in the Cuban Culture and sights.

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A ride in one of these taxis is a must                                              
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The Iroko tree -religiously significant for the Yoruba
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Who needs marvel when you have history on your side
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You could spend the day people watching in one of the many squares Havana has to offer

Day 3: Take a tour of Havana in one of the many Classic American cars, or better still, hire your own car and see the city for yourself. A good place to visit is the Chocolate Museum/cafe in Old Havana and try some delicious chocolate shaped in weird and wonderful things. See some other sites or visit museums such as Museums of the Revolution or Museums of Decorative Arts.

Day 4-6 Vinales Valley

Welcome to the Cuban countryside and what a beautiful countryside it is. Just take some time to take in the beautiful views.

This is where you can relax, enjoy Cuban hospitality, smoke cigars farmed in the valley and enjoy the beautiful countryside that is Vinales Valley. Spend at least couple a days enjoying this lovely spot.

Things you can do around the area include taking a walking tour of the main village, visiting farms where tobacco is grown and cultivated for the world famous Cuban Cigars, hike or bike the rural countryside where you will not be disappointed with the stunning scenery. If you have some free time or are feeling a little more adventurous then Cayo Jutias is the perfect location. A secluded and picturesque beach situated on a small island connected to the mainland by a man made causeway. If beaches are your thing then Cayo Jutias will not disappoint.

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Lunch in the middle of a cave, as you do 
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Yes that is a painting on the mountain
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Stunning views of the Vinales Valley from one of the many hill top viewing points

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Top tip 1: Instead of staying in a hotel why not stay in a Cuban Home stay. The main village is situated with literally hundreds of rooms in the main village in Cuban homes which you can rent for very reasonable prices.

Top tip 2: Hire a bike and cycle the local countryside. However please note that this is a valley meaning that there are very steep hills which you will need to take into consideration. If you are up for the challenge then its a great way to see the area.

Top Tip 3: The Vinales farms are a great place to buy authentic Cuban cigars – made directly from the farmers and at very reasonable prices – you can also get a demonstration of how they’re made and try before buying!

Day 7-8 Cienfuegos

A stunning French colonial town and as a result has a slightly different feel to the other cities in Cuba. The architecture has a lot more French influence making it distinct from the rest of Cuba.

I felt that Cienfuegos had a really chilled out vibe and can be a very relaxing stay. Wander around the town and allow yourself to get lost- don’t worry as its a small town you will always be able to find your way back.

In the evening spend the night like the locals sitting along the ‘Malecon’ (sea front) which is a very Cuban thing to do and great way to while away the evenings.

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A beautiful building in a beautiful town

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Top Tip: Have dinner at “Dino’s” the government owned pizza chain. It is a quintessential Cuban government owned ‘fast food’ chain with some good pizza at very low prices. This was one of my favorite restaurant experiences  in Cuba.

Day 9-11 Trinidad

Welcome to the uber cool city of Trinidad. Now I did not have the chance to stay in Havana that long so I think its unfair to compare but Trinidad was my favorite city on my visit.

Trinidad is very unique, a well preserved Spanish Colonial town where you can marvel at the beautifully colourful streets and look up to the high wooden louvers of this 200 year old city and get lost in a bygone age.

The best way to discover Trinidad is just relax your way through the city and dance your way through the night. Its a beautiful city just waiting to be discovered and with many unique aspects this city will be loved by so many people for so many different reasons.

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Sometimes everything seems vintage in Cuba 
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The less glamorous but still vintage Lada cars

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The colourful cobbled streets of Trinidad   

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Chillin’ on my break


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Things to see and do in the city include, but are definitely not limited to:

  • Walking around the town getting a feel of the city, taking in the architecture and people watching
  • Visit the main squares of Plaza Mayor and Iglesia Parroquial de la Santisima. The main Cathedral to you and I – also a great spot for watching locals go about their daily lives.
  • Visit the live band and music show on the main steps of Trinidad in the evening where you can enjoy some great Salsa music and wonderful atmosphere.
  • Take a half day tour to Valle de los Ingenious and learn about Trinidad sugar and slave history.
  • Learn about a religion you probably are not too familiar with (Yoruba) and visit the Santeria Israel.
  • Take a vintage taxi tour around the surrounding area. You will not be disappointed with the city or the taxi experience.
  • There are plenty of museums to cater for different interests – just take your pick!

Day 12 – 13 Santa Clara

The spiritual home of the great Che Guevara. A small town with a big history, known for battle of Santa Clara where Che Guevara conquered the city marking the end of the Batista regime. A trip to the Che Guevara Museum is a must to learn about Che Guevara and visit his grave -this was a definite highlight of our trip.

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A statue outside the Che Guevara’s mausoleum
The architecture just kept getting better in Cuba  



For the rest of your days just relax in the small city and take in the atmosphere of Santa Clara. If you have time then check out the University as it is Cuba’s second most famous university. Something we would have loved to do but did not have time.

Day 14 Havana

Head back to Havana where you can catch your return flight or spend the extra days exploring the beautiful city.

Please Note:

  • I have intentionally left the beach resort city Varadero out of the itinerary because, in my opinion, this not real Cuba and just another all inclusive holiday destination which you can find many like these in the Caribbean. However, apparently they do have pristine beaches so if that’s your thing then add it to your trip just be aware that it is very different both in governance and atmosphere from the rest of Cuba.

We hope you find this useful and feel free to add your highlights of Cuba in the comments section!

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