2 weeks in Cuba – Travel Itinerary

2 weeks in Cuba - Travel Itinerary

Nobody should make the mistake to reduce Cuba to just another Caribbean vacation destination. Honestly… don’t. Cuba is much more than that… Believe me, if you plan your stay in Cuba independently on your own and if you don’t stick to Varadero, Cuba will quickly take its place in the list of your most favourite destinations. It is on top of mine!

In this blog post I want to help you planning your travel itinerary to enjoy all facades of this beautiful country.

2 weeks in Cuba - Travel Itinerary Map

3 days in Havana

My journey started (and ended) in Havana. The international airport of Havana is maybe the major reason for that but either way Havana is absolutely a must in your Cuba itinerary.

Things to do in Havana
  • Stroll around the Old Town – Havana Vieja
  • Walk down Malecón
  • Visit the neighbourhood
  • Enjoy the beach life in Playas del Este
  • Drink rum or cocktails and long drinks made with rum like Mojitos and Cuba Libre
How to go to Havana

From outside Cuba via air is the most convenient way I guess. Recently a US ferry company started operating regularly from Miami. Within Cuba the major bus company Víazul is operating from and to Havana.

Where to stay in Havana

I stayed at Casa Miriam and Sinai in Havana Centro. The room is clean and the hosts are very friendly and helpful. If they don’t have a room available they would also recommend and arrange another Casa Particular (that’s how B&B is called in Cuba). The double room per night costs 25US$. Write Sinai Sole an e-mail to book a room at sinaisole@yahoo.es. By the way, AirBnB recently enabled their services for Cuba.

2 weeks in Cuba - Travel Itinerary - Havana

2 days in Viñales

I made the mistake not to include Viñales to my itinerary for which I still blame myself. But yet, I have a perfect excuse to visit this beautiful country again.

Things to do in Viñales
  • Go hiking in Valle de Viñales
  • Take a horse-back riding tour in tobacco farms
  • Visit El Jardin de Cuba
  • Learn how to roll a Cuban cigar in a tobacco plantation
How to go to Viñales

The bus drive with Viazul takes not more than 3,5 hours and costs 12US$. You can easily buy your tickets in the bus station in Havana.

Where to stay in Viñales

Since I haven’t stayed here I can not recommend anything personally but you can check TripAdvisor and AirBnB to compare all B&Bs and find the best one for you.

2 weeks in Cuba - Travel Itinerary - Vinales Pinar del Rio

Photo by Ingmar Sörgens

2 days in Cienfuegos

Also one place I missed to explore but only drove by. If the time allows have a stop-over in Cienfuegos before heading south of Cuba.

Things to do in Cienfuegos
  • Take a walk in the colonial city
  • Go swimming, snorkelling and sun bathing in Rancho Luna Beach (20 minutes away from Cienfuegos)
  • Go hiking to El Nicho Waterfalls in National Park Topes de Collantes (2 hours with car for approx. 40US$ roundtrip)
How to go to Cienfuegos

From Viñales directly the bus drive with Viazul takes about 8 hours and costs 32US$. From Havana the drive takes about 5 hours and costs 20US$.

Where to stay in Cienfuegos

Again here the most convenient and budget friendly option is to stay at a B&B. Check TripAdvisor and AirBnB to compare all B&Bs and find the best one for you.

2 weeks in Cuba - Travel Itinerary - Cienfuegos

2 days in Trinidad de Cuba

Trinidad is a “must” in any Cuba itinerary. It is a colourful colonial city where the pace of life is slower than any other place I’ve been to.

Things to do in Trinidad
  • Walk around the colourful city
  • Go swimming in Playa Ancon (only 12 kilometres away)
  • Go hiking to Waterfall Caburni in National Park Topes de Collantes
  • Learn Salsa in Casa de La Musica
How to go to Trinidad

The bus drive with Viazul from Cienfuegos takes less than 2 hours and costs 6US$. From Havana it takes almost 10 hours and costs 25US$.

Where to stay in Trinidad de Cuba

I stayed at Casa de Miriam near to Plaza Mayor. Miriam is an excellent host. She is very friendly and helpful. The double room per night costs 25US$. She serves breakfast (5US$) and dinner (10US$). You have to try her grilled lobster and Mojitos. Write her an e-mail to book a room: casamiriamtrinidad@yahoo.es. Check AirBnB and TripAdvisor for more B&Bs.

2 weeks in Cuba - Travel Itinerary - Trinidad

2 days in Santiago de Cuba

Santiago de Cuba is in the far south end of the island which makes the decision very hard to include Santiago de Cuba to your Cuba itinerary or not. Is the long drive worth it? It very much depends on your interests and how much time you have.

Things to do in Santiago de Cuba
  • Walk around the second biggest city of Cuba
  • Learn about Cuban revolution
  • Visit Castillo de Morro to learn about the Spanish Conquerors
  • Climb the big rock – La Piedra Grande
How to go to Santiago de Cuba

The bus drive from Havana takes about 15 hours and from Trinidad it takes 8 hours. It is also possible to fly from/to Havana with Cuba Jet.

Tip: If you have enough time and want to shorten the distance you drive at once, consider adding Camaguey and Guardavalaca to your itinerary on your way to Santiago de Cuba.
Where to stay in Santiago de Cuba

I stayed at La Casona de San Jeronimo near to city centre. Asela and her mother were excellent hosts. They prepared yummy breakfast and dinner. I felt comfy here and would recommend to everyone. The double room per night costs 20US$. Breakfast costs 3US$. The taxi ride from the bus station costs 2US$. To book a room write Asela an e-mail directly at lacasonadesj@yahoo.es. Also check AirBnB for more options to consider.

2 weeks in Cuba - Travel Itinerary - Santiago de Cuba

2 days in Cayo Largo del Sur

Now if you want to experience pure Caribic and relax doing nothing but sun bathing, swimming and reading, I guess Cayo Largo del Sur which is part of Isla de Juventud is the perfect place for it.

The only downside of it is that the island is reachable only via air with a small propeller with Cuba Jet and it is a tourist zone only for non-Cubans. The fact that me as foreigner being able to visit this beautiful piece of land but the locals are not allowed to, unless they work here, made me feel very uncomfortable after all.

Things to do in Cayo Largo del Sur
  • Go snorkelling in crystal clear blue waters with colourful coral reefs
  • Go on a catamaran tour to see one of the beautiful Caribbean sand banks, spot colourful starfish and see iguanas in one of the small rock islands.
  • Be a beach bummer in Playa Sirena – the most beautiful beach I’ve ever seen till now! As a matter of fact, this lovely beach would be a reason for me to come back to Cayo Largo.
How to go to Cayo Largo del Sur

I might be wrong but the only way to reach this island is via air with a small propeller with Cuba Jet or via boat which is very rare and difficult to get, as far as I’m informed.

Where to stay in Cayo Largo del Sur

The only option is to choose one of the resort hotels. Check  TripAdvisor to get an overview.

2 weeks in Cuba - Travel Itinerary - Cayo Largo del Sur - La Isla de Juventud

If I go to Cuba again…

Well, you already know, Viñales… I added it to this itinerary for you anyway not to make the same mistake I did. Next time I’d add Santa Clara, Camaguey, Guardavalaca and Baracoa.

This time I would skip any touristic zone such as Isla de Juventud and replace it with short day trips to the beach from the cities I visit on my way. Cuba is a Caribic island, so no matter where you are for sure there will be a beautiful beach to bum around.

When to go to Cuba?

As soon as possible! Since the relationship between Cuba and United States gets better slowly, it is very possible to see the respective influence very soon. Which means the prices go up, the places will be filled with tourists and the tourist traps will increase. So hurry up!


For more information about travelling in Cuba read my Travel Guide to Cuba. 

For more insights I recommend Lonely Planet's Travel Guide for Cuba.
traveler packing listDon't forget to check my Pack List for useful travel items.

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Travel Itinerary for 2 weeks in Cuba

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Other blog posts about Cuba

travel guide for cuba things to do in Cuba walking tour in havana vieja cuba Things to do in Trinidad Things to do in Santiago de Cuba - Citizen on Earth Travel Blog

16 Comments on “2 weeks in Cuba – Travel Itinerary”

  1. Thank for such a detailed guide! I am going to Mexico and Cuba as my big annual trip this winter (I follow the same logic that you do re work and travel, only that my job is a bit crazier and takes me to places). Now I know what to do!

    Liked by 1 person

      • 😀 I actually would not mind slowing down on work travel and explore Paris, since I so wanted to live here (and now I am always away). But then I got to see some places where I would not really travel for fun (like Kazakhstan :D). Maybe I can learn some project management from you and can get more of a normal life :))

        Liked by 1 person

      • I wouldn’t mind if my job would take me to Kazakhstan. Lucky you… But yes, I totally understand that being on the road constantly can be tiring too. I also prefer to stay in Hamburg in summer and explore the area around North and Baltic Sea. It’s lovely.

        Liked by 1 person

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