The best of Cuba in two weeks

The best of Cuba in two weeks

The best of Cuba in two weeks
The best of Cuba in two weeks

The best of Cuba in two weeks

The best of Cuba in two weeks

In this article, I’ll share with you what I think could be an excellent itinerary for a 2-week holiday in Cuba starting in Havana. Finding The best of Cuba largely depends on who you are, your interests, and travel style, and who you travel with. I’ve tried to find some middle ground. A best of Cuba itinerary that could work, with minor tweaks, for couples, solo travellers, or families alike.

In terms of budget, you’d need around 1.4k per person, but this too can be optimised depending on your accommodation choices.

My idea of a best of Cuba itinerary combines a bit of everything to allow visitors to experience as much as possible about Cuba: world class beaches, areas of outstanding natural beauty, vibrant cities, and cute little colonial towns. With that in mind, I’ve chosen:

  • Havana, Cuba’s capital and one of the most captivating cities in the world
  • The Valley of Vinales, for its dramatic landscapes and sheer natural beauty. Also the land of the iconic Cuban cigars
  • Cienfuegos, a charming coastal city with uncharacteristic architecture and lots of character.
  • Trinidad, one of the oldest and best-preserved colonial settlements in Cuba, perhaps in the Americas.
  • The beach: Varadero or Cayo Santa Maria. The choice is a matter of personal preference. Will talk more about this later.

The combination of these 5 locations in Cuba is what I’d call, the Cuban magic mix. It highlights a little bit of everything Cuba has to offer: great outdoors, fantastic beaches, vibrant culture, rich history, and lots of traditions.

I’ve not only chosen these five destinations for their beauty for a Best of Cuba itinerary. I’m also taking into account practicalities.

Distance between locations and quality of transportation links

Upon seeing Cuba on a map, many travellers are tricked by the illusion that Cuba is a small island. In fact, Cuba is in length roughly the size of England, and it would take a good 20-something hours to drive from one end of the island to the other.

It is important to take this factor into account when planning your Best of Cuba holiday. Trying to cover too much in one trip might leave you exhausted rather than rested and relaxed, which is the whole point of a sound holiday plan.

The transport links between Havana, Vinales, Cienfuegos, Trinidad, and Varadero or Cayo Santa Maria are some of the best in Cuba. Most of the journey between points is covered by the national motorway, or good quality roads (at least by Cuban standards). With the exception of the trip from Vinales to Cienfuegos, most other legs of the journey can be completed in under 3 hours, or less.

Best of Cuba itinerary on the map

Quality Accommodation

The best hotels and resorts in Cuba are located in Havana and in beach destinations. Outside these tourist hotspots, you need to know what you are doing to find good quality accommodation. My take on a Best of Cuba trip takes this factor into account. I’ve chosen places where travellers are able to find, with our help, anything from authentic B&B experiences to luxury five-star boutique hotels.

Best of Cuba Itinerary. Hotel Parque Central, Havana, Cuba


  • Iberostar Parque Central
  • Iberostar Grand Packard
  • Kempinski Manzana
  • Sofitel Paseo del Prado
Best of Cuba Itinerary. Hotel Central Vinales, Vinales Valley, Cuba


  • Villa Jorge y Ana Luisa
  • Hotel E Central Vinales
  • Casa El Porry
  • Horizontes La Ermita
Best of Cuba Itinerary. Hotel Palacio Azul, Cienfuegos, Cuba


  • Hotel La Union
  • Hotel Jagua
  • Melia San Carlos
  • Villa Lagarto
Best of Cuba Itinerary. Hotel Iberostar Trinidad, Cuba


  • Iberostar Trinidad
  • Brisas Trinidad del Mar
  • La Casona
  • Casa Jorge Mendez
Best of Cuba Itinerary. Hotel Iberostar Varadero, Cuba


  • Iberostar Varadero
  • Melia Varadero
  • Royalton Hicacos
  • Blau Varadero
Best of Cuba Itinerary. Hotel Iberostar Ensenachos, Cayo Santa Maria, Cuba

Cayo Santa Maria

  • Iberostar Ensenachos
  • Grand Memories Santa Maria
  • Melia Buenavista
  • Playa Cayo Santa Maria

I’ve also picked this itinerary based on the breath of activities visitors can engage in. If you are anything like me, planning ahead a good couple of activities for my holidays is just as important as choosing the right accommodation. Some of the experiences I’d recommend for a trip like this include:


  • Classic American Car Tour of Havana
  • Colonial Havana Walking Tour
  • Rum and Cigars Excursion


  • Cueva del Indio (cave system with underground river)
  • Horse Riding
  • Tobacco plantations excursion


  • City walking tour
  • Bay of Pigs and Crocodile Farms
  • El Nicho Waterfalls


  • City Walking Tour
  • Visit to Sugar Mills Valley
  • Ancon Beach


  • Catamaran trip to Cayo Blanco
  • Interaction with Dolphins
  • Hicacos Natural Reserve

Cayo Santa Maria

  • Snorkelling, diving, or boat trip
  • Visit to Remedios, off-the-beaten-track colonial village
  • Day trip to Santa Clara, the Brighton of Cuba

The best of Cuba in two weeks. My personal account

I completed this “best of Cuba” itinerary a while ago with a rather difficult group: My wife and I (early 40s), my kid (1 year old), my sister (15 years old) and my parents (mid 60s). I guess you would agree it doesn’t get any harder than this!

Despite the vast disparity in age groups and interests, we had a great time and would recommend it to anyone, hopefully travelling with a more homogeneous group 🙂

We book the direct flight London to Havana with Virgin Atlantic. More expensive than flying via Spain or Amsterdam, but we went for the direct flight as flying with kids can prove a bit stressful.

In Cuba, I went for a self-drive holiday. Rented a 12-seater through Travelisto and went on the road with the whole family.

In Havana we stayed 3 nights at Sevilla Hotel. Not the best in Havana for sure, but well located and within my budget. Very close to two really good restaurants in Havana: Ivan Justo Chef, and Cinco Sentidos. The original daiquiris at Esto no es un Café were epic!

In Vinales, we stayed at a local B&B, Villa Silvia. We spent two nights there exploring the tobacco plantations, horse riding, went to the Indio Cave and  Mural of Prehistory, and bathed in the river. My kid loved it!

We skipped Cienfuegos and went straight to Trinidad. Stayed for three nights in a Casa Particular, Casa Jorge Mendez. The hosts were extremely welcoming and friendly. We had some of the best meals of our trip at their B&B. Visited nearby Ancon beach and spent the afternoons visiting the local artisan markets, sipping cocktails at La Canchanchara, or listening to music at the main square.

After a bit of discussion, we chose Varadero over Cayo Santa Maria. My personal preference was the Cayo, but finally decided for Varadero because of its proximity to Havana for the return trip. We stayed at the Iberostar Varadero. Everyone loved it, except my wife who isn’t a fan of all-inclusive resorts. However, after staying over the years at many all-inclusive resorts in Cuba and elsewhere, I can confidently say the Iberostar Varadero is one of the best, if not the best, I’ve stayed in. Even the food at the buffet restaurant was good, and the Japanese restaurant was really great.

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