Two Weeks in Cuba – Itinerary and Tips

Havana - 2 weeks in Cuba itinerary and tips

Before I arrived in Cuba with my friend, we had the idea of travelling the entire length of the country from west to east. After Havana we’d head west to Viñales and from there we’d make our way to Baracoa with the view of stopping at various cities and towns in-between.

However, when we arrived we discovered two weeks in Cuba was not enough time and it would be better and much easier to concentrate on the western half of the country where most of the places we wanted to explore happened to be located anyway.

As a result of changing our initial plans, we scrapped the idea of going to Santiago de Cuba and Baracoa since it would involve a 12-hour bus journey from Trinidad, and a further 4.5-hour journey to Baracoa from Santiago de Cuba. We didn’t mind those journeys but we didn’t want to duplicate the mission back to Havana.

If you have more time you could add them to this itinerary, alternatively, it’s worth checking how much flights cost for the journey back to Havana or Varadero.

Itinerary Breakdown
3 nights Havana
4 nights Viñales
1 night Cienfuegos
3 nights Trinidad
1 night Santa Clara
2 nights Varadero


2 weeks in Cuba travel itinerary and tips

Afro-Cuban jazz blaring from place to place, crumbling buildings, eclectic architecture, brightly painted facades, sexy sultry bodies, tequila at noon, dusty old streets and those old vintage cars. Havana hits the senses like nowhere else in the world.

Havana - 2 weeks in Cuba, itinerary and tips.

Local culture - 2-weeks in cuba, travel itinerary and tips.

Things to do

  • Walk along the Malecon sea drive
  • Learn more about Cuba’s revolution with a visit to the Museo de la Revolucion
  • Head to revolution square where you’ll find huge artworks of Fidal and Che. These are one of many, many pieces of public artwork paying homage to Cuba’s most famous political figures
  • For a quick tour of Havana hop on a rickshaw to see the city highlights whilst listening to Cuban music blaring from a mini radio. It’s touristy but great fun. Make sure you agree on a price beforehand and don’t let your guide exceed the duration you agreed upon or you’ll end up paying more than you wanted
  • Mix literature and cocktails with a pit stop at Hemingway’s favourite bars, La Floridita and La Bodeguita del Medio

Where to stay
Budget: Since we needed accommodation for our first nights in Havana to obtain the tourist Visa we booked an AirBnb and took a taxi directly there from the airport. Our host, Eduardo was super nice and welcoming, a great introduction to Cuban hospitality!
Splurge: Although I didn’t stay here myself, I would loooove to have stayed at Hotel Ambos Mundos. At the risk of going overboard on the literary theme (if that’s even possible for literary lovers?!) this is also where Hemingway chose to stay when he was writing and finished his book Death in the Afternoon (1938) among these very rooms. Awesome, right?

Where to eat and drink
Whilst I didn’t have much luck in Havana on the food front, there’s certainly no shortage of good places to drink. Already noted, head to Hemingway’s favourite watering holes, La Floridita and La Bodeguita del Medio for a cocktail or two. If you’re looking to party all night, shimmy on over to Tropicana for the whole shebang.



Horse riding in Vinales, Cuba

To miss this place out from your trip would be a mistake. Exploring the natural beauty of Viñales, with its soaring limestone cliffs and lush flora and fauna, is something all visitors to Cuba must do.

Things to do

  • Horse riding
  • Hiking
  • Cycling
  • Check out the brightly painted Mural de la Prehistoria
  • Cueva del Indio – motor boats now operate a short tour along the underground river through the cave
  • Have fun in the picturesque town centre with its many colourful casas and lively bars and restaurants. It’s definitely catered for tourists, but after  a day of nature-based activities, maybe you won’t mind letting your hair down with a mojito in hand. If you’re feeling brave accept the invite to dance with some of the locals – you won’t surpass their natural-born moves, but it’s a good way to learn how to do it from the professional!

Where to stay
Budget: Homestay at Casa de Marilyn is a great place to stay for a variety of reasons. The hosts speak excellent English and are happy to organise any day-trips and activities you desire. The breakfast is superb and it’s located on a peaceful street yet just a few minutes walk to the main strip in Viñales with all the bars and restaurants.
Splurge: If you want to stay in one of Cuba’s most quintessential colonial-style hotels with its stunning pastel-pink exterior and breath-taking views then Hotel los Jazmines offers exactly that.



2 week travel itinerary in Cuba

Good advice usually comes from first-hand experience. So when my friend, Emma, suggested I stop off at Cienfuegos for a night before heading to Trinidad because she enjoyed her time there, I quickly factored it into my itinerary. Located on the foot of a bay, Cienfuegos has a delightful mix of seaside appeal and the buzz of a small city.

Things to do

  • Palacio de Valle
  • Walk along the Melacon
  • Stroll to the neighbourhood of Punta Gorda
  • Day trip to see flamingoes in flight at Laguna Guanaroca
  • Day trip to El Nico waterfall.

Where to eat and drink
If you’re not staying at Hotel La Union you should still enjoy a mojito inside the beautiful courtyard or by the illustrious pool.

Where to sleep
Budget: Yanelis & Kiki. This place is chinzy (understatement), think polyester curtains and bedding but there’s a roof top terrace and breakfast area. There’s also air con and fridge to combat those inevitably hot and sweaty nights. However, the best thing about this casa is the short walk from the centre of town.
Splurge: If you want to something fancy, stay at Hotel La Union which is slap bang in the middle of this pretty harbour-side town. The building is certainly a statement with its striking white and blue exterior and French colonial decor. It would be anyone’s first choice of accommodation if money wasn’t an issue. It’s beautiful.



Old Town in Trinidad - two weeks in Cuba, itinerary and tips

The UNESCO World Heritage Site of Trinidad, Cuba, is the perhaps the most beautiful city in the whole of Cuba, with its higgledy-piggledy cobblestone streets and colonial architecture found nearby the Plaza Major.

Cycling from Trinidad to Playa Ancon - 2 weeks in Cuba, itinerary and tips.

Things to do:

  • Hire a bike and cycle to Ancon beach, the journey passes some stunning scenery. It’s approximately 12km from Trinidad and will take you 45-1h each way depending on your fitness – and how good the bike is!
  • Hike through the forests of Guanayara National Park until you get to a beautiful waterfall and natural pools for you to bathe inside or simply dip in your toes to cool down before the uphill hike back through the park
  • Snorkelling at Playa Aguiliar or Ancon
  • Explore the beautiful Old Town, including Plaza Major, stunning colonial architecture and a variety of museums

Where to eat and drink
Just as we had resigned to the fact that our taste buds would be deprived of all joy during our time in Cuba, a visit to Sol Ananda restored all hope. The food, drinks, service exceeded our expectations, and I can’t tell you how good it felt to finally have a really good meal at a restaurant in Cuba. It’s French colonial decor complete with 1920s chandelier and furniture is certainly pleasing on the eye (it was no surprise for us to hear the owner is also an architect).  We could happily have eaten here every night but it was also the most expensive place, so we managed to resist temptation by restricting ourselves to only two visits.

For a younger vibe and cooler atmosphere head to La Redaccion, named after the first newspaper in Trinidad. The decor reflects the theme so you’ll find quirky little objects and paraphernalia that you’d usually find in a newspaper room. The menu also offers vegetarian options which I found to be rare in Cuba. Even if you only go for drinks, the atmosphere of this place should not be missed, it’s a real gem.

We also had dinner at Trinidad Colonial one night, I recommend eating or having a few mojitos on the rooftop terrace. You’ll find a few Cuban dishes as well as the usual fish and chicken dishes. A tree grows through the middle of the restaurant and all the branches elegantly meander across the terrace which makes it look super pretty and summery.

N.B Please don’t be tempted by the patterned murals and pretty decor of El Figue. The food and service make a trip to McDonalds appear like paradise. Ruchi ordered baby squid and it looked like someone had butchered satan on her plate. No jokes.

Where to sleep
Budget: I don’t want to recommend the place I stayed in, because it wasn’t a very nice experience. You can read about my troubles here if you’re curious. Instead, I recommend Hostal Marledy Y Miguel as I spoke to some other travellers who stayed at this place and said their host was lovely. It’s located in the historical centre so you’ll have everything on your doorstep.
Splurge: If you’d prefer a hotel, then Iberostar Grand is the best in town.


Santa Clara

Santa Clara - Two weeks in Cuba., itinerary and tips.

There isn’t that much to do in Santa Clara, that’s why it only needs one night. It’s not as beautiful as Trinidad and it doesn’t really have that holiday vibe that the rest of Cuba has in the shed load. However, it’s a student city with a young energy. The most notable aspect of Santa Clara is its association with Che so you’ll find lots of references to him around the city.

Things to do

  • Head to the Che Museum and Mausoleum
  • Fábrica de Tabacos Constantino Pérez Carrodegua – tabacco factory
  • Do a salsa class
  • Catedral de las Santas Hermanas de Santa Clara de Asís

Where to eat and drink
Cafe-Museo Revolucion is filled with lots of Che paraphernalia , including many, many photos in all shapes and sizes hanging from the wall – a great place to come for some fuel and fun!

Where to sleep
I had such a wonderful time staying at Hostal Caridad 5 that I wouldn’t even want to recommend staying anywhere else. Even after hurricane Irma had struck out the electricity on the first night, they prepared a stunning dinner by candlelit with copious amounts of food and no question seemed too difficult for them to answer or help us with. Such a gracious, beautiful family and a lovely home to be with for any length of time.



Because I ended up getting caught up in the chaos of hurricane Irma, my friend and I didn’t really get to see much of Varadero. But if you just want to relax for a couple of nights and do nothing but sunbathe before returning home, then you’ve come to the right place.

Alternatively, if staying in a resort or the whole lazing on a beach doesn’t sound appealing to you, I recommend going back to Havana for more of that spirit-lifting energy which you’ll certainly miss when you leave Cuba and head back to ordinary life!

Are you planning a trip to Cuba? If you have any questions, ask in the comment box below!

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'Two Weeks in Cuba – Itinerary and Tips' have 2 comments

  1. October 14, 2017 @ 4:51 pm Isaac

    I’m going to Cuba soon and have received the tourist visa, but someone said I also have to pay a tax at the airport when leaving Cuba and that it was a huuuge queue to do so. Did you had to do this, and if so, do you now if this is something we can pay before arriving to the airport?


    • October 17, 2017 @ 5:18 am Shing Yoong

      Hi Isaac, I was also told I’d have to pay a tax of approx £25 too. However, when we arrived in the airport on the way back we were told we didn’t have to pay it. Unfortunately I can’t tell you whether this is normal procedure of not or not – I just felt lucky it wasn’t the case for us and I hope you too!

      Tip: The airports in Cuba are teeny-tiny so make sure you buy any souvenirs beforehand and bring snacks and something to read for the wait!


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