An Epic Cuba Two Week Backpacking Itinerary

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*Updated June 2020*

So you’re looking for a two week Cuba itinerary – I couldn’t be more excited for you to experience this incredible country! 

Cuba is one of the most unique travel destinations in the world. Although travelling Cuba for two weeks will only allow you to visit just one part of this surprisingly large country, it should give you a great insight into this frustrating but totally rewarding destination.

After backpacking through six places, here is my epic Cuba two week itinerary. I’ve also included tonnes of tips and advice to prepare yourself before you go to this Caribbean wonder. Enjoy!

How to include sightseeing in Vinales into a two week Cuba itinerary
The colourful cobbled streets of Vinales

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How to Spend Two Weeks in 1
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best itinerary for two weeks in cuba

What is Cuba like?

Despite being a picturesque 50s time capsule, travelling Cuba isn’t actually that easy.

For a start, the accommodation and food standards are poor, not to mention simple mod cons like the (practically non-existent) internet.

Prices for tourists are obviously inflated and the Cubans’ laid back attitude is often frustrating, especially when you’re used to basic efficiency.

Nevertheless, sometimes the most rewarding and fun trips are the ones that not only challenge you, but also broaden your horizons.

So go on your two week Cuba trip with an open mind and tonnes of patience and you’ll be totally rewarded!

I also found my two weeks in Cuba to be pretty busy with tourists which I wasn’t expecting. 

I guess like me, everyone is frantically scrambling to catch a glimpse of ‘authentic’ Cuban life before modernity and Americanisation seeps into the cracks of the dilapidated buildings, shamelessly turning them into McDonald’s and chain grocery stores!

Planning your trip to cuba

For such an interesting and unexpectedly large country, I can tell you now that two weeks is definitely too short a time to see everything Cuba has to offer. However, 14 days in Cuba does give you a nice amount of time to experience the west half of the island, at least partially.

If you have more than two weeks then I’d definitely recommend flying to the East to see Baracoa, Holguin and Santiago De Cuba. I heard some fantastic things from the locals about the East being the ‘true Cuba’, but sadly I did not have the time myself.

When I flew into Havana, I had no real plan of how long to spend in each destination or in what order to visit them. I genuinely wanted to get swept away in the spontaneity that the Cubans are so well known for. If I found a place I loved, or even better fell in love with Juan the sexy salsa dancing god (wishful thinking) then I had the option of staying longer in a town if I wished.

I would avoid pre-planning/booking most of your trip as being flexible will allow you to have the best and most authentic Cuban experience.

It’s important to realise that in Cuba you’ll never be short of accommodation or transport options so you can be flexible, which is a big weight off any traveller’s mind.

Galleries and souvenirs displayed in Havana in Cuba
Havana’s pedestrian strip with artists displaying their work and souvenirs for sale in Havana

Some useful travel tips for Cuba:

Here are some other important points that are worth knowing before you touch down for two weeks in Cuba:

  • Bank cards – If like me you have a travel Mastercard it won’t work at ATMs (but Visa works fine). With a Mastercard, you are only able to withdraw money inside banks with your passport which can be a bit of a nightmare with restricted opening hours etc. It’s worth checking withdrawing fees with your bank before you leave too.
  • Currency – Cuba has a closed currency so you cannot exchange money in advance. As a tourist you can only get $CUC (Cuban convertible pesos, which is one of two currencies) from a bank or the airport when you arrive in the country.
  • Spending money – I got out about £200 worth of $CUC initially but it felt like it wasn’t long before I needed more cash. I’d suggest first withdrawing £300-£350 and splitting it around your bags for safety. I unfortunately didn’t keep track of my exact spending on this trip. However on a backpacker budget, eating out for at least one meal a day and sharing accommodation, I spent roughly £450 (€505/$630CUC) in two weeks. Cuba is more expensive than you think, so factor in extra spending money.
  • Accommodation – Hotels are not common in Cuba. Instead people rent out their spare rooms in a homestay fashion which are called ‘casa particulars‘ or more commonly shortened to ‘casa‘ (house). This type of accommodation will have a sort of blue upside down anchor sign displayed with the words ‘Arrendador Divisa‘ to show that they are licensed. They are basic but you’ll have a much more interesting experience in casa’s compared to a hotel. However if you would like to pre-book a hotel, take a look at

  • The Internet – Wi-Fi is only accessible in certain places, such as a plaza square or big hotel and only in larger cities. It is controlled and restricted by the Cuban government and isn’t cheap or fast. You will need to buy a green WiFi card from an ETECSA telecoms centre or a hotel that has Wi-Fi. Sometimes entrepreneurial locals will offer to sell you one if you’re in a Wi-Fi area. Although this means you’ll be paying a little bit more, it can be quite convenient. If you’re ever unsure of where the internet hot spots are, I’d just look around to see where there are large groups of teenagers plugged into their phones!
  • Crime – Despite common misconceptions, especially about Havana, Cuba is a relatively safe country. Although the government does not release official crime statistics, gun crime is virtually non-existent and murder rates are one of the lowest in Latin America. As always, you’ll need to be careful with your possessions in case of pickpockets and opportunist thieves (a bumbag/waist bag helps) but I personally saw no cause for concern.
  • Harassment – Expect local people to come up to you in the street and start a conversation. I experienced this three times with men in Havana when I was walking alone. Although my guard was immediately up, it turns out they were simply intrigued to see where I was from and what I was doing in their country. Generally I found the Cuban people really inquisitive and very kind. I didn’t feel threatened once.
  • Solo Travel – I went to Cuba solo yet it wasn’t long before I met people who I then travelled with. In hindsight, travelling alone would have be much more expensive. We shared a taxi between destinations and also accommodation between the three of us everywhere we went. Casa’s are costed on a per room basis, no matter how many people are staying in it. It is extremely common that they will have either two or three beds, so you can see this would be pricey for a single person. If you are travelling Cuba alone and fly into Havana, there are a handful of hostels which I would recommend staying at for a night or two so you have the opportunity to meet others going your route.

For more, check out these useful tips before you go to Cuba.

An epic Cuba two week itinerary with tips and travel advice
Questionably rocking a bumbag in Cienfuegos with the lovely Frenchies I travelled with.

Suggested Cuba two week itinerary:

Below is an outline of places I visited on my Cuba two week itinerary . Again, this is only a guide. Instead I’d recommend following your own flow when you are out there:

Havana – Las Terrazas – Vinales – (Cienfuegos) – Trinidad – Varadero – Havana


(Day 1,2,3)

green pink and blur convertible cars lined up in Havana
Colourful vintage convertibles lining the Malecon.

Havana is overwhelming, beautiful and exasperating in equal measures. But 2-3 days is an ideal length of time to get settled and take in the sensory overload of this bustling and colourful capital.

Things to do in Havana:

  • Walk around the streets getting lost in old Havana, take pictures of the eccentric crumbled buildings and vintage cars and check out the atmospheric main plazas (including Plaza Vije and Plaza De La Catedral).
  • Ride the streets in one of the stunning classic tourist cars that line the Malecon. However be prepared to pay a tourist price for this. You can easily ride in some pretty cool old cars if you simply take a common taxi.
  • If you like art, the Bellas Artes is a lovely modern, air-conditioned art gallery for $8 CUC. It contains not only Cuban art but some very famous work from around the world.
  • Get a cheap taxi over to the Fort Castillo del Morro (roughly $3 CUC) to look around the fort and lighthouse and admire the view towards the city. It’s so quiet and peaceful compared to the city centre. At 9pm every evening tourists can watch a traditional cannon firing ceremony, an interesting performance that has been going on for centuries.
  • The Malecon is where all the musicians and young Cubans hang out at night. Head there after dinner one evening to soak up the atmosphere and salsa with strangers.
  • Check out Fabrica de Arte Cubano, an eclectic venue set within an old factory. The venue combines rotating art exhibitions, lively evening music performances, dance lessons, movies, theatre and good value dining and drinks. Costs $2 CUC to enter.

I’d personally avoid visiting the Revolution Museum. It’s stifling hot, the exhibits are uncomfortable stilted propaganda and it’s generally pretty disengaging. In my opinion, it was not worth the entrance fee.

lighthouse and fort in front of the sea in Cuba
The view over to the lighthouse and Fort Castillo Del Morro
girl sat on wall looking over to Havana
Gazing over to Havana and the fort.


(Day 4)

palm trees at las terrazas national park in Cuba
The jungle of the Las Terrazas National Park.

Las Terrazas is a scenic and serene UNESCO biosphere Eco town situated in the Sierra del Rosario Reserve only an hour and a half away from Havana. If you have time, I would recommend fitting this jungle paradise into your Cuba two week itinerary.

Before you arrive, make sure you book accommodation either online or by phone (your Casa in Havana will probably have contacts). We had problems arriving at the park with no proof of accommodation (despite casa particulars being readily available).

We got up early and arrived here by about 10am so had a full day to explore. It’s a gorgeous place but I wouldn’t spend any more than one or two nights here.

Things to do in Las Terrazas:

  • If you’re good with directions (oh and in Spanish!), hike up to the Che Monument and Mirador for the view (on a clear day anyway – my view was a little foggy!). It takes a few hours and lots of up uphill scrambling off the main path. It is definitely worth the effort though but lots of people get lost.
  • You can combine the above walk with visiting the Banos San Juan (natural swimming pools) on your way back. If not, they make a good half day trip themselves. We nearly got hit by lightening as we walked through the forest to these baths and so spent ages relaxing here to calm our nerves!!
  • Eat at El Romero, a sustainable and organic vegetarian restaurant. Even non-veggies will appreciate the interesting food which is cooked in traditional clay ovens.
girl standing on hill looking out to thick fog
Our not-so-amazing view from the Che Monument!
Vintage car parked in the jungle in Cuba
Our vintage taxi ride from Havana to Las Terrazas


(Day 5, 6, 7)

orange sunset over a field with horses in Vinales, Cuba
Beautiful sunset skies over the fields of Vinales with grazing horses.

Dominated by overgrown jade-coloured outcrops called ‘mogotes’ that perforate the lush farmland, the UNESCO Heritage town of Viñales, only a few hours away from Cuba’s capital, looks like it has fallen straight from a classic Cuban cowboy novel.  I was in love with it the moment I laid eyes on it.

The atmosphere here in Viñales is laid back and stubbornly timeless: farmers cultivate crops using centuries’ old organic methods, horseback is the preferred mode of transport and the colourful houses are lovingly built with local natural resources.

There are tonnes of quintessentially Cuban things to do here and the restaurants are some of the best I experienced on this trip.

Things to do in Viñales:

  • Go on a horse-riding tour organised by your Casa. Your guide will take you to caves and through farms and coffee plantations. It’s a fascinating insight and opportunity to discuss the wider political and social system of Cuba. Farmers have to give the majority of their crop to the government, keeping only a small share for personal use and tourist sales. You are looking at around $50CUC (£36) for a 4-5 hour half day trek.
  • Have a tobacco plantation tour to learn about the classic manufacturing methods of the world famous Cuban cigars. When I did this, I was shocked to see that literally each cigar is hand rolled by the farmer and his family. There are no industrial machines, just nimble fingers and a lot of patience. As part of your experience, you will also get to try a cigar as fresh as it gets. Whereas most shop-bought cigars in Cuba have an average shelf life of 15 years and cost an arm and a leg, the organic ones from this region last 3 years and can be bought for as little as $3CUC (est. £2.40) each. If you want cigars as a souvenir, I would highly recommend you wait until you get to Viñales to buy them fresh and direct from the farmer.
  • The karst landscape in this region has resulted in a maze of intricate caves to explore. Some you can visit on a horse riding tour as previously mentioned, but Cueva del Indio, where you can ride a boat on an underground river, is a half day outing itself.
  • Go to the stunning beach of Cayo Jutias. It’s an uncomfortable and long journey due to the poor roads but the dusty white sand and tangle of mangroves create an utterly relaxing backdrop for a full day of sunbathing and eating freshly caught langoustines. The beach is clean, well maintained and the gorgeous pure water is typical of Cuba’s famous beaches.
  • Eat at El Olivo back in the main town as a treat. The food is cooked by a Michelin Star chef and although rather meat heavy, it is really good. The pizza restaurant in the town is also great and you have plenty of lively bars to choose from at night where they let you pour your own alcohol in cocktails(!)
  • For a small $3CUC (est. £2) entry fee for visitors, you can enjoy the incredible poolside views over Viñales from Hotel Jasmine. You’ll need to get a taxi there but once you arrive there is a massage parlour, occasional poolside live music and a bar/restaurant, ideal for a full day of relaxing.

When you arrive at Viñales, try to avoid accommodation in the centre as you won’t then get to experience the breath-taking rural views.

I stayed at Casa La Cieba and although it provides really basic accommodation, it has stunning views overlooking the countryside and it’s only a 10 minute walk from the town.

white beach and clear water with mangroves near town of Vinales
Pristine white sands, mangroves and aqua water at the stunning Cayo Jutias beach – photo courtesy of TripAdvisor.
horse riding through fields on a Cuba two week itinerary
Tobacco plantation horse riding tour


(Day 8)

girl in dilapidated building in Cuba
Sightseeing in Cienfuegos

Cienfuegos is like the Paris of Cuba. With charming French architecture and a touch of the feisty Caribbean spirit, it’s rapidly becoming a popular spot to visit on the tourist trail.

However be aware that it’s likely you’ll either love or hate this place. It’s much cleaner and calmer than Havana and those who fall in love with Havana may find Cienfuegos boring in comparison.

I spent two days here out of my Cuba two week itinerary and although I thought it pleasant enough, I’d recommend going for just one day. I didn’t feel there was actually all that much to do there other than the following:

Things to do in Cienfuegos:

  • For $2 CUC you can visit the Mirador Jose Ferrer to have a look at the historic house and also the views from the bell tower. There are a few nice art exhibitions near this building which are worth checking out.
  • Walk along the peninsular, stop somewhere for a cocktail and people watch.
  • Visit Playa Rancho Luna, a nice beach 18km away. Palm parasols line the shore which you can under lie for free and there are a couple of bars serving food and drink, including fresh coconuts. If you want to try some fresh fish, look out for the fishermen coming in to shore as they will offer to sell and cook something for you cheaper than a restaurant.

Some people skip Cienfuegos altogether if time is limited, so it’s worth bearing this in mind.

Cuban beach with palm parasols and stormy sky
The characterful Playa Rancho Luna Beach


(Day 9, 10, 11)

kids playing football on cobbled street in Varadero Cuba
One of my favourite pictures from Cuba – kids playing football in the cobbled streets of Trinidad

Trinidad, along with Viñales, was one of my favourite destinations in Cuba.

The cobbled and colourful colonial town is jam-packed with idyllic cultural sights and the surrounding national park is fantastic to explore.

The vibe in Trinidad is authentically Caribbean yet strangely European: there are boutique-like bars and restaurants, art exhibitions and the streets are delightfully alive with music flowing from a combination of buskers, businesses and homes.

Things to do in Trinidad:

  • Check out the independently owned shops, art galleries and the Municiple Museo. The museum has a small tower that you can climb to see breath-taking views over the town, framed by the mountainous countryside in the distance.
  • Take a tour to the Topes De Colliantes National Park nearby. I booked a tour that took you there in a crazy open topped Russian truck. We stopped at a viewpoint (‘mirador’) and a coffee farm, then went on an informative guided walk through the forest to the Vegas Grandes waterfall for a swim. It was an interesting and active day that I’d highly recommend. Alternatively you can do some horse-riding tours through the National Park.
  • Playa Ancon is a lovely beach nearby for an afternoon or full day trip. The sand here is softer than Playa Rancho Luna in Cienfuegos and the water even clearer.
  • By evening, sit on the steps in the main plaza drinking $1.50CUC mojitos with the other travellers. Everyone gathers here after sunset and there’s an awesome atmosphere that kept me coming back every night to make friends, sing and dance.
  • The Casa Del Musica (at the top of the plaza steps) has live salsa music most nights. You pay a small entry fee to enter up but it’s great fun to watch the pros twirling each other around, or you can join in, allowing a local to give you a free lesson. We were fighting off offers from dozens of men by the end of the evening!
  • There is a ‘must-see’ nightclub in a cave called Disco Ayala. Ask around for directions when it’s late, but it’s essentially one road all the way up the hill for 10/15 minutes (Trinidad is built on a gradual incline). It is literally a ‘super club’ with an insane sound system in a massive limestone cave in the middle of nowhere. Be prepared to get soaking wet from the dripping surroundings though. It’s hot and incredibly sweaty but it’s a surreal and hilarious way to end an evening drinking in the main plaza.


(Day 12, 13)

bright white sand and aqua water of varadero cuba
Varadero Beach: like something out of a travel magazine – photo courtesy of TripAdvisor

I had heard some good things about the beach here in Varadero and was not disappointed. Touristy? Yes. But the water was crystal clear and the sand some of the softest I’ve ever felt in my life.

I had a midnight dip with some friends under the full moon and could clearly see my feet at the bottom! It was utterly magical and the beach was perfect for chilling and getting a tan before my flight home.

I spent one day in Varadero out of my Cuba two week itinerary, but would recommend two if you’re a bit of a beach bum.

Aside from the beach, there isn’t all that much else to see in this resort destination but I heard there are some nice snorkelling spots and an interesting street market selling handmade souvenirs. So if like me, this is your last stop before heading back to Havana for your flight (day 14), it would be a great place to stock up on souvenirs before you go.

Reflections on My Cuba Two Week Itinerary

colourful colonial buildings in Havana, Cuba

Despite not initially being on my radar, I am so glad I made visiting Cuba a priority. The timeless cities brim with a vivacious atmosphere like nowhere else in the Caribbean and the crumbling colonial buildings and mansions completely captivate you with their decrepit beauty. 

Most unexpectedly for me, the locals were super friendly despite the language barrier; I felt like I was an adopted daughter by practically every Cuban family I stayed with!

If you can’t head to Cuba soon then it really should fast track to the top of your bucket list. As you’ve probably gathered, everything in Cuba moves slowly but there is no denying that Cuba will unfortunately start modernising at some point soon.

This Cuba two week itinerary is quite fast-paced and requires moving around every few days. I personally loved moving around and seeing such variety in Cuba – from the cities to the sleepy countryside. If you want to slow down a bit, I would recommend that you remove Cienfuegos from this Cuba two week itinerary.

Two weeks realistically only scratches the surface of this incredibly unique and vibrant country. If you ever have the opportunity to go for longer, I would highly recommend it!

Has this Cuba two week itinerary been useful? If yes – I’d love to hear about it!

Heading to Cuba soon? Don’t forget these essentials!

Flights: compare and search for the cheapest flights using Skyscanner

Accommodation: hotels to hostels, glamping to apartments, I always use

Tours: to find the best group tours and activities worldwide (with up to 20% off), use Viator

Visa: don’t forget to check the entry requirements for the passport you are travelling with

Inspiration: Lonely Planet’s guide to Cuba or to kick-start your next adventure, how about Lonely Planet’s Guide to the World?

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8 thoughts on “An Epic Cuba Two Week Backpacking Itinerary”

  1. It’s so nice to see someone shed light on places other than Havana! I had no idea there were so many beautiful towns and cities in Cuba. Thank you for telling us all about it in a great itinerary!

  2. Cuba is one of those places that’s always on my list but just keeps getting cast aside for other destinations. One day! Thanks for the tip about finding people to travel with if you’re a solo traveller – I wouldn’t have thought of that, but it makes a lot of sense re saving money.

  3. Cuba is truly a beautiful country with beautiful people. Would love to make it there one day. Great photos and thanks for sharing!

  4. Wow! What a detailed itinerary! Cuba is very high on my list, but I don’t know how soon I’ll be able to make it there. It must be a very fascinating country.

  5. I love this and the places look so beautiful!! I was supposed to go to Cuba this year but postponed it to next year. Saving this!

  6. I visited Cuba in 2018.. loved it! I spent some time in both Havana and Varadero.
    Havana was super interesting BUT we majorly got scammed by the tourist prices like you said! Also, we did go snorkelling in Varadero and it was amazing! As you said, the water is super clear. We also went swimming with the dolphins which was fun.


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