A Rough Guide to Two Weeks Backpacking Captivating Cuba

Colourful Havana Street Scene


Cuba has recently been at the centre of attention thanks to its turbulent political relationship with the US. However it was shortly after President Obama lifted the United State's 50 year old embargo, that Cuba really came to the forefront of many peoples' minds as a travel destination. In 2016, tourists all over the world frantically scrambled to catch a glimpse of ‘authentic’ Cuban life before modernity and Americanisation seeped into the cracks of the dilapidated buildings, shamelessly turning them into McDonald's and chain grocery stores. 

When visiting Cuba’s neighbour, Jamaica, in January 2016 people were regularly asking me whether I had been, or was going to Cuba as part of my trip. I was not. I actually hadn’t even considered Cuba before. Nonetheless, I was advised to go NOW, this second, right away, ASAP. So just like everyone else, I totally freaked out and booked a flight as soon as physically possible.

Despite being a picturesque 50's time capsule, I soon discovered that 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, some times the most rewarding and fun trips are the ones that not only challenge you, but also broaden your horizons - this being just one reason why I think Cuba is one of the most unique places in the world.

The colourful cobbled streets of Trinidad

The colourful cobbled streets of Trinidad



Planning your trip

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 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. This was partly because my full-time job at the time was so demanding so I couldn't do much research. I also 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. For example, when I arrived at one of the handful of hostels in Havana, I soon met two lovely French girls and tagged along with them as I was uncommited. 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. 

Vintage cars in Havana, Cuba

Here are some other important points that are worth knowing before you touch down 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 convertable 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 but 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.

  • 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/fanny pack 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. Aside from this, I was offered drugs once but they were pleasant when I said a polite 'no thank you' and let me get on my way. Generally I found the Cuban people really inquisitive and very kind and I didn't feel threatened once.

Me (questionably rocking a bumbag) with the lovely Frenchies, Margaux and Juliette in Cienfuegos

Me (questionably rocking a bumbag) with the lovely Frenchies, Margaux and Juliette in Cienfuegos



The Itinerary

Below is an outline of places I visited on my trip. Again, this is only a guide. Instead follow your own flow when you are out there: 


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


Here is what I got up to in each place as a guide for your own trip:


(Day 1,2,3)

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 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.

Vintage convertible cars lining the Malecon in Havana
Lighthouse and Fort Castillo Del Morro in Havana
Gazing over to Havana from the Fort



(Day 4)

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.

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:

  • 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 apparently 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.

Jungle of the Las Terrazas National Park

Jungle of the Las Terrazas National Park

The amazing view from the Che Monument - ha!

The amazing view from the Che Monument - ha!

Our ride from Havana we flagged down in the street and shared with other backpackers

Our ride from Havana we flagged down in the street and shared with other backpackers




(Day 5, 6, 7)

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.  The atmosphere here 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:

  • 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 is only a 10 minute walk from the town.

sunset skies over fields in Vinales, Cuba

sunset skies over fields in Vinales, Cuba

Pristine white sand and aqua water at Cayo Jutias Beach
Horse riding tour through fields and tobacco plantations



(Day 8)

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 and although I thought it pleasant enough, I'd recommend going for just one day as I didn’t feel there was actually all that much to do there other than the following:

  • 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.

Sightseeing in Cienfuegos
View over Cienfuegos from the Mirador Jose Ferrer viewpoint
Playa Rancho Luna Beach



(Day 9, 10, 11)

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:

  • 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. 

Local children playing football on the cobbled plaza of Trinidad
Tour to the Topes De Colliantes National Park
View over the mountains from a mirador in Trinidad



(Day 12, 13)

I had heard some good things about the beach here 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 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. 

The aqua water and white sand of Varadero Beach - photo courtesy of TripAdvisor

The aqua water and white sand of Varadero Beach - photo courtesy of TripAdvisor



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 is an utterly unique destination that will unfortunately start modernising at some point soon. 

A street scene with a bicycle tuk-tuk in Trinidad
crumbling colonial mansions in Havana
The pedestrian strip with artists and souvenir sales, Habana

Thanks for reading and feel free to leave any comments below!