Cuba is the largest island in the Caribbean, and one of the world's few remaining communist states. This country has it all Caribbean beaches, history, colonial cities, US embargo! Who wouldn’t like travelling to Cuba for at least 2 weeks?
Nowadays you can virtually visit any country on this planet, there are obviously places which are easier to travel to than others, unfortunately, Cuba is under the difficult to travel in places. You can surely book your trip via a travel agent and perhaps visit Havana and one of the beach resorts hassle-free, but if you really want to immerse yourself in the country's culture his will be the last thing you'll think of.
Cuba is a resilient country, its communist government has survived more than 50 years of US sanctions and it also defied predictions that it would not survive the collapse of its one-time supporter, the Soviet Union. Fast-forward to the 21st century and many things have changed but there's always a constant, the name Castro, first, there was Fidel Castro who led the one-party state for almost 50 years after overthrowing Cuba's US-backed government in 1959. In February 2008, Fidel handed over power to his brother Raul Castro. Both men exercised control over virtually all aspects of Cuban life through the Communist Party and its affiliated mass organizations, the government bureaucracy and the state security apparatus. Exploiting the Cold War, Fidel Castro was for decades able to rely on strong Soviet backing, including annual subsidies worth $4-5 billion, and succeed in building reputable health and education systems. But, at least partly because of the US trade sanctions, he failed to diversify the economy.
But Cuba is a vast country and also rich in history. Centuries before the Castros, Cuba was already home to several groups of indigenous people. When the Spanish explorer, Christopher Columbus, set foot on the island in 1492 he claimed the land for the Spanish crown. The native population was quickly decimated by disease and forced labour, and Spain imported African slaves to grow sugar cane and tobacco.
Quick facts
Nowadays most Cubans earn very little money, with average salaries under $20 a month. However, healthcare and education are free, and many food staples are subsidized (which does not necessarily mean there is enough food for everyone).
Cuba is like a rough precious stone, you'll need to put in the effort if you want to experience its true beauty.
Day 1 - Old Havana & Havana Centre
In your first day in Havana (energy allowing) head to the historic centre. Stroll old Havana's charming streets and have your camera ready to take some great photos charming public squares, colonial churches and beautiful fortresses built by the Spanish. I'd personally recommend that when you start feeling hungry/thirsty you leave Bodeguita del Medio and Floridita (two of the most famous places in Havana where Hemingway used to hang out) for another day, instead have some food at Lamparilla Tapas & Cervezas and for drinks head to El Patchanka, two independently owned places (I can think at least two bearded cigar-smoking guerrilleros that would disapprove of this if they were alive). Havana is a very safe city for tourists but as in all places stick to well-lit streets and don't flash your valuables. Also, the La Coubre train station's area feels a bit rough around the edges so avoid it if you can at night.
Day 2 - Malecón, Miramar & Vedado
Start your day early with a cheap, BUT DELICIOUS sandwich and a freshly squeezed juice at Sandwichería La Bien Paga. Following this head to the Vedado neighbourhood where you'll be able to visit amongst other sights the Revolution Square, Chinatown and if you have time the Colon Cemetery. From here is on to the malecon (a promenade spanning 8 km along Havana's picturesque seaside). Many tourists will hire a (very expensive) vintage car taxi for about one hour to drive them around Havana and this will always include driving along the malecon, but you'll enjoy it much more if you just walk its length. At the very end of the malecon you'll come across the perfect place for a cold beer after a long day of sightseeing at the Torreon dela Chorrera which is a stone fortification, completed in 1646 right in the sea, SALUD!
Day 3 - From La Havana To Viñales
The best way for you to get to Viñales is by bus. Consider getting your Via Azul Bus tickets well in advance as they tend to sell out (even though this is Cuba you can book tickets in advance online). From Havana there are two buses a day to travel to Viñales. Company “Viazul” offers two buses a day from the main station. The first one is in the morning and the second is in the afternoon. The trip is 3 hours and 40 minutes long if the bus makes a halfway stop in Las Terrazas, and 2 hours if it doesn't. Once in Viñales, the whole valley is a national park with incredible limestone rock formations, traditional farms and villages where tobacco is grown. Spen your first day relaxing in Viñales town and perhaps at night head to the small town's main square where almost every evening there is salsa and fairly priced rum, beers and the quintessential mojitos.
Day 4: Viñales
In the morning, after your breakfast, it's now time to explore the valley either on foot, by bike or if you're into it, by riding on the back of a horse. There are plenty of people offering tours in the town so just shop around for the best deal or if staying at a casa particular chances are they will know someone. Most tours will take you to one of the tobacco farms where you can witness firsthand how they make the famous Cuban cigars and even try some.
Day 5: Viñales To Cay Jutías & Back
After 2 nights in Viñales, it is now time to leave the horseriding farmers behind for some hours and head to the beach, (if you wish, on the way, you can visit the Cueva del Indio - a massive cave system). Your beach paradise is called Cayo Jutias still somewhat untouched by mass tourism. This is easily done as a day trip from Viñales. The best way to get here is by taxi but you'll have to negotiate the price, once more, your hosts, if you're staying in a casa particular, will be able to get you a good deal.
Day 6: Viñales To Cienfuegos
After spending a couple of days in 'Cuban Texas' it's time to pack some sandwiches and brave the somewhat long bus journey to get to Cienfuegos (roughly 9 hours). There isn't much you can do on this day as most of it will be spent on a bus, however, this will also be an excellent opportunity to see the island nation's diverse landscape.
This would also be the ideal time to perhaps play some board games. One of my favourite is Hive.
Day 7: Cienfuegos
Cienfuegos attractions are all within walking distance from each other. You'll probably want to check Jose Martí Park, the Paseo del Prado, El Palacio del Valle and Punta Gorda (which you should really not miss as from here you can enjoy the beautiful sunset.
Day 8: Cienfuegos To Trinidad
The trip to Trinidad is a walk in the park when compared to the trip from Vinales to Cienfuegos, after less than 2 hours on the bus you'll have reached your destination. Now Trinidad is, in my opinion, the nicest of all Cuban towns. It's not too big, not too small. It feels safe and it's not as rundown as for instance Havana. Trinidad could even be called one of those cliches, the pearl of Cuba, and truth be told that would be no lie. To one side you have this amazing mountainous range covered in thick jungle and to the other the white sand beaches and turquoise waters of the Caribbean sea.
Spend your first day in our around the main square listening to salsa, drinking mojitos or canchanchara (a traditional drink from this region) and at nightfall go up to one of the many rooftops to enjoy a SUPERB sunset.
Day 9: Trinidad
On your second day explore the historic centre and don't feel afraid to check every nook and cranny of this cute little town. After you feel you had your fair share of exploring stop for some food at one of the coolest bars in the whole of Trinidad, El Mago - an artsy bar/restaurant with great music, great service, tasty food and spot-on cocktails. From here you could check a cool off the beaten track attraction, Trinidad's train station where you'll be able to see/photograph some cool old trains.
Day 10: Trinidad - Ancón Beaches
Today is the day when you'll finally hit the beach, and what a paradise this is. Playa Ancon is a picture-perfect beach with fine white sands and crystal clear waters. There are some new developments being built around the beach but they are still quite far, so apart from the state-owned soviet style hotel to the left of the beach you'll have a couple of kilometres of uninterrupted beach just for yourself (and probably some other tourists). The best way to get here is to get a taxi from Trinidad. If you ask them to come pick you up they will do so, otherwise, there will be taxis waiting to drive people back to the town.
Day 11: Trinidad To Topes De Colantes
You'll be asked time and time again two things in Trinidad, if you would like to tour the town in a horse cart or if you'd like to be taken on a tour to Topes De Colantes natural park. My advice is to politely ignore these people and instead book a tour to Topes De Colantes with a tour agency.
Topes De Colantes is an enjoyable one day tour (lunch included) where you'll be taught about the great biodiversity of this region, swim in waterfalls, visit coffee plantations and try some tropical fruits.
Day 12: Trinidad To Varadero
If you're like me you'll probably start second-guessing your decision to visit Varadero as soon as you get on the bus that will take you there. But let me tell you this, Varadero is actually OK. My fear were tourist hoards, overpriced food/drinks and the usual artificial atmosphere you get when you stay in a destination packed with resorts (obviously you may actually like his sort of holiday and I've got nothing against it). My worst fears didn't materialise. Sure, you have the resorts strip and you'll see your fare share of package holiday tourists but the beach is very long so rest assured you'll always find somewhere lay your towel. Then there's also Varadero town which is where locals live and where most cases particularly (Airbnb rooms) are located. There are also some decent food and beverage options around this area and some surprisingly cheap ones like Sabor Cubano where you can eat for less than 3$ USD.
Day 13: Varadero
The number one reason anyone visits Varadero is the beach. So today will be all about sunbathing and when you get too hot, going for a swim. Pack some food, bring some water, don't forget your sunglasses, sunscreen, beach towel, kindle and maybe one of those Cuban cigars, this is all you'll ever need to have a memorable day! Maybe also bring your mobile phone so you can take some selfies to send your friends back home and make them jealous of you.
Day 14: Day Trip To Matanzas
Matanzas is close to Varadero, so close you can just jump in a taxi to get there for not much. Most casual visitors to Cuba will no even consider stopping here. However, this is Cuba without the tourists so checking it out won't hurt. It may look a bit rundown but spend an afternoon exploring this city and I'm sure you'll see why I've included it on this 15 days itinerary of the island nation of Cuba. Matanzas is where rumba was born and you'll hear it everywhere. The city itself is nowadays reaffirming its attractiveness and some areas have had a facelift, the result is a small, yet pleasant historic centre that offers a nice getaway from Varadero.
Day 15: Varadero To La Havana + Flight Back Home
On your last day, if you have time before your flight back home, walk around your favourite area of Havana, maybe buy those souvenirs you still haven't bought, go check the malecon one last time, grab a mojito and say goodbye to the pearl of the Caribbean.
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