Cuba Itinerary: Ultimate Guide To The Top Destinations

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Cuba is one of the most incredible places in the world.  Vibrant, warm and addictive, it’s an amazing place to explore.  However, the largest island in the Caribbean is deceptively big, and picking the highlights can be tricky.  The perfect Cuba itinerary depends on how much time you have.

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Typical scenery in rural Cuba

There’s so much to see and experience here, it would be impossible to cover everything in one visit.  You could spend months in Cuba and still not see everything.

In this post, I’ve set out a few suggested Cuba itineraries, and a brief flavour of what you can expect to find in each place.  I hope it inspires you to plan a visit!

Best Destinations In Cuba

These are some of the highlights, which can be included in various combinations when planning your Cuba itinerary.

Havana

One of the most iconic cities in the world, there’s nowhere quite like Havana.

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A Cuban icon

Wandering the streets of the Cuban capital, you’ll feel like you’ve stepped into a movie set.  And a really cool one at that.

Colourfully painted, elaborate, crumbling buildings.  Shiny, classic vintage cars.  Irresistible music wafting through the warm, tropical air.  Everywhere you look, there’s no mistaking you’re in Havana.

Things to do in Havana

Every Cuba itinerary should include at least a couple of days in Havana.  However, the longer you can spend here, the more you’ll get a sense of its unique feel and rhythm.

Unless you’re really pressed for time, I’d recommend spending at least 3 days in Havana.  There’s a lot to see and experience here.

Habana Vieja

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There's nowhere quite like Havana

Habana Vieja (Old Havana) is the historical centre of the Cuban capital.  Despite being one of the most recognisable tourist locations in the country, it still feels very authentic.  People live and work here, surrounded by the most amazing faded grandeur.

Old Havana is full of crumbling colonial architecture, colourful buildings, narrow side streets, attractive little squares, tiny shops and galleries.  Music drifts down from many of the balconied apartments, and cigar smoke lingers in the air.

The best way to experience Habana Vieja is to get lost in the backstreets, exploring wherever the fancy takes you.  It’s a magical place.

The Malecon

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Late afternoon on the Malecon

The Malecon is Havana’s iconic waterfront, stretching from Centro Habana to the upmarket residential neighbourhood of Vedado.

It’s a perfect place for a stroll, stopping off at some of the quirky little cafes and bars along the way.

You could also take a cruise along the Malecon in one of Havana’s amazing 1950s classic cars, which serve as taxis throughout the country.

El Capitolio

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El Capitolio

The National Capitol Building – El Capitolio, to the locals – is one of Havana’s most photographed buildings.

Before the Cuban Revolution of 1959, the building housed the country’s Congress.  Abandoned for decades, today it is being restored to its former glory.  Once it’s finished, the government has stated that it intends to move the National Assembly back into the building.

You can take a tour of the beautifully ornate interior, assuming it’s not closed (which, frequently, it is… this is Cuba).

Paseo del Prado

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Take a leisurely stroll down Paseo del Prado

Paseo del Prado is a wide, leafy pedestrianised street that runs between El Capitolio and the Malecon.

It’s a popular place where many locals, young and old, like to meet.  Children play football and other games, couples and friends take strolls or sit under the trees and chat.  Sometimes there are exhibitions and art sales here.

Paseo del Prado is a perfect place to wander, or just hang out, as the locals do.  Take a walk, sit, and watch the world go by.

Plaza de la Revolución

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Che Guevara overlooks Plaza de la Revolución

Plaza de la Revolución (Revolution Square) is a large square about 3.5 kilometres south-west of El Capitolio.  Surrounded by austere, grey buildings, this is the political administrative centre of Cuba.

The plaza has hosted many political rallies, and Fidel Castro made countless addresses from here.  Several important governmental buildings are located around the square, including the Palace of the Revolution – the current house of the Cuban government and Communist Party.

A large, iconic steel mural of Che Guevara is located on the side of the Ministry of the Interior building.

Viñales

The Valle de Viñales (Viñales valley), in the western region of Pinar del Río (about 3 hours from Havana), is famous for its tobacco plantations.  Some of the best quality Cuban cigars are made here.

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Mountains and tobacco fields in Viñales

Valle de Viñales is green and lush, with unusual limestone rock formations (called “mogotes“), which are riddled with elaborate caves.  Some of these contain underground lakes, where you can swim, in the pitch dark (very disorienting but quite cool!).

The small town of Viñales itself, although fairly touristy, is a good place to get a sense of life in rural Cuba.  The majority of people here are farmers, who work in the tobacco and coffee plantations.  It’s a great place to relax, surrounded by the beautiful Cuban countryside.

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Tobacco farmer in Viñales

The valley is easily explorable on foot, and I’d recommend spending at least a day doing just that.  It’s very tranquil, you’ll see lots of wildlife and some beautiful scenery.

You can also take a tour of the area, either walking or on horseback.  These tours typically include a visit to one of the tobacco plantations, where you will be shown how the region’s world-famous cigars are produced.  Some tours also include a visit to the local coffee plantations and/or one of the many large caves.  Tours are easily arranged on the day through your casa particular – no need to book in advance.

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A delicious Cuban cigar being made by hand

Cayo Levisa

Forget Varadero (the popular resort town in the north of Cuba).  Okay, to be fair, Varadero’s probably great if you like touristy all-inclusive hotels with spa complexes and golf courses, full of European and North American tourists.  But that’s not why you want to come to Cuba, right?  Good. 

Cayo Levisa, on the other hand, has equally stunning white sand beaches and clear, turquoise waters, but with a fraction of the number of tourists.  So much better.

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Cayo Levisa is untouched, unspoilt, and picture-perfect

Much of the southern half of the island is a mangrove forest.  The northern shore is one long (3 kilometre) stretch of perfect, mostly untouched, beach.  There are several dive sites in the surrounding coral reefs, and you can also snorkel from the beach.

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Tropical paradise - minus the crowds

Cayo Levisa is accessible via a tiny ferry, which runs twice daily from Palma Rubia on the mainland.  You could easily visit the island as a day trip (Palma Rubia is about an hour’s drive north from Viñales).

For those with more time, there is one small hotel on the island, with several bungalows and huts next to the beach.  The hotel is fairly basic, but perfectly fine.  Once the day trippers have caught the boat back to the mainland, you can have the island virtually to yourself.

It’s your own beautiful slice of tropical paradise.  I could easily spend weeks here.

*If you’re into stunning tropical paradise beaches (who isn’t?), check out this guide to Praia da Almada, Brazil.*

Trinidad

The beautiful town of Trinidad should definitely feature on your Cuba itinerary.

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Exploring the beautiful old town of Trinidad

Trinidad’s picturesque old town is full of colourful colonial buildings and winding cobbled streets.  It’s the perfect place to get lost, chatting to the friendly locals, and soaking up the atmosphere.

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Amazing artwork in Trinidad

Walking past open doors, you’ll see incredible artists painting on canvas.  People might smile and wave to you through their windows.  Old-timers sit on doorsteps smoking cigars and chatting with friends.  Music drifts through the air wherever you go.

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Dusk falls over atmospheric Trinidad

Trinidad has some great nightlife.  Casa de la Musica, near the Plaza Mayor, hosts regular live musical performances.  I heard a fantastic band play here, they were equally as good as the famous Buena Vista Social Club.  The outdoor square was packed, and the atmosphere electric.  By the end of the show, most of the audience was dancing.

Incredible music and dancing at Casa de la Musica

There are many great bars and restaurants here too.  Taberna La Botija is a particularly good one, and has an amazing house band.  Try their Canchánchara – a delicious cocktail made with sugar cane spirit, honey, and lime.

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Great music at Taberna La Botija - one of the best bars in Trinidad

Salsa is HUGE in Trinidad.  You see people dancing everywhere – in their homes, in the bars, and in the streets.  It’s amazing.  

Passing the Club Amigos del Danzon one evening, I was beckoned in by a friendly local who spoke no word of English but who gave me a (very large) glass of rum, saying “dance and be happy!“.  A totally spontaneous and great evening.

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Spontaneous dance party? Free rum? Yes please!

Check out this excellent guide to Trinidad, written by Yvonne over on Willas Cherry Bomb.  (The post is written in German, but there’s a handy translate bottom at the top right of the page.)

Santa Clara

The large town of Santa Clara, in the centre of Cuba, was the scene of a pivotal moment in modern history.  It was here that the final battle of the Cuban Revolution was fought in 1958.  

Today, it’s known as the “City of Che”, after the man who commanded the revolutionaries who won the battle.

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Ever forward to victory! Che looks out over Santa Clara

You can visit the Che Guevara Mausoleum, which houses the remains of the famous revolutionary.  There’s also a small museum in town, and countless other sites dedicated to the man and his legacy.

Cienfuegos

Cienfuegos is an attractive city built on a bay, on Cuba’s southern coast.

There aren’t many “sights” here per se, but it’s a pleasant place with colourful buildings and French-inspired architecture.

Sunset over Cienfuegos

Take a wander through the backstreets near the main square, explore the Parque José Martí and Paseo del Prado (the little cousin of the one in Havana).  At the end of the day, enjoy a sundowner from the rooftop at Bar Terrazas, looking out over the city.

Santiago de Cuba

The gateway to the eastern half of the island, Santiago de Cuba feels very different to the country’s western side.  

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View over Santiago de Cuba and the surrounding mountains

Partly this is due to geography.  Cuba’s second-largest city is closer to Haiti than Havana, and is hotter and more humid than the western regions.  Santiago also has a rich Afro-Cuban heritage, and is home to some of the best musicians in Cuba.

Every July, the city hosts Cuba’s most vibrant carnival.  This two week-long party is an explosion of energy, music, street parades, colourful costumes, singing and dancing.

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Typical street in Santiago

The city centre is fairly compact, and best explored on foot.

Highlights include Parque Cespedes – the central plaza where Fidel Castro declared victory in the Cuban Revolution, Avenida Victoria de Garzón – where you’ll find some of the best street food in the country, and Plaza de Marte – a central area, popular with the locals, with many shops, restaurants and bars.

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Musicians are everywhere in Santiago de Cuba

Santiago de Cuba is world-famous for its incredible music scene, and Casa de la Trova is the city’s oldest – and best loved – live music venue.  This amazing bar was the birthplace of son Cubano, the iconic genre (made famous by Buena Vista Social Club) that is often described as “a love affair between the African drum and the Spanish guitar“.  Here you can watch some of the best live music in Cuba.

Baracoa

Near the south-eastern tip of Cuba lies one of the island’s most remote, and idyllic, towns.  Surrounded by forested mountains on one side and the beautiful Bay of Honey on the other, Baracoa enjoys a stunning location.

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Baracoa and the Bay of Honey

It was here where Christopher Columbus first landed on the island.  Today, the town is fairly quiet, with a laidback lifestyle that’s more than a little infectious.  If you were looking for a remote, peaceful little town to take a salsa or Spanish course, write a book, or just unwind, Baracoa would be a pretty ideal place to choose.

Baracoa is known for its chocolate and coconuts.  Both are excellent in quality and feature heavily in the region’s unique cuisine.

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The table-top El Yunque mountain stands over Baracoa

A popular day trip from Baracoa is to climb El Yunque, a flat-topped table mountain which overlooks the town.  

There are also several stunning beaches and attractive fishing villages within easy cycling distance from Baracoa (ask your casa particular host about bike hire).  Playa Cajuajo is a good one, but you can basically just cycle along the coast in either direction until you reach a secluded spot.

10 Day Cuba Itinerary

Cuba is larger than many people realise.  The island is about 1,250 km long, with an area almost the size of England.  Many roads are in poor shape, and it can take a fair amount of time to get from place to place.

I’d strongly suggest not trying to cram too many destinations into a 10 day Cuba itinerary.  Rushing from place to place, you will miss a lot of what makes Cuba so special.

In 10 days, you should be able to see many of the highlights in western/central Cuba.  Assuming you are flying into and out of Havana, I’d suggest the following itinerary:

  • Day 1:  Arrive in Havana
  • Day 2:  Havana
  • Day 3:  Havana
  • Day 4:  Travel:  Havana > Viñales
  • Day 5:  Viñales
  • Day 6:  EITHER enjoy a second full day in Viñales, OR take a day trip to Cayo Levisa
  • Day 7:  Travel:  Viñales > Trinidad
  • Day 8:  Trinidad
  • Day 9:  EITHER enjoy a second full day in Trinidad, OR travel > Santa Clara OR Cienfuegos
  • Day 10:  Travel:  Trinidad (/Santa Clara /Cienfuegos) > Havana

An alternative itinerary for those who would prefer to visit the eastern half of the country might be:

  • Day 1:  Arrive in Havana
  • Day 2:  Havana
  • Day 3:  Havana
  • Day 4:  Fly:  Havana > Santiago de Cuba
  • Day 5:  Santiago de Cuba
  • Day 6:  Santiago de Cuba
  • Day 7:  Travel:  Santiago > Baracoa
  • Day 8:  Baracoa
  • Day 9:  Baracoa
  • Day 10:  Travel:  Baracoa > (taxi/bus) > Santiago > (fly) > Havana *

* If you can find a direct flight from Baracoa to Havana, try and book that instead.  However, these flights aren’t always available, so you might need to go via Santiago.

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Making friends with a hutia (Cuban tree rat)

1 Week Cuba Itinerary

Those with only one week to spare will need to be more selective.  Again, don’t try to cram too much in.

A possible 1 week Cuba itinerary might look something like:

  • Day 1:  Arrive in Havana
  • Day 2:  Havana
  • Day 3:  Havana
  • Day 4:  Travel:  Havana > Viñales
  • Day 5:  Viñales
  • Day 6:  EITHER enjoy a second day in ViñalesOR take a day trip to Cayo Levisa
  • Day 7:  Travel:  Viñales > Havana
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Super cool kid says you need more than one week in Cuba

2 Week Cuba Itinerary

You can see a decent amount of Cuba in two weeks.  However, I’d still suggest either sticking to the western/central or eastern halves of the island.  Trying to do both in two weeks would be too rushed in my opinion.

My recommended 2 week Cuba itinerary is very similar to the 10 day one, above.  As you’ve got another four days to spare, you can also spend a couple of nights on Cayo Levisa, and see a bit of both Santa Clara and Cienfuegos.  

Of course, if you’d prefer more time on the beach, feel free to play around with the below to suit your preferences:

  • Day 1:  Arrive in Havana
  • Day 2:  Havana
  • Day 3:  Havana
  • Day 4:  Travel:  Havana > Viñales
  • Day 5:  Viñales
  • Day 6:  Viñales
  • Day 7:  Travel:  Viñales > Cayo Levisa
  • Day 8:  Cayo Levisa
  • Day 9:  Travel:  Cayo Levisa > Trinidad
  • Day 10:  Trinidad
  • Day 11:  Trinidad
  • Day 12:  Travel:  Trinidad > Santa Clara
  • Day 13:  Travel:  Santa Clara > Cienfuegos
  • Day 14:  Travel:  Cienfuegos > Havana
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Time for some proper exploring

3 Week Cuba Itinerary

If you are lucky enough to be in Cuba for 3 weeks (or more), you’re in for a treat!  

With this amount of time, you’ll be able to explore both the western and eastern halves of the island.  (Or just spend even longer in each place, if you prefer.)

My suggested 3 week Cuba itinerary would be as follows:

  • Day 1:  Arrive in Havana
  • Day 2:  Havana
  • Day 3:  Havana
  • Day 4:  Travel:  Havana > Viñales
  • Day 5:  Viñales
  • Day 6:  Viñales
  • Day 7:  Travel:  Viñales > Cayo Levisa
  • Day 8:  Cayo Levisa
  • Day 9:  Travel:  Cayo Levisa > Trinidad
  • Day 10:  Trinidad
  • Day 11:  Trinidad
  • Day 12:  Travel:  Trinidad > Santa Clara
  • Day 13:  Travel:  Santa Clara > Cienfuegos
  • Day 14:  Travel: Cienfuegos > Havana
  • Day 15:  Fly:  Havana > Santiago de Cuba
  • Day 16:  Santiago de Cuba
  • Day 17:  Santiago de Cuba
  • Day 18:  Travel:  Santiago > Baracoa
  • Day 19:  Baracoa
  • Day 20:  Baracoa
  • Day 21:  Travel:  Baracoa > (taxi/bus) > Santiago > (fly) > Havana *

* If you can find a direct flight from Baracoa to Havana, try and book that instead.  However, these flights aren’t always available, so you might need to go via Santiago.

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Ah Cuba, I miss you

COMING SOON:  Practical tips & info for visiting Cuba.

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