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How to Plan the Perfect Cuba Itinerary: A Guide To The Top Destinations (2024)

Vibrant, warm and addictive, Cuba is a unique and amazing place to explore. However, the largest island in the Caribbean is deceptively big, and picking the highlights can be tricky.

This post will help you plan the perfect Cuba itinerary, however much time you have to spend there. I’ve spent almost a month in Cuba and am excited to help you discover this fascinating country.

I’ll suggest a few different itineraries and routes, introduce you to some of my favourite places to visit in Cuba, and give you some additional hints and tips for getting the most out of your visit.

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.

Making friends with a hutia (Cuban tree rat)

1 Week Cuba Itinerary

If you only have one week, you’ll need to be even more selective.  Again, don’t try to cram too much in.

A possible 1 week Cuba itinerary might look something like this:

  • 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 Viñales OR take a day trip to Cayo Levisa
  • Day 7:  Travel:  Viñales > Havana
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.

I recommend starting with something similar to the 10-day itinerary above.

As you’ve got another four days to spare, you can also spend a couple of nights on Cayo Levisa, and maybe an extra night in Santa Clara and/or 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
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, book that instead.  However, these flights aren’t always available, so you might need to go via Santiago.

Typical scenery in rural Cuba with palm trees, green fields, and mountains
Typical scenery in rural Cuba

Best Places to Visit In Cuba

Here are some of my favourite places to visit in Cuba. It’s not an exhaustive list by any means, but it’s a good starting point for your trip.

1. Havana

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

Green vintage car in Havana
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 wafts 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

Pink convertible vintage car in old town havana with a cuban flag hanging from the wall of a building
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

The malecon in Havana with the waterfront sidewalk, colourful buildings, and the sea
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

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

Walking along the tree-lined pedestrian street Paseo del Prado in Havana
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

Che Guevara mural on the wall of a building in Plaza de la Revolución
Che Guevara overlooks Plaza de la Revolución

Plaza de la Revolución (Revolution Square) is a large square about 3.5 kilometres southwest 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.

2. 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.

Mountains and tobacco fields in Viñales
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.

Tobacco farmer leading a horse through a field in Viñales
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.

Cuban woman making a cigar by hand in Vinales
A delicious Cuban cigar being made by hand

3. 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.

Empty beach on Cayo Levisa with turquoise sea, blue sky, two sun loungers, and palm trees
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.

Beautiful unspoilt beach on Cayo Levisa with no people and amazing aquamarine sea
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 idyllic tropical paradise beaches (who isn’t?), check out this guide to Praia da Almada, Brazil.*

4. Trinidad

The beautiful town of Trinidad is probably my favourite place in Cuba.

Exploring the cobbled streets of Trinidad, Cuba, with colourful colonial buildings and a few people walking by
Exploring 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.

Oil paintings on canvasses displayed inside an artist's studio in Trinidad, Cuba
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.

Historic streets of Trinidad at dusk with streetlights casting an atmospheric glow and a yellow and white bell tower rising into the sky
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 was electric.  

By the end of the show, most of the audience was dancing.

Man and a woman dancing in front of a live Cuban band playing in Trinidad
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.

Man playing guitar and woman playing violin in a restaurant bar in Trinidad with an open door behind showing an old yellow building
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.

People dancing indoors in a building with blue walls and portraits of che guevara on the wall at a spontaneous dance party in Trinidad
Spontaneous dance party? Free rum? Yes, please!

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

5. 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.

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.

6. 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 the rooftops of Cienfuegos
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.

7. Santiago de Cuba

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

View over Santiago de Cuba and the surrounding mountains
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.

Typical street in Santiago de Cuba with old run down buildings
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.
  • Plaza de Marte: a central area, popular with the locals, with many shops, restaurants and bars.
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.

8. Baracoa

Near the southeastern 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.

View over the rooftops of Baracoa with the sea beyond
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.

Colourful buildings in Baracoa with the table-top El Yunque mountain in the distance
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.

Check out this post for some useful Spanish words and phrases!

Best Time To Visit Cuba

Cuba has a tropical maritime climate with distinct dry and wet seasons.

The best time to visit Cuba is generally during the dry season (December-April) when the weather is sunny and not too humid.  

The rainy season lasts from May until October, with the rains usually getting steadily heavier as the season goes on.  

I visited in May and it did rain most days, but rarely for more than an hour or two at a time, and usually only in the afternoon.

From August until October, there is a risk of hurricanes which can cause extensive flooding and disruption to travel.

Sunset colours over the sea in Cuba with the silhouette of a thatched beach shelter in the foreground
Ah Cuba, I miss you

If you’re interested in planning a self-drive Cuban road trip, The BeauTraveler has an excellent post on how to rent a car in Cuba.

FAQs About Visiting Cuba

Here are answers to a few frequently asked questions about planning a trip to Cuba.

Is 7 days enough to visit Cuba?

7 days is enough time to visit Cuba and experience a few of its key highlights. During this time, you can explore the vibrant streets of Havana, visit historic sites, relax on some beautiful beaches, and immerse yourself in the rich Cuban culture and music. However, the longer you can spend in the country, the better. There’s a lot to see!

Is Cuba safe to visit?

Cuba is a very safe country to visit with a welcoming and friendly atmosphere. However, like any travel destination, it’s wise to take standard precautions, such as safeguarding personal belongings and staying aware of your surroundings, especially in busy areas.

Do you need a visa to visit Cuba?

Most visitors need a visa to enter Cuba, often called a “tourist card”. The requirements can vary based on your country of origin, so it’s important to check the specific visa requirements for your nationality before travelling.

Can US citizens travel to Cuba?

U.S. citizens can travel to Cuba, but they must comply with certain regulations. While travel purely as tourists is not allowed, Americans can visit Cuba under specific authorized categories, like “Support for the Cuban People.” This involves engaging in activities that support local, non-government-owned businesses in Cuba.

Can I go to the USA if I have been to Cuba?

If you have visited Cuba on or after January 12, 2021, you will need to apply for a U.S. visa to enter the United States, as you won’t be eligible for the Visa Waiver Program (VWP) or the Electronic System for Travel Authorization (ESTA). This policy is in place because Cuba is (bizarrely) listed on the U.S. State Sponsors of Terrorism list, which affects ESTA eligibility.

Final Thoughts

Cuba offers an irresistible blend of history, culture, and adventure. From exploring Havana’s vibrant streets to relaxing on pristine beaches, there’s so much to see and do on this enchanting island.

It would be impossible to cover everything in one visit. You could spend months in Cuba and still not see everything.

Embrace the rhythm of the island and get ready for an unforgettable journey!

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