YPT Tours to Cuba

Sun, sand, sea, cocktails, and communism. It is an exciting time for Cuba tours, as it is just ushering in a post-Castro era. Our Cuba tours will show you the island in all its glory, the YPT way. 

Explore the best of Cuba with us, get to know the historic centre of Havana as well as our secret communist locations in the outskirts – the first permanent monument to Lenin, dedicated just four days after his death, and the bunker where the nuclear warheads were kept during the Cuban Missile Crisis, where World War 3 could have kicked off.

On our Cuba tours, can also visit the colonial towns of Trinidad and Cienfuegos, try local rum and cigars, drive along the scenic Bay of Pigs while learning about its fascinating history and snorkel in the turquoise Caribbean waters. 

Experience Cuban hospitality, discover the natural beauty of Viñales, and even dance all night in a disco located inside a cave. Choosing a YPT Cuba Tour is the best way to see all that Cuba has to offer.

Group Tours to Cuba

We currently run Cuba Tours twice per year. In May, we join in the Cuban celebrations of May International Workers’ Day, by far the biggest celebration in the country. This is something like a Soviet-era parade with a good dose of Latin American carnival spirit!

Cuba May Day Revolutionary Tour – April 25th – May 2nd / 4th 2025 – $595 / $945 / $1295

Cuba May Day & Colombia Combo Tour – April 25th – May 13th 2025 – $2495

Also we run the same itinerary in the winter, for New Year’s Eve, but instead of celebrating May Day, you can start the year with a mojito in your hand while you explore the best of the Pearl of the Antilles.

Cuba New Year: Che Guevara and Missile Base Tour – December 26th, 2024-January 2nd/4th, 2025 – $895 / $1195

Independent Tours to Cuba

Young Pioneer Tours has been working (and living!) for more than 10 years in Cuba. As such we know the country like the back of our hands and can arrange independent and bespoke Cuba tours, no matter what you’re looking for: budget tours to experience the essentials, political tours, relaxing trips on a Caribbean beach, etc. Prices depend on the number of people and what level of accommodation you require.

Below is an example of an independent Cuba Tour.

Example of a Cuba Itinerary (10 days)

Day 1 – Havana, Cuba

• Arrive at your own leisure and transfer from José Martí International Airport to the Vedado part of Havana.
• An official taxi from the airport is CUC$25. Alternatively, YPT can arrange meet-and-greet pickup in an old 1950s American car for $50, or arrive in real style in a classic convertible for $95.
• On arrival at the casa, your guide will show you to your homestay (all have A/C and hot shower), where you will be free to relax or meet up with other group members to drink some cool beers.

• We head for dinner at Cafe Laurent, one of the oldest, and we feel best private restaurants, with a range of options to fit all budgets
• We finish the night in classic Cuban style by grabbing a carton (or two) of rum, and going to people watch on the Malecón – Havana’s famous seawall, known as the “sofa of the city”
• Overnight in Vedado

Day 2– Havana – Cienfuegos

• Breakfast at hotel and depart for the historic city of Cienfuegos, a UNESCO world heritage – 5-hour drive via Bay of Pigs
• On the way to Cienfuegos we travel along the flat central plain of Cuba where there are lots of citrus plantations. We turn off the main highway and shortly after the scenery changes to a densely vegetated swamp where the natural fauna includes boa snakes and crocodiles. We can visit a crocodile farm here at Boca de Guamá.
• Once reaching the Caribbean coast we travel along the picturesque Bay of Pigs past the site where the landing of counter-revolutionary exile militia occurred in 1961.

• Today we visit the museum here that recounts the events of this conflict which resulted in the first defeat of a US-backed takeover in Latin America. There are some beautiful places to stop for a swim along the way including a sink hole which resembles a huge natural tropical fish tank, so make sure to pack your swim wear. SCUBA diving and snorkelling are optional activities here. Cubans are known to be very proud people, and the citizens of Cienfuegos call their town La Perla del Sur (the pearl of the south). Founded by the French, Cienfuegos’ appeal lies partly in the European flavour of its colonial hub, with a wide Parisian-style boulevard and elegant colonnades, and there is an ambiance to inspire Cuba’s most celebrated Son singer to write the words “Cienfuegos is the city I like best”.
• After checking-in with your host family, you will have a short time to walk around the city and take in the atmosphere. You may go with your guide or explore on your own.
• Dinner at a local paladar private restaurant
• Explore the nightlife of Cienfuegos
• Overnight in Cienfuegos

Day 3 – Cienfuegos – Trinidad

• Breakfast and begin a walking tour around Cienfuegos with the first stop being the historic Teatro Tomás Terry.
• Depart for Trinidad, stopping en route at Palacio de Valle – the outlandish house of an eccentric millionaire (1.5 hours drive)

• Lunch on arrival in Trinidad
• We head off on our walking tour of Trinidad.
• La Villa de la Santisima Trinidad was founded by Velazsquez in 1514 and the defender of indigenous rights in the Americas, Fray Bartolome de Las Casas, attended over the settlement’s first mass. The future conqueror of Mexico, Hernan Cortes, recruited sailors here for his future expedition into that land. It is a charming, small town with the green mountains in the background, and the turquoise waters and pure white sand beaches of the Caribbean Sea just a short distance away. The town was fairly inactive until the 1800s, when French refugees fleeing a slave revolt in Haiti landed here en masse and brought with them sugar cane cultivation. The new residents settled and farmed in the Valle de Los Ingenios, just northeast of the town. Vast wealth flowed into the local economy from sugar cane cultivation and the area produced one third of the country’s sugar at one point. The sugar boom was terminated by the two wars of independence, but the wealth generated by the industry remains visible in the town’s once grand mansions, colourful public buildings, wrought iron grillwork and cobble-stoned streets. The town and area also saw a lot of action during and following the triumph of the Revolution, as gangs of counter revolutionaries hid out and struck from the safety of the mountains.
• Visit to The Museo Nacional de la Lucha Contra los Bandidos which tells the struggles of town’s history. The best part is the view from the tower!
• Dinner in a local top private restaurant.
• The nightlife in Trinidad is probably the most accessible and intense in all of Cuba, with numerous live music venues and many dance performances every day of the week, all amongst the enchanting setting of old colonial buildings and cobblestone streets.
• It’s optional but we very strongly recommend a visit to the unique and (in)famous Disco Ayala, a nightclub in an underground cavern!
• Overnight in homestay

Day 4  – Trinidad

• Breakfast and a day of choose your own adventure.
• Option 1: take a trip to the beautiful Valle de los Ingenios in the morning by classic train if it’s operating for $10
• Option 2: include a visit to the beach (Playa Ancón) and relax in the sun

• Both of the above options can include a salsa dancing lesson for $25 or horse riding in the afternoon for $20
• Dinner, drinks and overnight at our homestay

Day 5 – Trinidad – Santa Clara

• Breakfast and being our journey to the city of Santa Clara, which was a key city in the triumph of the Revolution.
• Depending on road conditions we can take a number of different routes around or through the Sierra del Escambray making a few stops along the way.

• Upon entering Santa Clara there is a huge statue of Ernesto Ché Guevara, beneath which is the mausoleum where he is buried. We visit the museum here that is dedicated to his life.
• Take a walking tour of Santa Clara where we come across significant sites such as the armoured train derailed by Che and his troops, in the final battle of the Cuban revolution.
• Dinner and optional evening of local music.
• Overnight in Santa Clara

Day 6 – Santa Clara – Havana: New Year’s Eve!

• We head back to Havana in the morning, stopping at open air October Crisis Museum overlooking Havana bay, featuring Soviet nuclear missiles (thankfully now inert!) of the period in 1962 when the world came closer than ever to the brink of nuclear war.

• Lunch in city
• Visiting San Carlos de la Cabaña fortress where Che had his office.
• Visit to the Havana Club Museum of Rum! Of course, free samples are available.
• Head out for a grand feast for dinner to farewell the old year and prepare for the new!
• Our YPT guide knows the bar streets of Havana better than the back of his hand! Expect the most atmospheric parties, dancing locals, and amazing cocktails!
• Overnight in homestay

Day 7– Havana: New Year’s Day

• Breakfast at homestay and begin our city tour of Old Havana, encompassing the Plaza de las Armas, complete with a statue of Manuel de Cespedes, one of the leaders of the independence movement. We pass the spot where the city of Havana was founded almost 500 years ago. We explore the open-air exhibit of the Museo de la Revolución to see the yacht Granma and learn about its importance in Cuban history.

• Afternoon free time or rest for those weary. Our guide can make recommendations to you particular interests.
• Dinner at our favourite secret private restaurant
• Optional but very strongly recommended visit to Fábrica de Arte Cubano (FAC – Cuban Art Factory, $2). This is one of the coolest art and night venues in the world right now.
• Drinks, Havana style, on the Malecón
• Overnight in homestay

Day 8 – Havana – Viñales

• Depart at 11.00am for Viñales, depending on Cuban bureaucracy! Our first stop is Lenin Hill, which is where the first ever statue of Lenin was erected following his death, this is very derelict and not at all touristy!
• Lunch at a Cuban style street restaurant
• We now visit the incredibly secret bunker where the Soviet Union stored the nuclear weapons that precipitated the Cuban Missile Crisis. This site is of extreme historical significance and was only recently discovered. This is not on the tourist trail!
• We now visit the former Soviet embassy, a huge example of socialist architecture, as well as some other Soviet-era tower blocks for some great fusion photos of Havana’s rich history

• We now take the 2–3-hour scenic drive to Viñales. On arrival, we check into our casa before heading out for dinner and drinks in this formerly sleepy town that whilst still relaxing now has a bustling nightlife.
• Overnight in Viñales

Day 9– Viñales

• In the morning, we head to the prehistoric wall for some amusing photos before heading over to a tobacco farm for a chance to see the process of cigar making, as well as have a try of the produce
• Another great reason to come to this farm is for the stunning views of the surrounding rolling hills that you get from here

• Lunch at farm accompanied by great views
• Viñales is famous for its stunning caves, with a number being big tourist attractions, we avoid them like the plague grab our local guide and head to a cave that is (currently) relatively unknown. It takes an hour hike, and then heading through the cave network with lights before we hit the swimming part of the adventure. Truly stunning, so don’t forget the go-pro!
• We head back to the casa for a shower before heading out to a great vantage point to enjoy our last sunset with a cocktail as a group
• We finish our last night in Viñales with an authentic home cooked Cuban meal at our casa.
• Drinks and conversation in the rocking chairs on the patio to end our last evening
• Overnight

Day 10  – Viñales – Havana

• Breakfast and begin our journey back to Havana – 3-hour drive
• Tour concludes! YPT can arrange a private taxi to the airport for you if you wish, or we can help with accommodation if you want to stay longer.

Bespoke Cuba Tours 

We do not list all of our bespoke Cuba tour itineraries, but we can offer some examples, such as the following:

Santiago and Sierra Maestra Tour

Explore the whole island and visit some of the key sites of the Cuban revolution, visit Fidel’s grave and get to know the second biggest city in Cuba.

Hikes and Birdwatching in Viñales

If nature is what you like, stay in one of the most beautiful regions in Cuba, climb its prehistoric mountains, the mogotes, and witness the diverse endemic fauna and flora.

Beach relaxation tour

Complete your trip in Cuba by spending some days relaxing on its paradisiac beaches, from the famous Varadero or some little Caye. Also, diving and snorkeling is possible.

Political tours

If you are interested in learning more about Cuba’s communism, join us to learn how this country transformed from Batista’s time to nowadays, and experience yourself the lights and darks of this country.

Afro-Cuban Dance tour

Immerse yourself in the rich Afro-Cuban music scene. Learn about rumba, son, and salsa through dance lessons and workshops. Attend local performances and experience the energy of Cuban nightlife. YPT can also organize a trip to Santiago de Cuba, the birthplace of son music.

Cigar Aficionado Tour

Visit renowned cigar factories, learn about the art of cigar rolling, and sample the finest Cuban cigars. Explore tobacco plantations in Vuelta Abajo, a region known for its premium tobacco leaves, and indulge in a cigar-tasting session with a local expert. 

Filming in Cuba
Through our media arm Pioneer Media we can make arrangements for productions, journalists, or others to film within Cuba from big budget to guerrilla productions. We can also arrange meetings in country, as well as correct visas for journalist wishing to do projects within Cuba.

Frequently asked questions about travel to Cuba

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