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  • Trip Outline
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“Explore the history behind the famed Che Guevara and Cuba’s communist past and present”

Join Cuban Pioneers to celebrate with the Cuban people the quintessential person of the Cuban revolution, and symbol of revolutionary struggle around the world Ernesto “Che” Guevara.

This tour begins in Old Havana before we check out the Bay of Pigs, Mausoleum of “Che” which showcases his finals resting place and the famous train he derailed. We will also take part in celebrations that celebrate the life of Che, before heading over to Trinidad and then back to Havana. We then continue on our Che-themed tour heading out to San Carlos de la Cabana, where Che held his office (and even allegedly shot people that were sentenced to death), and resided for most of his life in Cuba.

For those that have been with YPT to the DPRK, we incorporate both the revolutionary theme and the relaxed atmosphere of Cuba, which gives you chance to explore free and if you so wish party to your heart’s content.

This tour is accompanied by YPT’s local representative and Cuban guide Roger, as well as a western guide and our very own bus for transport which stays with us for the whole journey. This means we have a lot of freedom with how we run the tour and gives us the opportunity to really get off the beaten path in rural Cuba.

Nothing stays the same forever, and Cuba is changing rapidly day by day, so see it with YPT now! As with all tours we can offer excellent discounts for YPT members, old customers, and group bookings.

Monday 5th November

  • Guests arrive/transfer to their homestay accommodation
  • Free afternoon in Havana
  • Meet up with group
  • Dinner and drinks in top local paladar (private restaurant)
  • Overnight in Havana

Tuesday 6th November

  • We start early, heading out to the historic city of Cienfuegos (a UNESCO world heritage site). The drive will take us about 5 hours and will pass the well-known Bay of Pigs.
  • The beginning of the journey will pass through many of Cuba’s citrus plantations, before heading into the swamps where boas and crocodiles live. If you want we also may have the chance to visit a crocodile farm at Boca de Guama.
  • 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.
  • Go with the guide or explore on your own.
  • Dinner in a local paladar private restaurant.
  • Night out drinking in the bars of Cienfuegos.
  • Overnight

Wednesday 7th November

  • Morning – walking tour around Cienfuegos. Visit the historic Teatro Tomás Terry.
  • Depart Cienfuegos for Trinidad – stop en route at Palacio de Valle, the outlandish house of an eccentric millionaire. (1.5 hours)
  • Lunch on arrival in Trinidad
  • We head off on our walking tour of Trinidad.
  • La Villa de la Santisima Trinidad was established in 1514. This is where the future conqueror of Mexico, Hernan Cortez, recruited sailors for his expeditions into the Americas. It is a super charming town with rolling green hills as its backdrop along with turquoise green waters and pure white sandy beaches, what more could you want? Until the 1800s this town was fairly quiet, then the influx of French refugees fleeing the slave revolt in Haiti landed here en masse and brought with them sugar cane cultivation. These new residents settled in Valle de los Ingenios located northeast of the town, where the area became the producer of one third of Cuba’s sugar cane created vast wealth. This was all brought to a halt though after two wars of independence
  • 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 you can see the remnants of the area’s once immense wealth in its grand colourful buildings. The town also saw a lot of action following the triumph of the revolution as gangs used the nearby mountains for safety.
  • Visit to The Museo Nacional de la Lucha Contra los Bandidos and the which chronicles the struggles of this period in the 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 infamous Disco Ayala, a nightclub in an underground cave!
  • Overnight in homestay

Thursday 8th November

  • Free day in Trinidad.
  • Suggested activities: trip to the beautiful Valle de los Ingenios in the morning (by classic train ($10), if it’s working), followed by afternoon horse riding or salsa dancing.
  • Other possibilities include a visit to the beach (Playa Ancón), salsa dancing lesson ($25) or just exploring the city.
  • Overnight in homestay

Friday 9th November

  • Today we travel 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 perhaps 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.
  • We 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

Saturday 10th November

  • In the morning, we return to Havana, making a stop in the open-air October Crisis museum which overlooks into Havana Bay. Here we can view the same type of Soviet missiles which almost brought on the end of the world (thankfully these missiles are now inactive).
  • Lunch in city
  • Visiting San Carlos de la Cabaña fortress where Che had his office.
  • Visit to the Havana Club Museum of Rum! Free samples optional
  • Meet up for dinner and evening out at the iconic Hemingway Bar amongst other places for an essential daiquiri to quench our thirst.
  • Overnight in homestay

Sunday 11th November

  • Breakfast
  • In the afternoon, we have a 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 pass the outdoor exhibit of the Museo de la Revolución to see the yacht Granma and learn about its importance in Cuban history.
  • We spend the rest of the day exploring the city and very much taking part in the biggest celebration of the year in Cuba.
  • Afternoon free time for some rest and relaxation or to wander some more.
    Dinner at our favourite secret private restaurant.
  • Optional but very strongly recommended visit to Fabrica de Arte Cubano (FAC – Cuban Art Factory, $2). This is one of the hippest art and night venues in the world right now.
  • Goodbye drinks, “Havana style” on the Malecon.
  • Overnight in homestay.

Monday 12th November

  • End of tour! It is completely fine to leave your things at the homestay whilst you either wait for your flight, or go exploring the city further. Cuban Pioneers can arrange a private taxi to the airport for you if you wish. Those continuing with the Vinales extension will be departing at 11am.
  • Accommodation: Every night of the tour.
  • Transport: To complete the itinerary.
  • Breakfasts: for each day of the tour, except the arrival day.
  • All lunches (excluding arrival and departure day)
  • Local English-speaking guide throughout.
  • Experienced, western Cuban Pioneer guide throughout.
  • All entrance fees as per itinerary


  • International flights
  • Visa/Tourist voucher (we can advise/provide depending on your passport and country of residence)
  • Insurance
  • All dinners (unless otherwise stated)
  • Drinks
  • Tips (we suggest $8 per day for guides and drivers)
  • Optional activities, day-tours and excursions (such as horse-riding and crocodile farm)