• Overview
  • Trip Outline
  • Trip Includes
  • Trip Excludes
  • Booking

“Come explore both Cuba and Colombia, two of Latin Americas fastest changing places, rich with history and culture!”

Join Cuban Pioneers for the annual May Day celebrations for International Worker’s Day. This is by far the biggest national holiday in Cuba with celebrations galore in true Latin-Soviet style. We then continue on to explore the stunning scenery of Colombia following the history of the FARC through the capital Bogota and the cocaine capital Medellin!

We’ll also be celebrating YPT’s 10th Anniversary!

If you have seen May Day in the DPRK, then prepare to be blown away again as Cuba puts on a completely different show! The whole country has the day off to dance through the streets listening to Latin-themed revolutionary tunes, which showcase their admiration for Fidel, Che, and Chavez, all done under the gaze of the ruling Communist Party elite. There’s no better time to be in Cuba and is definitely an unforgettable experience. Throughout this trip, we will also make our way to the towns of Cienfuegos and Trinidad as well as the Che Mausoleum in Santa Clara.

The tour is led by our Cuban Pioneer’s local Cuban guide as well as an experienced western guide. We take advantage of Cuba’s relaxed atmosphere by allowing ample free time for exploring as well as providing plenty of opportunities to party the night away. As with all YPT tours, we have amazing discounts on offer for returning customers and group bookings!

Cuba won’t stay like this forever, come and see this amazing country as it goes through some rapid changes on a Cuban Pioneers tour!

And if that is not enough for you, Cuban Pioneers have an exclusive two-day extension in the famous town of Viñales.

Colombia might have had a chequered past, with landmines, and the remnants of the civil war and organized crime still very much omnipresent, but Colombia is slowly waking from its past and hitting the challenges of reform head-on

Monday 30th April

  • Arrive at own leisure and transfer from Jose Martí International Airport to the Vedado area of Havana.
  • Official taxis from the airport cost CUC$25, or we can arrange a for you to be picked up in an old 1950s American car for USD$50. For those really looking to travel in style there is even an option to be picked up in a classic convertible for USD $95.
  • Upon arrival, your guide will show you to your homestay (complete with A/C and hot showers), where you will have free time to mingle and get to know the others in the group over a local beer or two.
  • We meet up at 8pm for an introduction into the contemporary nightlife of modern Havana.
  • For dinner, we will be heading to Café Laurent, one of the oldest and (in our opinion) best private restaurants in the country with a range of options to fit all budgets.
  • In true Cuban-style, we finish the evening by grabbing a carton (or two) of rum and head out to people watch on the Malecón (Havana’s famous seawall known as the “sofa of the city”).
  • Overnight in Vedado

Tuesday 1st May – International Workers’ Day

  • #TRIP HIGHLIGHT# It’s party time! We get up early for breakfast at 6 am before leaving a 6:30am on the dot!
  • We head to the outskirts of the Plaza De Revolución, where the locals will already be starting to celebrate. This is time to soak up the atmosphere as we wait for the start of the parade.
  • The Parade starts around 7:30, this is your chance to join 1 million Cubans as they celebrate May Day in true Cuban fashion dancing to a mix of Latin communist fusion beats! We will even get a chance to see the top leadership of Cuba waving to us, including outgoing President Raúl Castro!
  • The procession will end at the baseball stadium (which was previously visited by Obama) where our transport will meet us to take us to Old Havana.
  • Lunch in old Havana
  • After lunch, we head out for a walking tour of old Havana, including various churches and some of the best Spanish colonial architecture available, including our favourite the Bacardi building.
  • It would be a shame to come all this way and not go to Hemmingway’s favourite bar, so we head there to celebrate the birthplace of the daquiri cocktail.
  • We head back to our homestay for a rest, or if you’re not tired head out for some more beers on the Malecón.
  • In the evening, we head out for some Soviet-Cuban fusion cuisine, complete with borsch, perogi and all the Soviet propaganda your heart desires.
  • Drinks in Havana
  • Overnight

Wednesday 2nd May

  • Early morning the group departs for the historic city of Cienfuegos.
  • On the way, we stop off at some unmissable places such as the Australia Sugar Mill where Fidel commanded activities during the Bay of Pigs invasion.
  • On the way to Cienfuegos we stop off at a few places of interest such as the Australia Sugar Mill which is where Fidel commanding activities during the Bay of Pigs invasion.
  • Depending on available time, we stop at a famous crocodile farm where we will have a chance to feed and take photos with them (optional extra charge).
  • We will travel past the picturesque Caribbean coast making our way along the Bay of Pigs, the landing site of counter revolutionary exile militia in 1961.
  • We visit the museum dedicated to this conflict, which marks the first defeat of a US-backed takeover in Latin America. We stop at some amazing spots for swimming along the way, including a sink hole that feels like a giant tropical fish tank so don’t forget your swimwear! Optional Snorkelling and SCUBA diving activities will be available.
  • We have a Cuban-style lunch at the beach, before continuing our journey.
  • On arrival we will settle in with our host family, then we will have an opportunity to take a walking tour of the old city. Cubans are very proud people and the citizens of Cienfuegos refer to their town as “La Perla del Sur” or “Pearl of the South”. With wide Parisian-style boulevards and majestic colonnades this place was inspiring enough to have a song written about it: “Cienfuegos is the City I Like Best”.
  • We head out for some true local food at a Cuban family restaurant with amazing options for dinner.
  • We check out the nightlife by hitting up the bars of Cienfuegos, complete with clubbing options for the truly wild ones.
  • Overnight

Thursday 3rd May

  • Depart Cienfuegos for Trinidad which is a short 90 minute, or so journey
  • The colonial city of Trinidad is adorned with many churches and stunning colonial architecture. On arrival, we stop for lunch at a famous pizza restaurant whilst your guides head into town to arrange your homestay.
  • We head into the old part of town where we will check into our rooms, before heading out for a walking tour of this beautiful and historic city, including an official cigar shop and a slightly dodgy back alley shop where cheap cigars are available for those on a budget. We hit up another revolutionary museum before quenching our thirst with the local “Trinidad cocktail”.
  • We take some time to relax and get changed before heading out for the evening.
  • We head to a restaurant called La Redacción which serves contemporary fusion cuisine.
  • Nightlife here in Trinidad is the most open and intense of all Cuba, with endless live music venues and dance performances all week long, all of which is set amongst charming old colonial buildings and cobblestone streets.
  • Overnight in homestay

Friday 4th May

  • In the morning, we head out to Valle de los Ingenios (Valley of the sugar mills) where Trinidad gained its wealth from in the 1800s.
  • In the afternoon, we offer a number of optional activities such as horse riding to a waterfall, salsa lessons, or free time to explore Trinidad at your own leisure.
  • After a hard day sightseeing we have the option to rest for a few hours before heading out again on the town.
  • There are plenty of dining options for dinner depending on the mood and hunger of the group.
  • Later in the evening we head to one of our favourite places, the infamous Cave Nightclub (one of the most legendary in Cuba) for a night of fun and madness.
  • Overnight in Trinidad

Saturday 5th May

  • In the morning, we hit the road again (3 hours) to Santa Clara, which was a key city in the triumph of the revolution.
  • Depending on the road conditions we will take a number of different routes through the Sierra del Escambray, making a some stops on the way.
  • We will stop off at a tobacco farm to see how the world’s most famous cigars are produced, and for those that wish we can try some ourselves.
  • Upon arrival in Santa Clara we will visit the massive estate of Ernesto Che Guevara, beneath which is the mausoleum where his remains are buried. We will also make a visit to the museum dedicated to “Che” the most iconic of the revolutionary figures.
  • We stop at another of Santa Clara’s highlights, the rain the Che derailed during the revolution, which makes for great photos and is the perfect spot to pick up some Che-themed souvenirs.
  • In the evening, we will head out for dinner and afterwards to El Mujemje, a famous local cabaret and comedy centre that few foreigners visit.
  • Overnight in Santa Clara

Sunday 6th May

  • We make our way back to Havana, stopping at the open-air October Crisis museum which overlooks Havana Bay, featuring Soviet nuclear missiles (now thankfully inert) from 1962 when the world came close to all out nuclear war.
  • Lunch in city
  • In the afternoon we have a city tour of 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 visit the famous Museo de la Revolucion to learn more about the revolution and its history.
  • Visit to the Havana Club Museum of Rum! Free samples optional.
  • We head back to the accommodation to freshen up and have a rest.
  • For dinner, we will put on our best and head to one of the restaurants visited by the Obamas. We will make our way here by a leisurely one hour stroll or for those wishing to go all out optional hire of a Soviet-era limousine.
  • Farewell drinks in the old town, with optional nightclub activities for those with the spare energy.
  • Overnight in homestay

Monday 7th May

  • Depending on the Cuban bureaucracy we will aim to leave at 11:00am.
  • Our first stop is the first statue of Lenin ever erected after his death on Lenin Hill. This is very rarely visited by tourists.
  • Lunch at a Cuban style street restaurant
  • #TRIP HIGHLIGHT# We now make a trip to the incredibly secret bunker where the Soviet Union stored nuclear weapons during the 1980s Cuban Missile Crisis. As well as being incredibly hard to find, this place has only recently been discovered and therefore open to tourists, however very few come to visit!
  • In the Afternoon, we take a look at former Soviet embassy, which is an impressive piece of Soviet architecture. We will also see some other Soviet-era tower blocs which make for some great photos of Havana’s rich history
  • Afterwards we go on the 2-3 hour drive to Viñales. Upon arrival, we check into our accommodation before heading out to dinner and drinks in what used to be a sleepy town and now has bustling nightlife.
  • Overnight in Viñales

Tuesday 8th May

  • 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 renowned for its stunning caves, a number of which are quite popular with tourists which we avoid like the plague, instead we grab our local guide and use his knowledge to take us to a cave that is still relatively untouched by outsiders. This will take an hour’s hike through the cave network with lights before we get to the swimming part of the adventure. This part of our journey is absolutely amazing, so don’t forget your go-pro!
  • Afterwards we head back for a quick shower, then we head out to a great vantage point to enjoy our last sunset with a well-deserved cocktail as a group.
  • We finish our last night in Viñales with an authentic home cooked Cuban meal at our homestay.
  • Drinks and conversation in the rocking chairs on the patio to end our last evening.
  • Overnight.

Wednesday 9th May

  • Head back to Havana after breakfast
  • End of Vinales extension tour.
  • Check into Havana homestay
  • Evening – optional visit to an elite private nightclub to party with sons and daughters of generals and colonels.

Thursday 10th May

  • Late breakfast
  • Visit some unusual Havana sights
  • We head to Jose Marti monument in Revolution Square. Nearly all tourists visit this site from the outside with few actually entering the inside. It is now however possible to go to the top of the monument, which is the highest point in the city of Havane. This is also the closest that tourists can get to the Palace of the Revolution where the Communist Party elite used to run the country from. You can even glimpse into the office of Raul Casto!
  • Dinner then head to the airport for late flight to Bogota.
  • Free evening and overnight in Bogota.

Friday 11th May – Bogota

  • We meet up with others joining the Colombia section of the tour then head straight out to the Military Museum, where we can learn about Colombia’s lesser known role in the Korean War.
  • We take a stroll around the Parque Simon Bolivar and see what the locals get up to in their spare time.
  • We make a quick stop by the Congress and the Supreme Court. These are the same buildings that were seized by Marxist guerrillas in 1985.
  • Lunch in the city
  • We visit the Colon Theatre, which is where the peace process between the government and FARC was signed. We then visit the Museo Banco de Republica, the main modern art museum in Colombia.
  • We head to Southern Bogota, the blue-collar area of the city to endulge in some people watching.
  • Later, we head to dinner and then for an authentic Friday night salsa in the Colombian capital. If you’re not a good dancer that won’t matter as there will be ample amounts of rum to boost confidence.
  • Overnight in Bogota

Saturday 12th May – Sierra Nevada National Park

  • In the early morning, we take a quick 2 hour flight to Cartegena.
  • On arrival, we transfer directly to the Sierra Nevada national park. This national park is home to many of Colombia’s indigenous peoples as well as the country’s most diverse biosphere.
  • Lunch in Sierra Nevada
  • Many opportunities to explore the area and its wildlife.
  • In the evening, we will camp out in the reserve complete with a BBQ and of course rum!

Sunday 13th May – Sierra Nevada National Park

  • We head out to the Wiwa Indian Reserve to visit the local indigenous people in the mid-highlands to learn their way of life.
  • Local lunch with the Wiwa
  • We head back to Cartagena, where we check into the hotel before heading out for dinner to a Peruvian restaurant and drinks in Café Havana
  • Overnight in Cartagena

Monday 14th May – Cartagena

  • We explore the old colonial city of Cartegena and learn about its rich history.
  • We have a look at the old city walls as well as the Spanish-era coral stone forts which are over 500 years old.
  • Lunch at Interno, a restaurant staffed by former political prisoners
  • Climb La Popa Hill for a great view of the area and visit the 17th century Santa Cruz monastery
  • We then head over the Spanish Inquisition Palace, a place where people were tortured and killed for crimes against Catholicism.
  • Head out for local food and drinks in the Cartagena old town
  • Overnight in Cartagena

Tuesday 15th May – Medellin

  • In the morning at 10am we board a flight to Medellin, the second city in Colombia.
  • Medellin is infamous for being home to the notorious drug lord Pablo Escobar. Since the mid-1990s things have calmed down a lot and it is now a safe place to travel.
  • In the afternoon, we head out to the Museo de Antioquia which hosts the world-famous sculptures by Fernando Botero in the grounds surrounding the museum.
  • Go for dinner and drinks in Medellin
  • Overnight in Medellin

Wednesday 16th May – Medellin

  • Breakfast in the hotel before we jump on our bus to begin the tour of Medellin
  • In the morning we drive out to visit a project that helps farmers change from cocoa growing to coffee, part of the plan to eliminate the drug trade in Colombia.
  • Lunch in a roadside almuerzo
  • After lunch, we visit a village that until recently was riddled with landmines. Thanks to a charity however the place has been demined. This is a great opportunity to learn about the impact the civil has had on the local people.
  • Before dinner, we meet 2 former FARC soldiers who discuss their experiences during the civil war.
  • Dinner and overnight in Medellin.

Thursday 17th May – Medellin

  • In true Medellin fashion we head out to learn about its most famous resident, Pablo Escobar.
  • We begin the Escobar tour in La Paz, the birthplace and old stomping ground of Pablo Escobar, led by an expert local guide.
  • We then see the other side of his life exploring many of the luxurious buildings used for various money laundering operations. We will also check out his bombed-out safe in the Monaco Building, where the first car bomb in Colombia was detonated.
  • After visit the “Cathedral” (Pablo’s old prison), we go to see some spectacular views and the private cemetery where siblings and cousins of the mafia boss finally rest.
  • We end the tour by taking a trip out to the infamous La Manuela Mansion where the drug lord lived out his over-the-top lifestyle.
  • We take a boat over to the mansion where we will have enough free time to explore, take photos, and who knows maybe bump into a Hippo.
  • Overnight in Medellin.

Friday 18th May

  • We get up early for our morning flight to Bogota, where the tour ends, with YPT being able to arrange ongoing transport or accommodation for those that need it.


  • Accommodation
  • Breakfasts and lunches
  • Transport including domestic flights
  • Experienced YPT guide and local English-speaking guide


  • Flight from Havana to Bogota
  • Accommodation


  • International flights
  • Visa (YPT can provide assistance)
  • Insurance
  • All dinners
  • Drinks and personal expenses
  • Tips for the guide


  • International flights