• Overview
  • Trip Outline
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  • Trip Excludes
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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’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.

*Tour highlights*

  • Join around a million Cubans celebrating May Day, looking somewhere between a Soviet-era parade and a classic Latin American carnival!
  • Explore the Bay of Pigs, including the Australian Sugar Mill where Fidel Castro oversaw the military operations
  • Get all things Ernesto Guevara at the Museum and Mausoleum of Che in Santa Clara

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 1 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 May 2nd

  • 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 May 3rd

  • 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 May 4th

  • In the morning, we head out to Valle de loc 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 May 5th

  • 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 May 6th

  • 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 May 7th

  • 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.
  • For those joining our Vinales extension we will be leaving at 11.00 am
  • Accommodation
  • Transport to complete the itinerary
  • Breakfasts for each day of the tour, except the arrival day and all lunches (excluding arrival and departure day)
  • Local English-speaking guide and experienced, western Cuban Pioneer guide throughout
  • All entrance fees as per itinerary
  • International flights
  • Visa (YPT can provide assistance)
  • Insurance
  • All dinners
  • Drinks and personal expenses
  • Tips for the guide