Cuba May Day Revolutionary Tour

5 days / 8 days / 10 days     25 Apr, 2026 – 11 Apr, 2026

5 days / 8 days / 10 days      25 Apr, 2026 – 11 Apr, 2026     Price:US$ Home

one country
Unforgetable

Start Date

25 Apr, 2026

End Date

11 Apr, 2026

Duration

5 days / 8 days / 10 days

Price

595

Join YPT for our classic annual trip, joining in the Cuban celebration of May International Workers’ Day, by far the biggest celebration in Cuba, something like a Soviet-era parade with a good dose of Latin American carnival spirit!

If you’ve already seen May Day in North Korea, then this is something completely different! The whole of Havana (and Cuba) takes the day off, and you’ll join them cheering through the streets, listening to Latin-themed revolutionary music extolling the greatness of Fidel, Raúl and Che, while the ruling Communist Party elite wave down at us from the podium. This is the most memorable time to be in Cuba, and a truly amazing once-in-a-lifetime experience. We will also visit the towns of Cienfuegos and Trinidad, as well as the Che Mausoleum in Santa Clara.

It is an extremely interesting time to visit Cuba, as it is just ushering in a post-Castro era and we will make sure to get that impression straight from the people on the streets.

The tour is accompanied by Cuban Pioneers’ local Cuban guide, as well as a western guide, and we also incorporate the much more relaxed environment that Cuba offers us by giving ample time for free exploration as well as providing a great chance to party the night away as much as you wish. Nothing stays the same forever, and Cuba is changing rapidly day by day, so see it with us now!

If that is not enough for you, we offer our Group B extension, where you’ll visit some very unusual Communist/Soviet locations (such as the secret site of the nuclear missiles during the Cuban missile crisis) before heading to the countryside where you can explore Viñales. Continue your tour with us to Colombia!

Tour Highlight

  • 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 Australia Sugar Mill where Fidel Castro oversaw the military operations

  • Get all things Ernesto Guevara at the Museum and Mausoleum of Che in Santa Clara

Included

    Excluded

      GroupStart dateEnd dateDurationPriceSingle Supplement

      Group A: Full tour

      25 Apr, 2026

      4 May, 2026

      1295

      320

      Group B: Cienfuegos, Trinidad, Sta Clara, Havana May Day

      25 Apr, 2026

      2 May, 2026

      945

      245

      Group C: Havana May Day, Secret bunkers, Viñales

      30 Apr, 2026

      4 May, 2026

      595

      130

      Print Itinerary

      Full Itinerary

      Saturday 25th April – Havana

      Morning

      • Group A & B members: arrive at own leisure and transfer from Jose Martí International Airport to the Vedado part of Havana.
      • An official taxi from the airport is USD$25. Alternatively, Cuban Pioneers can arrange meet-and-greet pickup 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.

      Afternoon

      • The group assembles at around 8:00pm for our introduction into the contemporary night scene of modern Havana.
      • 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 sea wall, known as the “sofa of the city”
      • Overnight in Vedado

      Sunday 26th April – Cienfuegos

      Morning

      • Early morning the group departs for the historic city of Cienfuegos
      • 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 timing we take a stop at a famous crocodile farm which a chance to feed the friendly reptiles and even have photos with them (optional extra charge)
      • 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 sinkhole which resembles a huge natural tropical fish tank, so make sure to pack your swimwear. SCUBA diving and snorkelling are optional activities here.

      Afternoon

      • We take our lunch Cuban style by the beach, before carrying on the journey
      • On arrival you in with your host family, we will then have an opportunity to have a walking tour of the city. 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 ambience to inspire Cuba’s most celebrated Son singer to write the words “Cienfuegos is the city I like best”.
      • We head for dinner at a very famous Cuban family restaurant that is very unpretentious and serves great food
      • Night out drinking in the bars of Cienfuegos, with clubs available for the truly thirsty ones.
      • Overnight Cienfuegos

      Monday 27th April – Cienfuegos – Trinidad

      Morning

      • Depart Cienfuegos for Trinidad which is a short 90 minute, or so journey
      • The beautiful colonial city of Trinidad is home to numerous churches and many beautiful colonial buildings. On arrival here we stop for lunch at renowned pizza restaurant whilst your guides arrange our casa in the city
      • After checking-in to our rooms in old part of the town we head out for a walking tour of the historic city of Trinidad, including the old town centre, an official cigar shop, and a slightly dodgy back alley one where cheap cigars are available. We finish off with another classic revolutionary museum before heading for some refreshments, which consists of the local Trinidad cocktail.

      Afternoon

      • We take some time to relax and get changed before heading out for the evening
      • We head to a trendy restaurant which serves contemporary fusion cuisine
      • 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.
      • Overnight in homestay

      Tuesday 28th April – Trinidad

      Morning

      • In the morning we head to the Valle de Los Ingenios, the valley of the sugar mills, where the wealth of Trinidad came 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.

      Afternoon

      • After a hard day in the sun, we offer a few hours to relax before again hitting the town
      • There are a number of options for dinner depending on the hunger and mood of the group
      • At night we head to one of our favourite places in the world, the infamous Cave Nightclub (one of the most legendary in Cuba) for a night of debauchery.
      • Overnight in Trinidad

      Wednesday 29th April – Santa Clara

      Morning

      • Today we travel to the city of Santa Clara, which was a key city in the triumph of the Revolution (3-hour drive)
      • 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.
      • We stop at a genuine tobacco farm to see the process of how farmers make the worlds most famous cigars, and for the adventurous try a little of the produce ourselves. This is a very uniquely Cuban experience

      Afternoon

      • Upon entering Santa Clara there is a huge statue of Ernesto Che Guevara, beneath which is the mausoleum where his remains are buried, as well as seeing the museum that is dedicated to “Che” the most iconic of all revolutionary figures
      • We stop at one of the highlights of Santa Clara, the train that Che derailed during the revolution, which not only makes for a great picture stop but if you like Che hats and t-shirts this is tac heaven.
      • Santa Clara is a nice town to spend the evening in, so after dinner, we head to El Mejunje, which is a famous local cultural centre with live music, comedy, and cabaret that very few foreigners visit.
      • Overnight in Santa Clara

      Thursday 30th April – Havana

      Morning

      • Group C members: Arrival in Jose Martí International Airport at your convenience to meet the group in Havana. An official taxi from the airport is USD$25. Alternatively, Cuban Pioneers can arrange meet-and-greet pickup for $50, or arrive in real style in a classic convertible for $95.
      • Group A & B members: We head back to Havana in the morning, stopping at the 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.

      Afternoon

      • Lunch in city
      • In the afternoon we have a city tour of Havana, encompassing the Plaza de 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 Revolución to learn more about the revolution and its history.
      • Visit to the Havana Club Museum of Rum! Free samples optional
      • We head back to our casas to freshen up for our last night in Havana
      • For dinner we get ourselves all Presidential by heading to one of the restaurants where the Obamas dined. We will be taking a leisurely one hour stroll to the restaurant, or for those wanting to pimp it up a bit we offer optional hire of a Soviet-era limousine.
      • Farewell drinks in the old town, with optional nightclub activities for those with the energy
      • Overnight in homestay

      Friday 1st May – Havana – International Workers’ Day

      Morning

      • Trip Highlight – It’s party time, so we have breakfast at 6 am before leaving at 6.30am sharp!
      • We head to the outskirts of the Plaza De Revolución where the festivities will be starting to begin to soak up some atmosphere and get ready for the start of the parade
      • The actual parade starts at around 7.30 am, where we will join around a million Cubans parading through the plaza in a quintessentially Cuban fusion of fiesta and old-school communist procession. We’ll get a wave from the top leadership of Cuba, including former president Raúl Castro.
      • We end proceedings at the baseball stadium (previously visited by Obama) where we will be met by our bus for the drive to Old Havana

      Afternoon

      • Lunch in old Havana
      • We head for a relaxed walking tour of Old Havana which includes various churches and some of the best Spanish colonial era architecture available anywhere in the world, including our favourite the Bacardi building!
      • No trip to Old Havana would be complete without a bucket list trip to Hemingway’s favourite bar, the birthplace of the daiquiri cocktail.
      • We head back to the casa for some rest and a change after the early start, or for those not so tired some beers on the Malecón
      • In the evening we head for dinner at the famous Soviet-Cuban fusion restaurant, one of the legacies of Cuba’s cold war past complete with borsch, perogi and more Soviet propaganda than you can shake a stick at
      • Drinks in Havana
      • Overnight

      Saturday 2nd May – Viñales

      Morning

      • Group B members: tour concludes. We can arrange your airport drop-off according to your flight details – YPT is also able to arrange post-tour accommodation or advice for flights.
      • Group A & C members: continue and depart at 9:00am 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!

      Afternoon

      • 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 in to 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.

      Sunday 3rd May – Viñales

      Morning

      • 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

      Afternoon

      • 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 hours 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

      Monday 4th May – Viñales – Havana

      Morning

      • Head back to Havana after breakfast (3 hours drive) where the tour concludes for all groups
      • For those not continuing to Colombia, with YPT able to arrange extra accommodations, flights and other adventures in the Caribbeans and Latin America!

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