Cuba New Year: Che Guevara and Missile Base Tour

8 days / 10 days     26 Dec, 2026 – 4 Jan, 2027

8 days / 10 days      26 Dec, 2026 – 4 Jan, 2027     Price:US$ 995 / 1345

one country
Unforgetable

Start Date

26 Dec, 2026

End Date

4 Jan, 2027

Duration

8 days / 10 days

Price

995 / 1345

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

Group Start Date Finish Date Duration Price (USD)
Group A 26th December 2026 2nd January 2027 8 days $995
Group B: Viñales 26th December 2026 4th January 2027 10 days $1345

The trip begins in the iconic, time-warped capital Havana, home to a contemporary night scene. So naturally, this will include sampling some of Cuban's national drink – rum and afterwards staying in a homestay for a memorable experience.

While many are drawn to the capital, we want to show off the country beyond the iconic town. So, we head out, stopping at the icy clear waters at the Bag of Pigs en route to the UNESCO world heritage city of Cienfuegos. Since Cuba is home to some of the coolest scuba-snorkelling-swim opportunities, especially the sinkhole that resembles a natural tropical fish tank, we strongly encourage bringing swimwear and your camera.

This trip also takes us to the city of Trinidad, known for its colonial old town and cobblestone streets. Here you'll get the opportunity to engage in the city's history at The Museo Nacional de la Lucha Contra Los Bandidos, which also has a tower with the best view. Later you get to watch and, if willing, participate in the city's live music and dance. You may even visit one of the coolest nightclubs, Disco Ayala, built into a natural cave.

Ensuring we take in the best of the nation, we then journey to Santa Clara city, visiting the most significant historical sights and staying overnight. Then, heading back to Havana, we show you the best and wackiest sides of the town. Followed by dinner at our favourite (and best) restaurant, which we keep top secret for our YPT guests.

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. Here you'll discover why Cuba is famous worldwide as the gold standard of cigars at a tobacco farm; of course, you’ll have the opportunity to sample! Further, we get intrepid in visiting the less populated, stunning caves.

Tour Highlight

  • Visit Santa Clara and see the 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, where we even see the train that Che derailed during the revolution!

  • Explore the Bay of Pigs, including the Australia Sugar Mill where Fidel Castro oversaw the military operations

  • New Year party in Havana!

Included

  • Accommodation on twin-share basis
  • Transport to complete the itinerary
  • Breakfasts and light lunches (excluding arrival and departure day)
  • Local English-speaking guide and western Cuban Pioneer guide throughout
  • All entrance fees as per itinerary

Excluded

  • International flights
  • Single supplement (US$35 per night)
  • Visa (YPT can provide full assistance)
  • Travel Insurance (mandatory)
  • All dinners
  • Drinks and personal expenses
  • Tips for the guide
  • Airport transfers
GroupStart dateEnd dateDurationPriceSingle Supplement

Group A

26 Dec, 2026

2 Jan, 2027

8 days

995

Group B: Viñales

26 Dec, 2026

4 Jan, 2027

10 days

1345

Print Itinerary

Full Itinerary

Saturday 26th December – Havana, Cuba

Morning

  • Group arrive at own leisure and transfer from Jose Martí International Airport to the Vedado part of Havana.
  • An official taxi from the airport is about US$50. Alternatively, YPT can arrange meet-and-greet pickup in an old 1950s American car for an extra cost.
  • 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 7:00pm 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 seawall, known as the “sofa of the city”
  • Overnight in Vedado

Sunday 27th December – Havana – Cienfuegos

Morning

  • 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 have the opportunity to 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.

Afternoon

  • 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

Monday 28th December – Cienfuegos – Trinidad

Morning

  • 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)

Afternoon

  • 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

Tuesday 29th December – Trinidad

Morning

  • 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

Afternoon

  • 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

Wednesday 30th December – Trinidad – Santa Clara

Morning

  • 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.

Afternoon

  • 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

Thursday 31st December – Santa Clara – Havana: New Year’s Eve!

Morning

  • 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.

Afternoon

  • 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

Friday 1st January – Havana: New Year’s Day

Morning

  • Breakfast at homestay and begin our city tour of Old 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 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

  • Afternoon free time or rest for those weary. Our guide is able to 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, $5). This is one of the coolest art and night venues in the world right now.
  • Drinks, Havana style, on the Malecón
  • Overnight in homestay

Saturday 2nd January – Havana – Viñales

Morning

  • Group A 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 B members continue and 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!

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 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

Sunday 3rd January – 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 January – Viñales – Havana

Morning

  • 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.

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