You choose when you want to go!


You choose when you want to go!


You choose when you want to go!


You choose when you want to go!


You choose when you want to go!


You choose when you want to go!

Havana, Cuba

Cienfuegos, Cuba

Santa Clara, Cuba

Trinidad, Cuba

Viñales, Cuba

Santiago de Cuba, Cuba

Camaguey, Cuba

Guantanamo, Cuba

We took over 45 people in 2014 and we’re now offering Cuba (aka“The Fairest Island Human Eyes Have Yet Beheld”) to anyone, anytime you want, any itinerary you want, year-round!

Design your own independent trip free from any fear of getting scammed, hassled, or simply trying to figure out things when you’re there, and we’ll take care of all the rest! Or join us and Cuban Pioneers for our classic annual trip for the Cuban celebration of May International Workers’ day, by far the biggest celebration in Cuba.

A sample itinerary will start you in Old Havana, before we go off to the Bay of Pigs and Cienfuegos. Then we head off to Santa Clara and the mausoleum of “Che”, where we not only see his final resting place, but the legendary train that he derailed in the final battle of the Cuban Revolution. Then it’s two celebratory days in Trinidad, after which we return to Havana for one final tour, or if you happen to go at the end of April – May DayThe whole of Havana (and Cuba) will take that day off to dance through the streets with their work parties listening to Latin-themed revolutionary music extolling the greatness of Fidel, Che, and Chavez, whilst the ruling Communist Party elite look down at us from the balcony (last year we got some great pictures of Raul and Fidel Castro waving down at us).

For those familiar with us, we stick with a revolutionary theme, but 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. The tour is accompanied by Cuban Pioneers’ local Cuban guide, as well as a western guide, and our very own bus that will accompany us for the duration of the journey, meaning lots of flexibility and chances to get very off the beaten Cuba track. And as with all tours we can offer excellent discounts for YPT/MD members, old customers, and group bookings.

Nothing stays the same forever, and Cuba is changing rapidly day by day, so see it with us now!

Optional 2-Day Extension: We also offer an exclusive 2-day extension where numbers will be strictly limited; we will be visiting en route some locations not normally open to tourists, including an abandoned nuclear missile bunker from the heyday of the Cuban Missile Crisis, as well as the Soviet Internationalist Memorial and Mausoleum. We will also head to the western part of Cuba, where we stay in the famous town of Viñales in its beautiful mountain setting, with nearby secluded beaches, and a visit to a tobacco plantation where we discover the secrets of the world’s best cigars.

Contact us for more information!

For a day-by-day visual experience of one of our Cuba trips, click here: Cuba
…or start with our first day: You’re Going to Miss…“The Fairest Island Human Eyes Have Yet Beheld.” (Part I)
For a day-by-day visual experience of one of our Cuba trips, click here: Cuba
…or start with our first day: You’re Going to Miss…“The Fairest Island Human Eyes Have Yet Beheld.” (Part I)

Monday 25 April

  • Guests arrive/transfer to their homestay accommodation
  • Free afternoon in Havana
  • Meet up with group
  • Dinner and drinks in the old town
  • Overnight in Havana

Tuesday 26 April

  • Early morning the group departs for the historic city of Cienfuegos (5 hour drive via Bay of Pigs)
  • On the way to Cienfuegos we firstly travel along the flat central plain of Cuba where there are lots of citrus plantations. We turn off the main highway and shortly after this 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 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 home restaurant
  • Night out drinking in the bars of Cienfuegos
  • Overnight

Wednesday 27 April

  • Depart Cienfuegos for Trinidad
  • The beautiful colonial city of Trinidad is home to numerous churches and many beautiful colonial buildings.
  • Optional activities include swimming in waterfalls, horse riding, diving, salsa dancing class, and a visit to Playa Ancón, where you can enjoy long stretches of unspoiled, white sand beaches. Another option is a steam train ride to the beautiful and historically important Valle de los Ingenios (Valley of the Sugar mills).
  • Group dinner in a local Cuban home, obviously accompanied by rum.
  • 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

Thursday 28 April

  • We head off on our 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 and the Casa de los Mártires de Trinidad chronicles the struggles of this period in the town’s history.
  • Lunch in city
  • Return to homestay for some rest and free time
  • Free afternoon to explore the city
  • Group dinner and night out in Trinidad – we will be visiting the very famous underground cave night club for a great night out.
  • Overnight in homestay

Friday 29 April

  • 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.
  • We stop at a very beautiful and secluded waterfall on the way, with al fresco swimming followed by rustic local lunch at a farmers house.
  • 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.
  • Dinner and optional evening of local music.
  • Overnight in Santa Clara

Saturday 30 April

  • 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.
  • 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
  • Meet up for dinner and evening out at the iconic Hemingway Bar amongst other places
  • Overnight in homestay

Sunday 1 May – May Day!

  • Breakfast
  • Trip Highlight: Group meets up early to join the walk to the May Day March & celebration in Havana. Hopefully seeing Fidel! This is by far the biggest celebration of the year, and by far the biggest May Day celebration in the world. We will be very much part of this! Last year we were lucky enough to see Raul waving down at us from the balcony.
  • Lunch in the city
  • 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
  • Goodbye drinks, Havana style, on the Malecon
  • Overnight in homestay

Monday 2 May

  • 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 the Haiti Extension we can arrange an extra 2 nights accommodation at a discounted rate.

This is a trip that was co-planned and co-led by The Monsoon Diaries and Cuban Pioneers in 2014. Crediting to that trip’s success, we are happy to sponsor this as a recurring trip led and planned fully by Cuban Pioneers. Therefore, this is now a trip separate from The Monsoon Diaries (hereafter referred as “MD”) with no MD staff present on tour. We secure exclusive sales agreements with Cuban Pioneers whereby we can advertise and sell these tours at a significant discount to the customer.

Please note that this discount can only be secured when the booking is made though The Monsoon Diaries. Contact us for information on other tours run by these companies as we may be able to offer further discounts across all tours!

Cuban Pioneers is a separately run company independent of The Monsoon Diaries. Payment for all tours booked with Cuban Pioneers follows our own set of terms and payment conditions. Cuban Pioneers cannot under any circumstances accept payment by Paypal, Moneybookers, US-backed credit cards, or US-based bank transfers. Please contact us to discuss other options if this presents any difficulty.

Price inclusive of:

  • Accommodation: Every night of the tour.
  • Transport: To complete the itinerary.
  • Breakfasts: for each day of the tour, except the arrival day.
  • Dinner: 1 group dinner in a local homestay.
  • Local English-speaking guide throughout.
  • Experienced, western Cuban Pioneer guide throughout.
  • All entrance fees as per itinerary
  • Unlimited rum in homestay

Price exclusive of:

  • International Flights
  • Visa (we will advise you depending on your passport and country of residence)
  • Insurance
  • All meals (except for 7 breakfasts and one homestay group meal)
  • Drinks
  • Tips
  • Optional activities, day-tours and excursions
  • Departure taxes ($25CUC/person) and excess baggage fees

Our Previously Organized Independent Tours

May 2015: Dina Patel

“Flags up!”

May 2014: 40+ people

Click here for trip reviews.

May 2015: Amanda Chan & Samantha Stein

“Adventures in a beautiful land!”

July 2015: Jenny Chu & Charles

Sept. 2015: Maria Thomas, Alex W, Bryan T, Jeff K, Nick C, Justin C, and Matt A

“Couldn’t have found a better group to help me cross off my top bucket list item. Love you boys and your Goldbond, boxers and cigars.”

May 2016: Dominica Lim & Saraswati

“Snow White & her 7 dwarves!”

April 2017: Michelle Duncan, Kel Sage, Ms. Davis, Mr. Duncan

“Calvin, we’re back…had a blast!” – Duncan

“I had a great time. Nothing could be [more] perfect. I have several friends and family members who are interested in vacationing in Cuba. I’ll pass on your information to them. Once again thank you for planning a fun fill[ed] trip.” – Davis

April 2017: Ihita K., Kristina M., Tesha F., June K.

April 2017: Iris C. & Robert L.

April 2017: Jolie Yang, Naomi, Katie, Martin, and Misha

“[The trip] was absolutely wonderful, really got a feel for Cuba and reading about the Bacardi’s during my trip made it that much more alive…”

May 2017: Lei Z., Yoni R., & Friends

“. . . May Day in Havana was the other primary highlight of the trip, and in my eyes, it was truly a unique spectacle to behold. I’m not sure if any other socialist nation takes the day as seriously as the Cubans do (China certainly doesn’t), and you definitely won’t see anything of this scale in the Western Hemisphere. . . .” — 2017 May Day in Cuba; First Impressions — In Context With Venezuela, written by Lei Zhao

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