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Cuba Tour: Cuba’s Revolutionary Trail

This fascinating 10 day itinerary, discovering Cuba’s Revolutionary Trail, follows in the footsteps of Fidel and Che. It provides a detailed insight into the history of the Cuban Revolution, on a voyage of discovery through this beautiful and intriguing island.

Over 50 years ago, Fidel Castro and his followers triumphantly drove into Havana, declared that the revolution had been successful and thus a new era in the history of Cuba was about to begin.  You will have a unique opportunity to see firsthand what those changes are and how they have influenced everyday life in Cuba.

  • 10 days / 9 nights
  • Start dates: any date all year round
  • Cost: from £2550 pp, minimum 2 people (2023 price)

Please keep reading for full details.

“We really enjoyed this trip and loved the variety of places we visited. Our guides were all really great and we really appreciated being able to learn much more about what has made Cuba the incredibly unique place that it is. Gracias!’

DT, Glasgow

Revolutionary Trail outline itinerary

We start the trip in Santiago de Cuba, the second city of the island. Often called the ‘cradle of the revolution’, where Fidel and his followers gained most popular support in the fifties and plotted to overthrow the Batista regime, this is also the city where Fidel has been laid to rest. We continue to historic Bayamo, one of the original 7 cities founded by the Spanish, and then on to the Sierra Maestra mountains to visit La Comandancia, the secret base where Fidel planned and commanded revolutionary activities in the fifties.

From here we travel up the island to Camaguey, Santa Clara and the Bay of Pigs, visiting the most significant and interesting historical sites along the way. Our itinerary then finishes in Havana, the capital of this fascinating island.

Cuba’s Revolutionary Trail is a customised itinerary which can be adapted to suit your specific interests and budget, and can start at any time of the year, subject to availability.


Day 1 – Arrive Santiago de Cuba

Arrive at Santiago de Cuba airport and private transfer to homestay accommodation including breakfast and dinner x 2 nights. Depending on your time of arrival, you may be able to have a short orientation walking tour with a local guide after arrival. Dinner this evening at homestay and rest of evening free.

Day 2 – Santiago de Cuba

Breakfast at accommodation. Morning guided city tour including a visit to the Moncada Barracks; Santa Ifigenia cemetery where Fidel Castro is buried and the Jose Martí mausoleum can be found; San Juan Hill and the Vista Alegre district.  Free time for lunch (not included) and then continue up into the Sierra Maestra mountains to visit La Granjita, where Fidel Castro and his men hid-out before storming the Moncada Barracks. Return to Santiago for dinner at homestay. Rest of evening free.

Day 3 – Santiago –  Bayamo

Morning free to visit the Moncada Barracks, where Fidel and his men tried to first overthrow the Batista government, or the Museum of the Resistance.  Free time for lunch (not included). Late afternoon travel by bus from Santiago to Bayamo and check into homestay accommodation including breakfast and dinner x 2 nights. Dinner at homestay and rest of day free.

Day 4 – Turquino National Park: La Comandancia 
Early breakfast and depart by private transfer with  your guide to Santo Domingo, the gateway to the Turquino national park.  Jeep/truck transfer from here to trail head to hike to La Comandancia de la Plata, Fidel’s secret base in the mountains with local specialist guide (3km each way). Picnic lunch included. Climb up to visit Radio Rebelde (if time allows), the radio station established by the revolutionaries, before returning to the trail head and transfer back to Bayamo.  Dinner at homestay and rest of evening free.

Day 5 – Bayamo – Camagüey

Travel to Camagüey this morning by private transfer. Arrive Camagüey mid afternoon and met by local guide for short walking tour of historic centre, before checking into your homestay or hotel accommodation including breakfast x 1 night. Rest of day free.

Day 6 – Camagüey – Santa Clara

After breakfast, free time until midday travel by national bus from Camagüey to Santa Clara. Arrive late afternoon and private transfer to homestay accommodation, including dinner & breakfast x 1 night. Rest of day free.

Day 7 – Santa Clara –  Bay of Pigs – Playa Larga

After breakfast, visit the Tren Blindado and the Che Guevara museum  with an English speaking guide, and free time for lunch (not included). Private transfer after lunch to Playa Giron for a visit to the Bay of Pigs museum and then continue along the coastal road to Playa Larga. Check into local homestay including dinner and breakfast x 1 night. Rest of evening free.

Day 8 – Playa Larga – Havana

Private transfer from Playa Larga to Havana via the community called Australia where there is a small museum dedicated to the Cuban defence of the Bay of Pigs. On arrival into Havana, check into private guesthouse accommodation, breakfast included, x 2 nights.

Day 9 – Havana

Half day guided visit on foot of Old Havana with a local guide, exploring the 4 main city squares and visiting the scale model of the city. Lunch in local restaurant (included) and afternoon guided visit to the Museum of the Revolution. Evening visit to experience the cannon ceremony at El Morro castle overlooking Havana Bay at 9pm, with return transport provided.

Day 10 – Depart Havana

Breakfast and check out of accommodation. Private transfer to Havana airport and the end of your Revolutionary Trail trip.


From £2,550 per person (2022/3 price), based on 2 people sharing twin/double room accommodation.
The cost of this itinerary depends on the number of people travelling together and the period of travel as well as other factors such as variations in accommodation.


  • Accommodation: 9 nights in licensed homestays with ensuite bathroom and air conditioning
  • Meals: meals included as indicated on the itinerary
  • Transport between cities: on national tourist buses and private transfers where indicated
  • Excursions/visits: All entries and transport for visits and excursions with English speaking local accredited guides.

Not included:

  • Flights are not included in the cost of these holidays and should be booked independently.
  • Cuban tourist card (the required visa to enter Cuba as a tourist) – Caledonia can arrange this for you on request unless you are travelling from the US in which case you will require a different travel visa
  • Health and travel insurance
  • Tips/Gratuities

Vinales Valley, Pinar del Rio

Duration: 4 days / 3 nights
Cost: from £220 per person, based on 2 people sharing twin/double room accommodation


This 4 day tour extension takes us to the beautiful Viñales Valley which lies west of Havana, where world famous tobacco is grown and the impressive limestone mogote cliffs rise out of the rich red earth. This itinerary lets us discover the picturesque region including a hike around the mogote cliffs and a visit to a tobacco plantation; and a visit to the Cueva Santo Tomas – the largest and most impressive cave in Cuba.


Day 1 – Havana to Viñales
Depart Havana for Viñales by bus in the morning. Arrive Viñales early afternoon and make way to homestay accommodation. Rest of day free

Day 2 – Viñales
After breakfast, met by English speaking guide for half day guided hiking around the tobacco fields and visit local plantation to see how tobacco is processed. Continue the hike around the limestone mogotes, enjoying the impressive countryside and views over the valley, rustic lunch included. Return to Viñales late afternoon. Rest of day free.

Day 3 – Viñales
Depart Viñales after breakfast with your English speaking guide for your full day excursion to the Cueva de Santo Tomas, the largest cave in Cuba with 46km of caves full of impressive stalactites, stalagmites and bats.

Day 4– Vinales to Havana
After breakfast, depart on the bus to Havana (approx. 3 hours). Arrive Havana.
-end of trip-


  • Transfers: by public bus from Havana – Vinales, and Vinales – Havana.
  • Accommodation: in specially selected homestays x 3 nights in double or twin room. All rooms have air conditioning and private bathroom. Hotel accommodation may be available on request for a supplementary charge.
  • Meals: breakfast at homestay each day, rustic lunch on day 2.
  • Excursions/Activities: 1 full day and 1 half day excursion/activity with English speaking guide and transport where necessary. Entrances included.

Not included

  • International flights and airport transfer – Caledonia can arrange this for you on request.
  • Cuban tourist card (the required visa to enter Cuba as a tourist) – Caledonia can arrange this for you on request.
  • Health and travel insurance
  • Any services or meals that are not included/stated in the itinerary
  • Tips/Gratuities

‘Really good. Nice to get out into the countryside and good “through the window watching” during transfers. Very relaxing. Guide was great so would definitely recommend the trip to others’.

SL, Nottingham

‘ The thing I liked about this trip was that for me (as an experienced independent traveller) the balance was right between hand-holding and organisation, and having the freedom to do my own thing when I wanted to’.

LS, Edinburgh