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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 60 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.

  • 11 days / 10 nights
  • Start dates: any date all year round
  • Cost: approx. £2550 per person, minimum 2 people

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.

B – Breakfast          L – Lunch        PL – Packed lunch        D – Dinner

Itinerary:

Day 1 – Arrive Santiago de Cuba (D)

Arrive Santiago de Cuba airport or bus station and private transfer to homestay accommodation including breakfast and dinner x 3 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 (B, D)

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). Afternoon guided visit of Moncada Barracks museum, where Fidel and his men made their fateful assault on the government troops on 26 July 1953, setting in motion the early steps for the Cuban Revolution.  Dinner at homestay and rest of evening free.

Day 3 – Santiago –  Gran Piedra, La Granjita (B, L, D)

Full day guided trip to visit la Granjita and the Gran Piedra. Located just 30 minutes outside Santiago is the Granjita former chicken farm where Fidel and his followers met to set off for Moncada Barracks. The house is now a small museum, with original items belonging to the revolutionaries and a selection of period photos on show and is a fascinating place to visit.

Very close by is the winding steep road up to the Gran Piedra, literally the ‘Big Rock’.   A sturdy metal ladder up to the top of the rock gives you amazing views over the sea, the countryside and down the coast all the way to Santiago. You will also visit the historic La Isabelica coffee plantation and museum and, if time permits, the Gran Piedra botanical garden. Lunch included in local restaurant. Return to Santiago late afternoon. Dinner at homestay and rest of evening free.

Day 4 – Santiago de Cuba – Turquino National Park  (B, D)

Private transfer after breakfast to the Sierra Maestra mountains and the hotel Villa Santo Domingo at the gateway to the Turquino National Park.  Half board accommodation x 2 nights.  This peaceful rural hotel is surrounded by tropical vegetation and is next to a small river where you can cool off in the rock pools. Rooms are spacious, with air conditioning, ensuite bathroom, tv, fridge and wifi is also provided.  Dinner at hotel and rest of day free.

Day 5 –  La Comandancia hike (B, PL, D)

0900 After breakfast, jeep/truck transfer from the hotel to the 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 your hotel. Dinner and rest of evening free.

Day 6 – Santo Domingo – Camagüey (B)

0830 Private transfer from hotel to  Playa los Colorados where Fidel and his men arrived by boat after exile in Mexico. Visit to the small outdoors museum telling the story of this historic landing and subsequent actions of the group.  Free time for lunch (not included) and continue with private transfer to Camaguey.  Arrive Camaguey late afternoon and check into your hotel accommodation including breakfast x 1 night.  Rest of day free.

Day 7 – Camaguey – Santa Clara (B)

0800 After breakfast, private transfer from Camaguey to Santa Clara to arrive mid afternoon. Check into private guesthouse accommodation, including breakfast x 1 night. Rest of day free.

Day 8 – Santa Clara – Bay of Pigs – Playa Larga (B, L, D)

0900 After breakfast, visit the Tren Blindado and the Che Guevara museum (museum closed on Mondays) with an English speaking guide. After lunch, private transfer to Playa Giron for a visit to the Bay of Pigs museum and then continue along the coastal road to Playa Larga, a small town on the edge of a lagoon. Check into local homestay including dinner and breakfast x 1 night. Rest of evening free.

Day 9 – Playa Larga – Havana (B)

0900 Private transfer from Playa Larga to Havana via a 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 guesthouse accommodation, breakfast included, x 2 nights. Rest of day free. 

Day 10 – Havana (B, L)

0900 Breakfast and half day guided visit on foot of Old Havana with a local guide, exploring the 4 main city squares and including a visit to either the Museum of the Revolution or the Museum of Bellas Artes where much of the artwork reflects pre and post Revolutionary politics.  Lunch in local restaurant (included) and rest of day free. 

Day 11 – Depart Havana (B)

Breakfast and free time to explore until private transfer to Havana airport. End of your Revolutionary Trail trip.

Cost:

From approx. £2,550 per person (2026 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.

Included:

  • Accommodation: 10 nights in licensed homestay/hotel accommodation with ensuite bathroom and air conditioning
  • Meals: meals included as indicated on the itinerary
  • Transport between cities: 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 travel visa (the required visa to enter Cuba as a tourist) – Caledonia can arrange this for you on request
  • Health and travel insurance
  • Tips/Gratuities

Vinales Valley, Pinar del Rio add-on tour

Duration: 3 days / 2 nights
Cost: £425 pp, based on 2 people sharing twin/double room accommodation

Single supplement of +£40 for single room accommodation

Description:

This 3 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; a spectacular sunrise walk to see the sun coming up over the silhouetted mountains and a guided tour of .

Itinerary:

Day 1 – Havana to Viñales
Depart Havana for Viñales by private transfer in the morning. Arrive Viñales around midday and check into homestay accommodation.   Light lunch at homestay.  Afternoon half day guided hike around the tobacco fields and visit to a local plantation to see how tobacco is processed. Continue the hike around the limestone mogotes, enjoying the impressive countryside and views over the valley. Return to Viñales late afternoon. Rest of day free.

Day 2 – Viñales

0530/0600 Your English speaking guide will meet you at your homestay this morning for a guided sunrise walk to see the sun rising over the mountains from a good viewpoint outside town.  The walk itself is not technically challenging and you should be back at your accommodation by around 1030 for breakfast. Remember to take a small torch or head lamp with you as it will be dark when you set off. It will be quite chilly at that early hour in the morning and we recommend that you take a jacket or jersey to wear for the first part of this morning.  It will warm up once the sun is up.  Take some water and a snack with you too.

Afternoon visit to Los Raices project, an ecological community project led by local artist Noel Dias Galá which offers an impressive open-air gallery.  Afterwards, you will also tour the “El Paraíso”farm with breathtaking views of the well-known Valle del Silencio and an opportunity to sample exquisite food made from products grown organically. Finally, you will visit the Botanical Garden of Caridad, featuring a wide variety of ornamental and medicinal plants.  Return to accommodation and rest of day free.

Day 3 – Vinales to Havana
After breakfast, depart by private transfer to Havana (approx. 3 hours). Arrive Havana.
-end of trip-

Included:

  • Transfers: private taxi from Havana – Vinales – Havana.
  • Accommodation: in specially selected homestays x 2 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, light lunch on day 1.
  • Excursions/Activities: as outlined in the itinerary with English speaking guide and transport where required. 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