Walking Holiday in Cuba

In late December 2025, Anjna Patel and two friends, Rob and Natasha S, travelled with Caledonia Worldwide to Cuba. They were on a two week walking and cultural holiday,  planned and organised over many months of discussion. They travelled from one end of the island to the other and the following are their comments after the trip.

‘Overall, Cuba was a fantastic and highly recommendable experience. Despite the current challenges, we met some incredibly warm, welcoming people with a strong sense of community and pride in their mixed heritage and culture. In the context of what’s going on politically in the UK, US and Europe, this was genuinely refreshing and grounding.

We really valued learning about Cuba’s history through the lived experiences of our hosts, guides and drivers. Hearing different perspectives added depth and made the journey feel personal rather than just observational. The history and culture are rich and fascinating, and well worth experiencing, even with the realities of power cuts, shortages and visibly run-down cities.

We felt very safe throughout the trip. While there was some begging and opportunism, it was no more than you’d experience in many other countries and never felt threatening.

Tourism was clearly much quieter than usual, which was great for us as travellers but also sad to see given the impact on the local economy. Conversations with locals reflected a range of views on why the country is struggling – sanctions were cited, but many also felt this was an excuse and internal leadership could be doing more.

Food was mixed and perhaps the most disappointing part of the trip although we did have some amazing meals. Breakfasts and lunches included on excursions were generally very good and tasty, but finding good restaurants for evening meals were more challenging. Vegetarian options were limited and bland at these places.  We’d expected bolder Caribbean flavours, but meals were generally quite bland, likely due to ongoing food supply shortages rather than lack of care or skill.

All in all, we loved Cuba and would definitely recommend it. It may not be an easy destination for some right now – but it’s a deeply human, eye-opening and rewarding one if you go with an open mind, curiosity and realistic expectations.

Old Havana was excellent and an absolute must-see. Despite the visible hardships, the city is full of friendly, relaxed people and has a powerful atmosphere.  Seeing Old Havana in such a state of disrepair was confronting at first, but it  only deepened our appreciation of its beauty and history.  The chosen homestay was outstanding. Our hosts were incredibly warm and welcoming, offering practical help and making the stay very comfortable. The house was well equipped for power cuts, with reliable electricity, hot water and WiFi, and breakfasts were generous, tasty and vegetarian-friendly.

The guided walking tour was a highlight. Ivan was an excellent guide – friendly, engaging and highly knowledgeable – bringing Old Havana to life through history, culture and his own perspectives. The restaurant selected for lunch was also excellent, with a beautiful setting and very good food.

While fuel shortages and crumbling buildings were clearly visible, none of this detracted from our experience. Old Havana remains a deeply compelling, unforgettable place and one we would strongly recommend as an essential part of any trip to Cuba

Viñales was a real highlight and a must-do, with spectacular scenery, peaceful rural life and wonderful walking. Waking up to farm sounds and walking through the valley and farmed land was a memorable experience, and the sunrise hike was particularly special – well timed, not overly crowded and very rewarding.

The chosen homestay was excellent: comfortable rooms, welcoming hosts, good breakfasts with fresh local fruit, and a backup generator that meant power cuts had little impact. Even walking back in the evenings by torchlight felt safe and atmospheric.

The planned valley hike and sunrise trek were both highly recommended, offering great insight into traditional farming practices and daily rural life.

The Bay of Pigs Museum in Playa Giron is well worth including. The guide did not speak English, but he communicated slowly and clearly in Spanish so that I could translate for my friends. He also offered valuable personal insight. The El Nicho jeep safari and guided walk were highlights – well paced, scenic and led by an engaging local guide who shared history, ancestry and honest perspectives on life in Cuba. Lunch at El Nicho was adequate but limited, particularly for vegetarian options.

Trinidad was one of the real jewels of the trip and an absolute must-see. The town has a wonderful sense of community – guides, drivers, shop owners and restaurant staff all seemed to know one another, creating a friendly, relaxed and welcoming atmosphere. We loved the cobbled streets, rich history and getting happily lost in the maze-like lanes, especially in the evenings.Accommodation was initially in a guesthouse located opposite the main house. I had issues with the toilet in my room, but the housekeeper was extremely responsive and promptly relocated us to the main house. The rooms there worked well and were more comfortable than those in the smaller guesthouse, especially during the power cuts. Breakfasts were good, and although power cuts and patchy WiFi occurred, these were manageable. The housekeepers at the accommodation were very friendly and accommodating.

The guiding here was exceptional. Alejandro (Topes de Collantes) and Elvis (Valle de los Ingenios) were both highly engaging, knowledgeable and passionate. The Topes de Collantes hike was a standout experience and a definite must-do, with beautiful scenery and insightful commentary. Alejandro’s unplanned guided walk around Trinidad afterwards was a highlight, helping us understand the city’s architecture, social history and culture in depth. Elvis also added value with personal stories and historical context during the Sugar Mill Valley excursion. Planned lunches and chosen restaurants were wonderful with vegetarian options and well seasoned food.Overall, Trinidad stood out for its atmosphere, people and outstanding guides, and we would strongly recommend including it – along with a guided walking tour and the Topes de Collantes hike – in any Cuba itinerary.

Bayamo became one of the most memorable parts of the trip for us. Following the advice from the Caledonia Worldwide local representative we met in Havana, we spent time walking through a residential neighbourhood, where we connected with local residents, and were able to distribute donations directly to families. The experience was deeply moving, especially seeing how much support was needed for children.

Our hike in Santo Domingo was an excellent and highly recommended activity, offering a very authentic glimpse into rural Cuba. A real hidden gem, the walk through the valley – along the river, across rocks and through farmland – felt special, particularly as we were the only visitors there. Although the museum was closed due to fumigation, this didn’t detract from the overall experience.

Visiting a local farm was a real highlight, with demonstrations of traditional sugar cane juice extraction and coffee preparation adding cultural depth and insight into daily life. An unexpected pig chase by hunting dogs, as we were having a dip in the river, gave us a memorable and very real glimpse of rural life.

Lunch was simple but tasty, enjoyed with beautiful views over the valley.

The guide was pleasant but relatively quiet, offering less storytelling and broader context than some of the other guides we met. However, he was younger, and with more experience and confidence we’re sure he will provide an even richer guided experience.

The driver was friendly, communicative and reliable, which helped make the day run smoothly.

Santiago de Cuba was excellent and a real must-see, with a very different energy and cultural feel from Havana. We would happily have spent an extra day here. The transfer from Bayamo ran smoothly, with a friendly and punctual driver.

The homestay was well located and the hosts were welcoming, and the housekeepers too. However, there were challenges with inconsistent hot water during power cuts. Santiago overall felt more impacted by power outages and food shortages than other places we visited, with some restaurants closing when electricity was down.

The guided activities were a real highlight. Our guide was warm, knowledgeable and flexible, and we really enjoyed spending time with her. The visit to El Cobre and Cimarrón Hill was fascinating, followed by a wonderful lunch at La Terraza de Caridad, with tasty food, good vegetarian options and an entertaining coffee and cigar presentation.  We also appreciated being taken on an unplanned walking tour of the city, with our guide showing us her old neighbourhood, Revolution Square and the main sights. We ended the day by watching New Year’s Eve celebrations and the flag ceremony in the main square,  a memorable way to experience the city’s spirit.

Despite some practical challenges, Santiago de Cuba left a strong impression and is a destination we would highly recommend including in any itinerary.

Outstanding planning and support throughout. Kath was incredibly patient, knowledgeable and thoughtful, really taking the time to understand what we were looking for and creating a well-balanced itinerary. The pre-departure information was excellent and went above and beyond with practical tips, and everything ran smoothly as planned.

Would we recommend Caledonia Worldwide?  Absolutely – without hesitation.

We would strongly recommend including a guided walking tour in each city, as we found this invaluable for getting our bearings and for understanding how the history, culture and everyday life are connected. Where possible, a small list of locally recommended restaurants by budget would also be very helpful, as this was perhaps the most challenging for us, although we understand this is personal.

Highlights of the trip

Too many to choose just one, but standouts included:

• Old Havana guided walk
• Viñales sunrise hike and valley walks
• Topes de Collantes (Guanayara hike)
• Trinidad city walk
• Santo Domingo hike
• Santiago de Cuba lunch with coffee & cigar heritage at La Terrazza and city walking tour
• Bayamo distributing donations