Overview & Highlights

This group holiday travels overland across Cuba from tip to toe, in some places staying in family homes. Enjoy Havana, Trinidad and Santiago, the mountains of the Sierra Maestra, and Caribbean beaches.

  • Baracoa: Yumari river
  • Santiago: Moncada Barracks
  • Bayamo: walking tour
  • Sierra Maestra: visit to Fidel's hideout
  • Sugar mills on route to Trinidad
  • Trinidad: walking tour
  • Santa Clara: Che's mausoleum
  • Viñales: walks in the Viñales valley
  • Havana: walking tour

Away from the all-inclusive resorts Cuba will capture your imagination and your heart. It is over 50 years since Castro's Revolution managed to both transform and petrify the island's society and economy. This holiday takes you to the authentic heart of the country - Cuba’s unique Latin American beat sets it apart from all the other islands of the Caribbean.

Crumbling colonial towns are characterised by dilapidated splendour, evocative of past elegance. The dusty alleys teem with barefoot boys playing baseball with bottle caps and rhythms pulsing out of every doorway. Vintage Cadillacs still roam the streets which, beyond Havana and a few trunk roads, are virtually traffic free. The youthful population has retained a natural exuberance, expressed in dance and music, which spontaneously breaks out day and night. The tropical scenery, unspoilt and pristine, is as stunning as it is varied, and the warm waters of the Caribbean lap against palm fringed beaches, enjoyed by local people and tourists alike.

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Holiday Extensions

If there's somewhere you particularly want to go that isn't included in this tour, we can add on an extension to take you there.

What our clients say

97% of our clients rated their experience with us as Excellent or Good.

It was a fantastic trip. There is an obvious division in Cuba between those who come into contact with tourists and those who don't and so, like a magnet around iron filings our very presence distorts and changes what we see. This is perhaps more the case in Cuba than elsewhere but as more people visit I hope this will reduce. It is, for the moment, part of the character of the country and part of the experience. I really can't fault the organisation of the trip and would just like to say again that our guide was fantastic at bringing the history and culture of Cuba alive for everyone.

RN, London

Tailor made holiday

Our specialists have been expertly crafting award-winning tailor-made holidays to Latin America for 40 years. We would be delighted to create a truly personalised trip which perfectly matches your wishes and requirements.

Sophie Barber
Sophie Barber - Travel Expert

Sophie lived in Chile before joining us and has travelled extensively across Latin America, from Mexico to the furthest tip of Patagonia and beyond to Antarctica.

tailor-make this trip

Inspired by this trip

Our exciting range of articles on Latin America explore everything from iconic destinations and lesser-known cultural gems to delicious traditional recipes. You’ll also find exclusive travel tips, first-hand client reviews and the chance to get your personal questions answered by our travel experts.

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Your edit for Latin American inspiration

Our exciting range of articles on Latin America explore everything from iconic destinations and lesser-known cultural gems to delicious traditional recipes. You’ll also find exclusive travel tips, first-hand client reviews and the chance to get your personal questions answered by our travel experts.

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Real Latin America Experts

  • Hannah Waterhouse
    Hannah Waterhouse - Travel Expert

    Hannah had an early introduction to Latin America when her family moved to Ecuador and she returned to study in Buenos Aires for a year before backpacking across the continent.

  • Chris Rendell Dunn
    Chris Rendell-Dunn - Travel Expert

    Anglo-Peruvian Chris grew up in Lima and spent much of his adult life in between London and Cusco as a tour leader, before settling permanently in our London-based Tailor-made and Group Tours sales team.

  • Hannah Donaldson
    Hannah Donaldson - Travel Expert

    Having spent part of her childhood in Colombia and worked in Brazil and Costa Rica, Hannah's ties to Latin America run deep. Hannah is a much valued Travel Expert in our Tailor-made Holidays and Group Tours sales team.

  • Paul Winrow Giffen
    Paul Winrow-Giffin - Travel Expert

    After graduating in Computer Science, Paul spent seven months travelling from Colombia to Argentina and came home hooked on Latin America.

  • Ben Line
    Ben Line - Travel Expert

    Ben fell in love with Latin America on a six month backpacking trip from Colombia to Mexico in 1995. Since then he has explored most of South America, including living in Peru for a year. He is now Head of Sales.

  • Lina Fuller
    Lina Fuller - Travel Expert

    Lina's passion for the continent where she was born really took off when she moved to Córdoba (Argentina) to study, spending the holidays travelling between Argentina and her native Colombia.

Meet the team