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.

Cuba is a fascinating country and JLA have pulled together a fantastic trip with excellent local guides. It exceeded my expectations and I do hope to return one day.

AES, Eastbourne

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 Consultant

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

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.

Papagaio

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.

View Extraordinary Inspiration

Real Latin America Experts

  • Sophie Barber
    Sophie Barber - Travel Consultant

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

  • Hannah Waterhouse
    Hannah Waterhouse - Travel Consultant

    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.

  • Carrie Gallagher
    Carrie Gallagher - Travel Consultant

    A former JLA tour leader, Carrie brings a wealth of on-the-ground experience to our London-based Escorted Groups team.

  • Mary Anne Nelson
    Mary Anne Nelson - Travel Consultant

    Born in the Atacama Desert in northern Chile, Mary’s insider knowledge and dry sense of humour make her a highly valued member of the Tailor-made team.

  • Kathryn Rhodes
    Kathryn Rhodes - Travel Consultant

    Kathryn backpacked across Argentina, Chile, Bolivia and Peru before joining us. She has a degree in Philosophy and French and is a keen netball player.

  • Chris Rendell Dunn
    Chris Rendell-Dunn - Travel Consultant

    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 Sales team.

Meet the team