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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What our clients say

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

All of the Parakeet was fantastic.

LS, 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.

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.

tailor-make this trip

Accommodation

Browse our unrivalled portfolio of accommodation . Every option has been carefully chosen by our team of travel experts, so you can rest assured that you’ll relax in utter comfort.

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.

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.

  • Evie Oswald
    Evie Oswald - Travel Consultant

    It’s hard to believe that Evie has had time to cram so much in to her life so far. Having lived as a child in the Americas and Europe she found herself immediately attracted to Latin America.

  • Ben Line
    Ben Line - Travel Consultant

    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 Manager of the Tailor-made Department.

  • 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.

  • 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.

  • Lina Fuller
    Lina Fuller - Travel Consultant

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

Meet the team