Group Holidays

With a unique political history, pristine sandy beaches and restored colonial towns, Cuba is the ideal destination if you want to embark on a trip to remember.

Cuba group holidays give you the perfect opportunity to explore the largest of all the Caribbean islands with like-minded travellers. Experience stunning landscapes, connect with its rich culture of music and dance, or relax on white sandy beaches.

Our group holidays to Cuba have small group sizes of up to 20 people, and are accompanied by one of our exceptional tour leaders at all times.

We update our tours regularly using our first-hand knowledge and feedback provided from our tour leaders and customers. We also arrange your accommodation, most meals, main excursions and land transport to make sure you maximise your time discovering the best of Cuba. Explore our full range of holidays to Cuba for even more inspiration.

Our Parakeet: Cuba beyond the beach escorted group holiday takes in the authentic heart of the country – Cuba’s unique Latin American beat sets it apart from all the other islands of the Caribbean. Stay far away from the all-inclusive resorts, explore Havana, Vinales, Cienfuegos, Trinidad and Santa Clara.

Contact our Travel Experts if you feel inspired to join an escorted group holiday in Cuba. With almost 40 years of experience in organising trips to Central and South America, you can trust us to book a holiday to remember.

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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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Meet our team

Real Latin american experts

  • Sallly
    Sally Dodge - Travel Expert

    A former Journey Latin America tour leader, Sally spent 7 years working, travelling and living throughout Latin America before returning to the UK to help people arrange their own adventures to this wonderful destination.

  • Paul Winrow Giffin
    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.

  • Juliet
    Juliet Ellwood - Travel Expert

    After graduating with a degree in Anthropology and History and having been fascinated by Latin America since childhood by the book featuring photos of Nazca, Juliet first visited the region in 2003. Since then, Juliet has visited the majority of countries in Latin America but has particularly extensive experience with Peru, a country she loves for many reasons but not least, its incredible archaeological richness and delicious food!

  • Sophie
    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.

  • Maggie
    Maggie Wilson - Travel Expert

    Maggie visited Latin America on her first backpacking trip when she was 19. Since then, she has taken every opportunity to travel, and has managed to explore a lot of the region in subsequent trips.

  • Mary
    Mary Anne Nelson - Travel Expert

    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 Holidays and Group Tour sales team.

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