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Holidays to Trinidad, Cuba

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14 holidays match your criteria.

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This out of the ordinary group holiday travels overland across Cuba from tip to toe, meeting the people and in some places staying in family homes. Enjoy Havana, Trinidad and Santiago, the mountains of the Sierra Maestra, Caribbean beaches, Cuban music and dance, and gain an insight into the history of the island and the Cuban revolution.

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Havana & Western Cuba from CICERONI Travel. Well-paced and thorough exploration of Havana and its many facets. Visits to Havana’s art collections and Cuba’s houses and gardens. Excellent and well-situated 5 * hotels in Havana . Opportunity to explore the spectacular Valley of Viñales. In depth analysis of Cuba's history.

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Slow-paced Cuba, with unspoilt natural landscapes, is ideally explored on foot or by bicycle. Roads are mostly traffic free and trails explored only by the privileged few. On this private holiday you’ll cycle round the tobacco plantations, hike in the Sierra Maestra and trek up a table-mountain, exploring fascinating towns along the way.

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A full weeks exploring almost the whole of Cuba, from end to end, with your own private guide. The long loop through the heart of the island from Havana to Santiago is an amazing experience, capped by the gorgeous trip between the mountains and the sea to Baracoa.

  • Holiday duration: 15 days
  • Price from: £2,455
  • Operator: Geodyssey
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With over 300 stunning beaches, colonial architecture and a legendary history, Cuba is truly a gem of a destination to visit for any keen traveller. Experience Caribbean flavours and Latin vibes on our new tour taking you on a Cuban adventure that covers all of the highlights.

  • Holiday duration: 9 days
  • Price from: £899
  • Operator: Tucan Travel
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Cuba is a superb family destination: the distances are relatively short, roads outside the cities are traffic free, the people are friendly, and there are dozens of outdoor and cultural activities. And the sun almost always shines.

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This group holiday uses private transport and good quality hotels as well as private homestays to enhance your experience of this island story. Learn about the Cuban revolution, experience the thriving arts scene and admire colonial architecture being restored to its former finery. Hike out into tropical landscapes where time has stood still.

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We’ve devised a first class holiday where you will explore both by day and at night old Havana’s evocative historic quarters and Trinidad’s elegant colonial streets. Finally, you’ll soak up the sun on the chalky white sand beach at the Caribbean island Cayo Santa María, the largest and most developed of an archipelago of coral islets.

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This two week private tour of Cuba’s highlights goes a step further than most. Walk round Havana’s historic centre; stroll through limestone landscapes in the Viñales valley and forests around Las Terrazas. Move on to Cuba’s historic cities, Cienfuegos, Santa Clara and colonial gem Trinidad. Wind down on a sugary beach.

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