It appears that your web browser does not support JavaScript, or you have temporarily disabled scripting. The Explore website requires JavaScript enabled to operate correctly.

Find a trip

Where would you like to go?
What type of trip do you like?
When would you like to go?
More search options
622 Matching trips
Site Search

Customer Feedback

Read reviews


Discover our latest brochures available online now, with hundreds of adventures to choose from.


Be the first to hear about great new tours, competitions, special offers and unique departures.

Gift Vouchers

The perfect gift idea for any occasion. Send gift vouchers and create fantastic memories with vast trips and experiences to choose from.

Tailormade Classic Colonial Cuba

Castro, Cuba Libre's and old cars
With quiet, open roads, a great selection of hotels and a variety of colonial towns, a self-drive holiday in Cuba is an excellent way to explore the country at your own pace.  Enjoy a cocktail and watching old cars go by in Havana, discover the mojotes of Viñales and get lost in Trinidad’s colonial streets.  With photo stops wherever and whenever you like, a self-drive holiday is a relaxing and flexible way of seeing Cuba.

Enriching tailormade journeys – for you
This bespoke journey features some of our favourite spots in Cuba. You can choose to take our destination experts’ recommendations and travel just as you see the itinerary here, or contact us to add your own special touches; the beauty of a self-drive is the great flexibility you have, you may choose to upgrade your car or extend your stay in another town. We’re here to design your perfect holiday. Call us on 0844 875 1896.

hanna holmes thumb

Meet Hanna Holmes, 
Regional Specialist for Cuba

Call on 0844 875 1897

Please click one of the trip style options below to see more detailed information about the accommodation available.

Tailormade Classic Colonial Cuba - Authentic Version

Show more
  • 1 Fly to Havana

  • 2 Havana

  • 3 Drive to Vinales

  • 4 Explore Vinales

  • 5 Drive to Trinidad

  • 6 In Trinidad

  • 7 Explore Trinidad further

  • 8 Drive to Havana

  • 9 Depart Havana