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Revolutionary Road Trip


  • Itinerary:
    Havana - Santa Clara - Trinidad - Playa Larga - Vinales - Cayo Levisa - Havana
  • Duration:
    15 days / 14 nights (flexible)
  • Price:
    from £ 1,448.- per person (excluding flights)
Jump in your hire car and take a road trip through beautiful Cuba. You’ll begin amongst the rum bars of Havana before exploring the cobbled streets of Trinidad. Next, you’ll journey into the countryside to roll through Cuba’s famous tobacco fields and discover nature trails jam-packed with hidden delights. Top it all off with a mojito on a white-sand beach and leave your worries behind you.
Cuba classic red car in the street
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Days 1-4 – Classic cars in Havana

Havana has a distinct, exotic personality that you won’t find anywhere else on the planet. During this trip, you’ll stay in a local Casa particular near the heart of timeless Old Havana. You’ll take a city tour by classic car and foot, it’s the perfect way to explore the mix of crumbling colonial beauty, peeling bygone glamour and colossal Caribbean soul.

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Days 4-8 – Cuba, the Cuban way

Once your time in Havana has come to an end you’ll pick up your hire car and drive to Santa Clara. The driving time is around 3 hours, but you might like to make a few stops along the way. Get lost in a colonial daydream and dust off your dancing shoes on the cobbled streets of Trinidad. During this trip, you’ll spend one night in Santa Clara on your way to Trinidad, for a visit to Che Guevara’s mausoleum. In both places, you’ll stay with a family in a traditional Casa Particular. You’ll take a bici-taxi tour with a local guide, getting you into the groove of this creative, colourful and quirky city.

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Days 8-10 – Discover nature’s paradise

Back in your hire car, you’ll drive to Playa Larga, another journey of about 3 hours. On Cuba’s south coast you’ll find a scattering of small villages rarely visited by tourists. On the surface, there doesn’t seem to be much on offer, just a few restaurants, hotels and Casas – where you will be staying. However, during your time here you’ll discover the area’s hidden secrets. Head out with a local guide to discover a nature trail jam-packed with flora and fauna, Cuba’s deepest freshwater cave and shoals of exotic fish.

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Days 10-12 – Rolling through tobacco hills

From Playa Larga it’s about 4.5 hours to Vinales, so you might like to make a stop for lunch along the way. Horse ride through the rolling hills of Viñales, Cuba’s rustic cigar region. You’ll stay in a local Casa, explore the valley on horse and foot and learn about the art of cigar-rolling whilst meeting the local guajiros. If you’re looking for an authentic experience, you’ve found it. Life isn’t staged in Viñales, it simply unfolds.

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Days 12-14 – Cosy Cayo Levisa Island

Next, you’ll drive from Vinales to Cayo Levisa. The driving time is approx. 30 minutes to the ferry port at Palma Rubia. From here you’ll catch the ferry to Cayo Santa Maria. Cayo Levisa Island is a little nook of beach bliss off Cuba’s northern coast. Heading for the island, you’ll be following in the footsteps of Hemingway, who discovered this archipelago on a fishing trip from the next islet along, Cayo Paraiso. You’ll spend two nights in a basic resort on Cayo Levisa, dozing under a coconut palm, collapsing into a lounger and cooling down with a dip in the bright blue sea. It’s sun-drenched, secluded and downright dreamy.

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Days 14-15 – Final night in Havana

We’ll arrange your ferry back to the mainland where you’ll hop back in your hire car and make the journey back to Havana. The drive back should take about 2 hours. You’ll return to Havana and stay in Havana Vieja. This is your chance for a final wander and to visit any sites you may have missed previously. The many art galleries and local craft markets mean you can stock up on any last minute souvenirs. Maybe you’ll have time to visit some of Hemmingways’ old haunts as well.

It’s your last day in Cuba, so we’ll help things run more smoothly by arranging a private transfer to take you to the airport. The journey shouldn’t take more than an hour.

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Revolutionary Road Trip