Revolutionary Road Trip

2-Week Self Drive Cuba Holiday Itinerary - Havana to Cayo Levisa

Prices from £1,488 pp

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Duration15 days / 14 nights (flexible)


ItineraryHavana - Santa Clara - Trinidad - Playa Larga - Vinales - Cayo Levisa - Havana

Call us 01273 322398


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.

What's included

  • Accommodation – price based on 2 people sharing
  • Breakfast
  • Cuban visa (tourist card)
  • Tours as described
  • Economy car hire for 10 days with air con and roadmap

Our ready-made itineraries 1. Add your favourite itinerary to your travel plan  2. Send it our way 3.Our travel specialists will get planning and send you a quote

Location map

Your day-by-day itinerary

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.

Classic Cars in Havana

Cuba, the Cuban 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.

Cuba, the Cuban Way

Discover Nature's Paradise

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.

Playa Largo

Rolling through Tobacco Hills

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.

man jumping in the air in vinales, cuba

Cosy Cayo Levisa Island

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.

Cosy Cayo Levisa Island

Final night in Havana

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.

local man riding bike in streets of cuba

Speak to our Cuba specialist, Emma

"Cuba is one of the most fascinating countries in the world. With its vintage charm, friendly locals and music on every corner, it is often described as stepping foot into a living museum. It's not hard to fall under Cuba's spell."

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