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

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.

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.

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.

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.

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.

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.