Classic Western Cuba
Who: Couples and Solo Travellers

10 Days

From $4,785pp

Classic Western Cuba

Ollie is here to help give you the inside track.

Get under the skin of Latin Americas's most fascinating nation on this cultural ten-day tour around Cuba

Itinerary at a Glance:

  • Trace the history of Cuba from the Spanish colonial years to present-day Communism
  • Learn the art of cigars in Vinales
  • Explore colonial Cuba on horseback

Why Book with Original Travel?

Just a few of the extra touches that come as standard on an Original Travel holiday...
Our Local Concierges
100% Carbon Off-Setting
One Point of Contact
Hold Airline Seats
Expert Guides
24 Hour Helpline
See More

When To Travel













Average temperature -
Average rainfall -

All of the holidays we create are completely tailor-made to you

This sample itinerary is intended to give you a flavour of what we can do

Day 1: Arrive in Cuba

Once you land in Cuba today, one of our team on the ground will meet you at the gate and whisk you through the formalities, before your private transfer to your charming casa particular (guest house).

Day 2: Behind the Scenes

Today you will go behind the scenes of life in Havana with a private local guide.

Begin by joining the locals for coffee at a hole-in-the-wall coffee bar before heading off to explore the backstreets and secret squares of the city. Your guide will explain how the half-a-century Communist rule, coupled with local creativity, has shaped the city and the way people live here.

This evening, we have secured you queue-jump tickets for the Fabrica de Arte Cubano (FAC, in the local vernacular), an arts space which hosts performers and exhibitions of all shapes and sizes. On any given night, you could see a salsa band, an Avant Gard theatre group or a contemporary art exhibition. Or all three!

Day 3: Architecture Tour

To get even deeper under the skin of Havana, this morning you will be privately transferred to Vedado, a bustling area in Havana's downtown district where you'll spend the next three nights.

Bags dropped off in your room, you will meet your expert architect guide for a private trip through Havana's architectural history. Conservation-minded Cuba's capital is a living time capsule of buildings which represent its many ages, from the Rat Pack Rococo Riviera hotel (built 1959) and the Castillo de la Real Fuerza (a fortress completed in 1588) to the Soviet-style edifices of the Castro years, including the Russian Embassy - designed by the USSR's 'People's Architect' Aleksandr Rochegov. As you wander through the streets your guide will explain how the people and, more importantly, politics of Havana have shaped its buildings over the years.

Day 4: Tobacco Trip

Today you will make a day trip to Vinales, an open-air classroom in which you will learn everything you could possibly want to know about Cuba's most famous export: the cigar

After a two-and-a-half hour drive west of Havana, you will visit a tobacco plantation among the enormous lime karsts that punch out of the landscape like enormous sugar loaves. With a local farmer you will follow the life cycle of a tobacco plant, from seedling to rolling your own cigar, then head back to Havana in time for a late supper.

Day 5: Art Tour

Spend this afternoon exploring Fusterlandia, the brainchild of Cuban artist Jose Fuster, in the far west of Havana.

Fuster has been transforming the Jaimanitas neighbourhood into a Gaudi-esque open air museum since 1975, decorating doctors' surgeries, bus stops and houses with whimsical mosaics. If he is at home, you will get to meet him and chat about this inspirational - and initially almost accidental - regeneration project. Head back into the centre of twon and spend this evening at El Cocinero and its downstairs space - Fabrica De Arte Cubano, a multi-disciplinary gallery, theatre and concert venue.

Day 6: Havana to Cienfuegos

Today you will leave Vedado and be privately transferred two-and-a-half hours south east, to the coastal town of Cienfuegos. Spend the rest of the day relaxing by the sea before dinner.

Day 7: Mangroves and More

It's a change of pace from city life today as you head to the mangroves in the lagoon of Guanaroca, just outside Cienfuegos.

The lagoon forms part of a nature reserve which is home to countless birds, including the Cuban trogon, the country's national bird, and 2,000 pink flamingos.

After your visit to the mangroves, you will head to Trinidad, an hour further east and your home for the next two days.

Day 8: Horsing Around

Today, your guide will meet you at your hotel for a horseback tour of the Valle de los Ingenios (Valley of the Wits).

As you explore the region and the sugar plantations with in it, your guide will explain how little has changed here for decades (if not centuries) and how it got such an interesting name.

Spend the rest of today ambling around colonial Trinidad, enjoying its beautiful squares and buildings.

Day 9: Beach Bums

Spend today on the beach at Ancón, about nine miles away.

Our local concierge will recommend the best spot to catch some rays and we will include a list of our favourite pieces of writing about Cuba - by writers including Hemmingway, Martha Gellhorn and Graham Greene - so you can get stuck into a paperback with your beachside mojito. Head back into town after sundowners for your final Cuban dinner.

Day 10: International Flight

Early this afternoon you will be privately transferred back to Havana in good time for your flight home.

All of the holidays we create are completely tailor-made to you

This sample itinerary is intended to give you a flavour of what we can do

A Rough Idea of Price

While all of our holidays are completely tailor-made and prices will vary based on things like time of year and level of accommodation, we want to give you as good an idea of how much this itinerary will cost. All of the costs on our sample itineraries exclude international flights, however, ask us if you would like us to arrange your flights at our preferred rates. The below prices are based on two people sharing.

This Itinerary

If you would like to book the exact itinerary mentioned above, during mid-season and staying in our preferred room category at our preferred hotels. Ask us if you would also like us to arrange your international flights.



Bare Necessities

If you would like to pare back the above itinerary by travelling at non-peak times, staying in a standard room and removing some or all of the guided activities.



Bells & Whistles

If you are looking for something extra special and would like to stay in top room categories at some of the most luxurious hotels we work with, and add more activities and guiding.



Ollie is our expert for this itinerary and, as a seasoned traveller, has the inside track on the most memorable adventures.

Call us on 1-866-205-8369