This two-week trip introduces you to the history behind these Cuban icons.
When one thinks of Cuba – what comes to mind? Sultry nightclubs with salsa and merengue music pouring from the open windows, lively jazz clubs and tropical cabarets, and certainly the faded opulence of the old cities’ colonial façades. Beyond that of course: rum, cigars and revolution. Cuba’s revolutionary trajectory since its Independence from Spain in 1898 has played a huge part in global history – the tense days of the Cuban Missile Crisis having been one of the defining moments of the Cold War. For a country so shrouded in mystery – perhaps it is surprising that the products of this quirky island have been avidly consumed worldwide. This immersive two-week tour will introduce you to the people and stories behind these Cuban icons: visit the site of Bacardí’s first rum distillery, learn about traditional tobacco cultivation and cigar rolling in the pretty valleys of Viñales, and visit Santa Clara, where Che Guevara’s military successes made him into a global icon.
Explore colonial Havana, then enjoy a cigar-and-rum pairing experience with a local cigar sommelier.
Visit a traditional tobacco farm in Viñales and trek on horseback to meet the Miranda family for coffee, rum and cigar tastings.
Take a personalised city tour of Santiago de Cuba and learn about the island’s rum heritage at the Rum Museum.
Delve into Cuban revolutionary history with visits to the Moncada Barracks in Santiago and the Che Guevara Mausoleum in Santa Clara.
Ride on horseback through the Valley of the Sugar Mills, exploring historic plantations and learning about the region’s links to the slave trade.
Cuba can be visited any time of year because its warm tropical climate offers pleasant weather and vibrant cultural experiences year-round.
We just returned from our 10-day trip to Cuba. We really could not have asked for or expected more.
– Humboldt Client
Arrive into José Martí International Airport where you will be met by a guide and taken to your hotel by private transfer where you will spend three nights in the bustling city of Havana.
Explore colonial Havana with your guide this morning and learn more about the colourful history of this influential city’s role on the world stage. In the afternoon you will enjoy a cigar-sommelier experience at a local café where a Cuban cigar expert will pair specially selected aged-cigars with fine locally produced rums.
This morning, enjoy an illuminating culinary tour of local markets before spending the afternoon driving the streets of Havana in an open-topped classic American car. Your tour will focus on Cuba’s revolutionary history and your guide will explain the evolution of Cuba’s unique politics since the declaration of Independence from Spain.
Today you will leave Havana and drive into the countryside to Viñales. Upon arrival, enjoy a delicious local lunch and a tour of one of the traditional tobacco farms in the region, where cultivation methods have remained the same for centuries.
Enjoy a day of cultural immersion in Viñales. You will trek through the valley scenery on horseback with local guides to the farm of the Miranda family to learn about their tobacco, coffee and rum business – with an opportunity to sample all three! A home-cooked lunch will be included, and you will have time to relax with the family on this picturesque farm.
Early this morning you will transfer to the airport in Havana and you will board a local flight south to Santiago de Cuba where you will spend the next three nights.
The next day, your expert guide will take you on a revolution tour of Santiago. This city played a key role in the beginning of the Cuban Revolution led by Fidel Castro, with the storming of the Moncada Barracks proving to be a decisive turning point in Cuban history. The evening will be at your leisure.
Your guide will collect you this morning in Santiago and transfer you to Camaguey in time for a delicious local lunch. In the afternoon, you will explore the cobblestoned alleyways of this lesser visited UNESCO World Heritage town centre and spend a night in the city
Today you will set off for Trinidad, arriving for lunch and exploring the old town with your guide in the afternoon. You will spend the next two nights in this stunning colonial city.
Your full day tour today will take you into the Valley of the Sugar Mills. Enjoy trekking on horseback through these green valleys where sugar plantations once reigned supreme. Your guide will offer illuminating insights into the dark history of this region’s relationship with the slave trade as you explore the ruined plantation buildings and the crumbling mansions of the 19th century sugar barons.
Today you will transfer to the student-city of Santa Clara, a city long at the centre of Cuba’s intellectual culture and revolutionary fervour. You will check in to your boutique hotel for the next two nights and have the rest of the day at leisure.
This morning you will return to Havana to spend one final night in the city. Your concierge can assist you with organising tickets to evening music and dance shows, as well as recommend the best places for your final Cuban meal!
We offer a truly personalised service providing a more authentic, caring experience. As a family-run business, we like to treat our guests like an extended part of our family rather than just clients.
Our team have visited and experienced every region we sell. We design your holiday using this first-hand knowledge, ensuring you have the benefit of our specialist’s depth of experience.
We believe that luxury travel can be a force for good, creating transformative experiences that give back; enriching lives, uplifting local economies, and preserving the planet’s most precious places.
At Humboldt we go the extra mile and pay attention to the smaller details so that your trip is individually crafted with care.
Independent Service Rating based on 296 verified reviews.
1 June 2026
17 April 2026
Lisa Z
16 April 2026
14 March 2026
Rob Masson
6 March 2026
Paul Edmondson
27 February 2026
Siwan Jones
11 February 2026
9 February 2026
John and Katie Wilkinson
26 January 2026
Pam Cowan
22 January 2026
22 January 2026
Get in touch with us and one of our travel experts will answer any questions you may have and help create your dream trip.