Cross Island Adventure Tour

Arrive in Havana, where your private driver will meet you at the airport and transfer you to your accommodation. Once refreshed, set out with a local guide to discover the historic streets, plazas and colourful façades of Habana Vieja. Ease into the rhythm of the city over freshly prepared mojitos accompanied by live Cuban music before sitting down to dinner inside the celebrated Fábrica de Arte Cubano. Afterwards, explore this multifaceted cultural venue privately, moving between galleries, performances, DJs and creative spaces for an energetic introduction to contemporary Havana.

Spend the day exploring Havana through its art, architecture and unmistakable street life. Begin at the Museo Nacional de Bellas Artes, home to an extensive collection tracing the development of Cuban artistic expression. Continue to the magnificent Gran Teatro de La Habana before pausing for lunch at a local paladar. Later, climb into a vintage American convertible and cruise through Havana’s distinctive neighbourhoods, experiencing the city from one of its most iconic forms of transport. Your evening concludes over dinner in an atmospheric restaurant that reflects the architectural elegance and character of the Cuban capital.

Delve deeper into several traditions closely associated with Cuba. Visit a local cigar factory to see the craftsmanship behind the country’s internationally renowned tobacco industry before continuing through Havana’s historic landmarks. After lunch and a strong cafecito, travel to Finca Vigía, Ernest Hemingway’s former Cuban home, preserved much as it was during the decades he lived on the island. Later, trade literary history for movement during a private salsa lesson with an experienced local instructor. End the day with dinner at a restaurant led by one of Cuba’s recognised chefs, bringing another flavour of Havana’s contemporary dining scene into the journey.

Leave Havana after breakfast with your private driver and guide, travelling towards Cuba’s southern coast and the elegant city of Cienfuegos. Pause for lunch overlooking the sea before exploring a historic centre shaped by distinctive French architectural influences and a relaxed Caribbean setting. Continue east towards Trinidad, one of Cuba’s oldest and most evocative colonial towns, where cobbled streets and colourful historic buildings create an atmosphere seemingly removed from modern life. On arrival, settle into your accommodation and enjoy a relaxed dinner, marking the beginning of your stay in this beautifully preserved corner of the island.

Head into the lush countryside surrounding Trinidad for a day combining nature, agriculture and local traditions. Follow walking trails through the region before visiting a coffee farm to learn how beans are planted, cultivated, harvested and roasted, finishing with a taste of freshly prepared Cuban coffee and lunch. Back in Trinidad, step inside a local gallery for a more personal encounter with the town’s artistic community and the opportunity to meet a practising artist. In the evening, experience another side of Cuban life over dinner and music in a local home, centred on conversation, hospitality and shared traditions.

Depart Trinidad and travel north to Santa Clara, a city closely associated with the history of the Cuban Revolution. Pause for a traditional lunch accompanied by cafecito and a mojito before visiting the Che Guevara Memorial and mausoleum. Continue experiencing the city through its contemporary cultural life with live music performed by a local musician. Later, travel onwards towards the beaches of Cayo Santa María, where the pace changes dramatically from Cuba’s historic cities to the Caribbean coast. Settle into your accommodation and enjoy dinner onsite, with the next two days devoted to this quieter seaside setting.

Travel from Cayo Santa María to the historic Marcelo Salado Sugar Museum, where the remains of a former sugar complex provide insight into an industry that profoundly shaped Cuba’s economy and society. Continue the experience aboard an old steam locomotive bound for the colonial town of Remedios, evoking an earlier era of Cuban rail travel. Afterwards, return to Cayo Santa María for lunch and a relaxed afternoon beside the Caribbean. Spend time enjoying the island’s beaches and interacting with the local community before returning to your accommodation for an unhurried dinner.

Enjoy a slower day dedicated to the natural beauty of Cayo Santa María. The morning is free to relax and make the most of the island setting before an easy lunch at your accommodation. Spend the afternoon along the cay’s white-sand beaches, with warm Caribbean waters and an altogether gentler pace after several days of cultural exploration across the island. The evening brings the group together once again for dinner in Santa María, offering time to reflect on the journey so far before travelling back towards Cuba’s colonial heartland the following morning.

Leave Cayo Santa María after breakfast and return to Remedios for a more detailed exploration of one of Cuba’s lesser-visited colonial towns. Walk around its restored historic buildings and central plaza while learning about local traditions, including the elaborate annual festivities for which the town is particularly known. Pause for lunch at a neighbourhood restaurant before beginning the journey west to Havana. After checking into your accommodation, the evening is intentionally left free, allowing you to revisit a favourite corner of the capital, discover somewhere new or simply enjoy a relaxed final night in Cuba at your own pace.

Enjoy your final morning in Havana before checking out and meeting your driver for the private transfer to the airport. Your cross-island journey concludes after connecting several distinct sides of Cuba — from Havana’s art, music and historic neighbourhoods to the colonial architecture of Cienfuegos and Trinidad, the revolutionary heritage of Santa Clara, Cuba’s sugar-growing history around Remedios and the Caribbean shores of Cayo Santa María. Continue to the airport for your onward flight, bringing ten days of cultural encounters, landscapes and local experiences to a close.