Bespoke Cuban Holidays for the Discerning Traveller

7 Days in Cuba + 7 Days in Caribbean

A tailored 14-day itinerary can be organised by Esencia to give you the best of both worlds: a trip to Cuba, the largest and most diverse island in the Caribbean, and an opportunity to explore some beautiful and idyllic locales surrounding it. With your own personal Esencia chauffeur to guide you, you could spend a few days in Cuba’s exuberant capital, Havana, then venture out to historic Trinidad, the Valley of the Sugar Mills, and the Bay of Pigs. You’ll indulge in mouth-watering Cuban delicacies and swim in crystal, coral-rich waters. Then, for the last seven days of your trip, you can even get to choose one of Esencia’s specially selected luxury destinations in the Caribbean to make your holiday truly unforgettable.

Continue reading below to know how Esencia can organise a bespoke tour of Cuba and the Caribbean for you:

Day 1

On arrival in Havana, you will be met by Esencia’s chauffeur who will drive you to your luxe hotel or private B&B either in the historic Spanish Colonial Old Town, on the Malecón ocean road, or in the heart of the hip, leafy, Vedado district. Choose from the resplendent, intimate 19th-century Hotel Isabel; the handsome, evergreen Hotel Saratoga with its rooftop pool and outstanding city views; the sleek, botanical-themed modern Hotel Terral with its ocean-facing penthouses, or 1950s Vedado B&Bs replete with the works of avant-garde artists.

Day 2

A guided walking tour of Havana’s UNESCO World Heritage Site Old Town will reveal the architectural jewels built by the conquering Spaniards between the 16th and 19th century — the cobblestone plazas bulging with bougainvillea, the stunning porticoed mansions, and Cuban baroque churches. Visit museums and quirky shops buried in the narrow, cobblestone streets before breaking for coffee and cake at El Escorial on the restored Plaza Vieja. Indulge in a full seafood lunch at El Templete by the port, or a quick lunch at private tavern El Chanchullero.

After lunch, head across Havana’s harbour to visit the magnificent monumental forts of El Morro and La Cabaña before crossing town to visit the vast, iconic Plaza de la Revolución, and the luxe mansions turned embassies of the Miramar district.

Day 3

Explore the hip, residential neighbourhood of Vedado with its smattering of museums (the Museum of Decorative Arts, the Napoleonic Museum), art galleries (Galería Habana, Galería Servando Cabrera and Galería Villa Manuela), and the marble mausoleums of the Christopher Columbus cemetery. Spend the evening feasting on Havana’s new wave of cuisine at one of the district’s hip new private restaurants.

Day 4

Your chauffeur will drive you to the remote Bay of Pigs, site of the historic battle in 1961. Located in the Zapata swamp in southern Matanzas province, Playa Girón is home to Cuban crocodiles and plentiful birds. Stay at hospitable B&B Casa Ronel, and visit the Playa Girón Museum, detailing the disastrous US-backed invasion of 1961.

Day 5

After snorkelling or diving in the coral-rich seas off Playa Girón, you will be driven to the UNESCO World Heritage Site of Trinidad with its wobbly cobblestone streets packed with plazas, mansions, and churches. Caliente by day and caliente by night, Trinidad boasts one of Cuba’s most active music scenes so salsa lovers can dance straight into the groove. Spend the night in the only hotel with pedigree, the Iberostar Grand Hotel.

Day 6

Venture into the sub-tropical forests behind Trinidad to bathe in the waterfalls and explore coffee plantations of the Topes de Collantes mountain resort; or, head out on a vintage steam train that puffs its way from Trinidad into the Valley of the Sugar Mills where ruined sugar plantations are scattered across the hills — the source of Trinidad’s wealth and architectural splendour.

Day 7

Return to Havana, pulling in at American novelist Ernest Hemingway’s home-turned-museum, Finca La Vigía, on the way. After touring his house and garden, head to his favourite seaside spot at Cojímar, just east of Havana.

Day 8-14

Fly to Cancún, Mexico, and relax, barefoot, at the gorgeous Hotel Esencia with its spa and cooking classes at Playa del Carmen in the Yúcatan. Alternatively, fly into Panama City before heading off on a small plane to the Hacienda del Mar on San José Island, a slice of eco luxury in the Pearl Islands sprinkled in the Bay of Panama. Or, check in for some über-relaxation with yoga, or painting classes at rustic-chic Jakes Hotel on Treasure Beach, Jamaica.


If you are interested in only visiting Cuba, we offer a bespoke 14-day tour of the country as well as a guide on exploring Cuba in 2 weeks.

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