Bespoke Cuban Holidays for the Discerning Traveller

14 Day Tour of Cuba

There’s no better way to explore Cuba than with Esencia’s luxury 14-day Cuban adventure. This bespoke blend of insightful guided tours, luxury accommodation, mouth-watering cuisine and hot salsa beats is like nothing else you’ll ever experience. Starting off in Cuba’s culturally rich capital, Havana, you’re chauffeur-driven to such beautiful, historic locales as Trinidad, Baracoa, Santa Clara and the Bay of Pigs. Your opportunities include exceptional museum tours, beautiful walks through valleys studded with picturesque limestone stumps, snorkelling in crystal blue coral seas — even a private salsa class. Put simply, Esencia’s bespoke 14-day tour of Cuba is an unparalleled holiday experience in the beating heart of the Caribbean, replete with the very best that the island has to offer. Here’s a sample itinerary of what a tailored tour of Cuba we can organise for you:


Day 1

On arrival in Havana, you will be met by Esencia’s chauffeur who will drive you to your colonial chic hotel, or authentic B&B, either in the Spanish colonial Old Town, on Havana’s wind-swept ocean road, the Malecón, or in the heart of the leafy streets of the Vedado district. Choose from the glorious colonial relic, the 19th-century Hotel Isabel; the handsome, high-octane Saratoga with its alfresco rooftop pool; the petite, botanical-themed modern Hotel Terral with its ocean-facing penthouse suites, or 1950s Vedado homes replete with the works of avant-garde artists.

Day 2

A guided walking tour of Havana’s UNESCO World Heritage Site Old Town will take you past cobblestone plazas bulging with bougainvillea, stunning porticoed mansions, Cuban baroque churches, and handsome villas turned museums, all built by the conquering Spaniards between the 16th and 19th century. After lunch at private restaurant Doña Eutimia, buried in an alley close to the cathedral, or smart portside fish restaurant El Templete, tour the home studios of Cuba’s leading and emerging artists gaining insight into the thriving Cuban arts scene. At sunset, cruise the ocean road in a convertible American classic car (Yank Tank), admiring the sunset glow on the crumbling buildings that face the sea.

Day 3

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

Day 4

After snorkelling or diving in the stunning blue waters off Playa Girón, you will be driven to the UNESCO World Heritage Site of Trinidad, a tiny time-warped Spanish colonial town of plazas, mansions, and churches. Its balmy nights lure music lovers out on the town to enjoy one of Cuba’s most active live music and salsa scenes. Spend the night in the quiet rooms of the centrally located Iberostar Grand Hotel.

Day 5

Venture into the sub-tropical forests behind Trinidad to explore the waterfalls and coffee plantations of the Topes de Collantes mountain resort or, board an antique steam train that puffs its way out of 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 6

Recline on the soft sands of Ancón beach, just 13 kilometres south of Trinidad, and sail out to Cayo Blanco for a spot of snorkelling in the coral seas. In the afternoon, tune into Cuba’s musical rhythms by learning to play the drums, and other pivotal percussion instruments — the clave, and the güiro — before moving on to some choreographed footwork in a private salsa class.

Day 7

Return to Havana via the urbane university city of Santa Clara, home to the mausoleum of Revolution hero Che Guevara, a pretty central plaza, and the city’s gay and alternative club, El Mejunje.

Day 8

From Havana, fly direct to Baracoa, Cuba’s best-kept secret. Pitched between the Bay of Honey and the Bay of Porto Santo, facing the wild Atlantic on Cuba’s far eastern coast, is the tiny, quirky city of Baracoa. The first city founded by the conquering Spaniards, it basks in tropical light, and is surrounded by crystalline rivers, coconut palms, coffee plantations and cocoa trees.

Day 9

Head up Baracoa’s flat-topped mountain, El Yunque, for remarkable views of this fertile corner of Cuba, then relax by boating down the River Toa flanked by swaying palms. Spend the afternoon visiting the church, city museum and archaeological museum, before grazing your way around Baracoa’s culinary delights — from meaty stews cooked in coconut milk to hot chocolate, coconut candies, and earthy, herb-infused drinks.

Day 10

Head overland to Santiago de Cuba, the island’s second city. Santiago thrums to the sound of melodic music and dance and it’s here you’ll want to shimmy to salsa and son at the city’s venerable music houses — the Casa de la Trova, Artex and Casa de las Tradiciones. Visit the oldest house in Cuba, the Moorish-influenced mansion of the island’s first Spanish governor, Diego de Velázquez.

Day 11

Rise early to reach Santo Domingo village, buried deep in the lofty Sierra Maestra mountains. A moderate trek of a few hours will bring you to Fidel Castro’s former HQ during the 1956-59 rebel campaign. Sleep deeply overnight in the new alpinesque cabañas of the Villa Santo Domingo.

Day 12

Head to the north coast to zone out in tropical luxury at the Paradisus Río de Oro resort on the golden curve of Playa Esmeralda at Guardalavaca, north of Holguín.

Day 13

Loll in the spa or lounge about in the boats at the Paradisus Río de Oro.

Day 14

Return to Havana by plane.


Our guide to exploring Cuba in two weeks provides you with the must visit tourist spots across the country. If you are looking to experience the Caribbean, as well as Cuba, take a look at our 7 days in Cuba and 7 days in the Caribbean holidays.

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