Bespoke Cuban Holidays for the Discerning Traveller

10-day Tour of Cuba

From rousing history and stunning scenery to culture, cocktails and cabaret, our 10-day tour of Cuba is an exhilarating mix of experiences as diverse as the island itself. Esencia organises an unforgettable 10-day Cuban adventure with a bespoke selection of guided tours, leisure activities and accommodation, and your own personal Esencia chauffeur to guide you on your journey. You can explore historic towns and verdant valleys; soak up the sun on talcum-white beaches; learn about Cuba’s natural and man-made landmarks and legendary tobacco and sugar industries; and treat your palate to authentic Cuban delicacies at the most sumptuous restaurants on the island.

Below you can find an example of what a luxury 10-day tour of Cuba might be:

Day 1

On arrival in Havana, you will be met by Esencia’s chauffeur who will drive you to your hotel, or chic B&B, either in the historic Old Town, on Havana’s serpentine ocean road, or in the heart of the hip, leafy, Vedado district. Choose from the resplendent, old-world charm of the 19th-century Hotel Isabel; the handsome, evergreen Hotel Saratoga with its rooftop pool and captivating 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 spread 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. After lunch at tiny, private restaurant Doña Eutimia, or smart 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 Malecón in a convertible American classic car (Yank Tank), admiring the sunset glow on the crumbling buildings facing the sea. After sundown, head to Swedish—Cuban paladar, Casa Miglis, for dinner, and enjoy a post-prandial cocktail at its boho bar. During the midnight hour, enjoy the glitzy, alfresco cabaret of the world-famous Tropicana or, for something more hedonistic, join local hipsters in the 1950s red-leather basement bar of the Teatro Bertolt Brecht, and its adjoining music venue, plugging in to various musical moods.

Day 3

Your chauffeur will drive you to the UNESCO World Heritage Site of Viñales, a fertile karst valley rolling with tobacco fields and studded with forest-bound giant limestone stumps. On the way, you will stop at the eco-resort of Las Terrazas, visiting artists’ studios and French coffee plantation ruins. Enjoy lunch at one of Cuba’s few authentic vegetarian restaurants, El Romero. At Viñales, check into the candy pink, hilltop Hotel Los Jazmines and sip sundowners by the pool luxuriating in the timeless rural scene.

Day 4

Mount a horse or opt for a guided walk through the royal palm-peppered valley learning about the curious limestone stumps (mogotes), the world famous tobacco industry, and the lush regional flowers and fruit. In the afternoon, visit a tobacco farm in the nearby Vuelta Abajo region, site of the world’s best earth for tobacco plant cultivation.

Day 5

An early start is needed for the long journey to historic Playa Girón and the Bay of Pigs on the southern, swamp-bound coast of Matanzas province. At Casa Ronel’s B&B, you’ll enjoy a comfortable night after a fresh seafood dinner and home-mixed cocktails.

Day 6

Snorkel or dive in the glistening Caribbean waters off Playa Girón before setting off for the beautifully preserved Spanish colonial town and UNESCO World Heritage Site of Trinidad. Your nights will be spent in the town’s only hotel with a plush quota, the five-star Iberostar Grand Hotel.

Day 7

A guided walking tour of beautiful, tiny Trinidad will introduce you to this time-trapped town built from the riches of the sugar and slave trade that flourished in the neighbouring Valley of the Sugar Mills. After lunch, relax on the white-sand curve of Ancón beach, or hike to the Salto del Caburní waterfall in the nearby tropical mountain resort of Topes de Collantes.

Day 8

After breakfast, drive through sugar plantations and small towns to Cuba’s premiere beach resort, Varadero, on the northern coast of the island. Check into the former mansion of the chemical magnate, Irénée du Pont, that sits, proudly and elegantly, on a bluff overlooking the turquoise sea below. Unwind on butter-soft sands that unfurl 21-kilometre along this beach-cloaked peninsula.

Day 9

After catching rays on the warm sands, try your hand at one of Varadero’s multiple activities and watersports from kitesurfing to sailing, and from diving and snorkelling to paragliding above the peninsula.

Day 10

Return to Havana in the afternoon and explore leafy, artsy Vedado, and the marble splendours of the dead at the Columbus cemetery.


If you are interested in a shorter stay in Cuba, take a look at our tailored 6-7 day tour of Havana.

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