Private Journeys

Signature Cuba: The best of the highlights

14 days from £2,476pp



map marker Map

Day 1

Arrive in Havana. Transfer to hotel in the historic centre.

Private transport to your atmospheric hotel in the lively historic centre of Havana. 

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Day 2

Guided walking tour of Old Havana. Evening meal at a Cuban family home.

Your introduction to the city is a guided walking tour of Old Havana. The streets of La Habana Vieja were declared a UNESCO World Heritage Site in 1982, and the subsequent restoration of this part of town has transformed it into arguably Latin America's finest colonial quarter, in marked contrast to the rambling, potholed streets and crumbling façades around it. 

Stroll along the cobbles, between grand, pastel-hued mansions and bustling street life; music seeps out of every doorway and the narrow streets are clogged with gargantuan, crumbling 1950s American cars, which you will have the option of hopping into and cruising down the Malecón. You'll have trouble keeping your camera by your side as iconic images flash before you round each and every corner.

Enjoy a home-cooked dinner in a typical Cuban home (paladar). Afterwards, if you like, you might choose to visit vibrant Café Taberna in Old Havana for music and dance  epitomising the nostalgia and lively Caribbean spirit of Cuba. On arrival, enjoy a welcome cocktail to kick start your night as the music gets underway, calling to mind the 1950s and featuring one-time resident mambo king Beny Moré. Talented dancers exuding charisma and flair will accompany the band to complete a quintessentially Cuban scene.

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Day 3

By road to Viñales, western Cuba. 2 nights.

Continue by road to Viñales, a small, bucolic town tucked away in the Sierra de los Órganos. The shady high street is lined with trees, wooden colonnades and one-storey, red-roofed houses. Horse and carts clatter along the main road and local children play baseball with sticks and stones outside the dilapidated whitewashed church in the main square. There is a splendid old chemist's shop and a few other bare-shelved stores, as well as a couple of salsa bars that attract a lively crowd in the evening.

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Day 4

Half day guided walking in Viñales Valley.

The valley has a distinctive landscape, with dramatic limestone mountains, known as mogotes, which jut into the sky from a lush, fertile plain. Using oxen and carts, local farmers cultivate the red soil of the valley floor for fruit, vegetables and tobacco, and the countryside is peppered with thatched curing barns for drying the tobacco leaves. Included is a 9KM walk through this beautiful valley; the trail passes alongside fields being tilled by straw-hatted farmers driving their oxen, and you may have the opportunity to visit members of a campesino family in their home, where they'll brew you up a coffee, roll a cigar and talk to you about life on the land.

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Day 5

Transfer to rural Las Terrazas. 2 nights.

Travel on by land to visit the community project of Las Terrazas in the Sierra del Rosario UNESCO biosphere reserve. This is Cuba's premier centre for ecotourism, which offers the opportunity to get close to the local community, who coexist harmoniously with their surroundings. Stay at the much admired La Moka Eco-resort.

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Day 6

At leisure in forested countryside.

At leisure at Las Terrazas. Sierra del Rosario Biosphere Reserve sits on an impressive mountain range of tropical and semi-deciduous forest within the coffee-producing region of Pinar del Rio. The reserve is rich in flora and fauna and offers some the island's best bird-watching. Other notable wildlife includes bats, frogs and lizards. You have time to choose between optional activities such as hiking the trails, swimming under the waterfalls, bird watching or visiting an orchid farm or old coffee plantation.

Day 7

By road to Cienfuegos port, Pearl of the South. Overnight.

Today you head through the central heartland of Cuba, a transition between the pre-Revolutionary prosperous western plantations and the cattle pasture of the poorer east.  The elegant city of Cienfuegos is an important port town founded by French settlers from Louisiana in 1819. Its French founders left their mark in broad neoclassical boulevards, art deco façades and blond inhabitants but there’s also a strong Afro-Caribbean presence. This is a seafaring city with salt in the air; it’s the world’s primary sugar port. The ambience and architectural style is distinct from that of the rest of the island. 

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Day 8

Guided walking city tour. By road to colonial Trinidad. 2 nights.

You have a walking tour of this easy-going place, identified by the sobriquet the ‘Pearl of the South’, so very different from the other cities in Cuba. Later drive on to the city of Trinidad.

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Day 9

Guided tour of the city and Sugar Mill Valley.

Trinidad was declared a UNESCO World Heritage Site in 1988. Its popularity has not affected its colonial charm and unhurried atmosphere. Low-rise, brightly painted houses with vast shutters open out onto cobbled streets, palm trees dot the main plaza and evening entertainment continues into the early hours with dancing and music each night.

You’ll have a guided tour of the city and venture into the surrounding countryside, the Valle de los Ingenios (valley of sugar mills). In the 18th and 19th centuries, this region was one of the wealthiest as a result of its participation in the sugar boom. Visit the Manaca-Iznaga tower, climb to the top and enjoy some of the best views in Cuba. From here, the plantation owner kept a watchful eye on the slaves working in the fields below. The views across the valleys of sugar cane fields are breathtaking in the late afternoon light.

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Day 10

By road to Santa Clara, guided city tour, continue to island Cayo Santa María

Continue by road to Santa Clara (2 hrs). Half a century ago the capture of the railway here, by Che Guevara assisted by just 18 guerrillas, was instrumental in the triumph of the Revolution. Today, this vibrant university town is home to an excellent museum dedicated to the events of the late 1950s and to Che Guevara. There’s a guided tour with time to visit the armoured train ambushed by Che Guevara’s revolutionaries, Che's mausoleum and a monument and plaza dedicated to the man and the Revolution.

Continue by road to the beautiful Caribbean beaches of Cayo Santa Maria.


Days 11-12

At leisure on the beach.

Transfer to Cayo Santa María, one of a string of small tropical coral cayes (they form part of the Jardins del Rey archipelago) connected to the town of Caibarién on the mainland by a 48km causeway. The little island (2 x 13km) is blessed with gorgeous powdery white sand beaches, mangroves and calm turquoise waters, ideal for snorkelling and diving. The eponymous national park has interesting wildlife, especially birds and reptiles. The island is served solely by a small cluster of resort hotels and has no real local village life. This is your beach time, relax on the sand or take part in water sports organised from your all-inclusive hotel.


Days 13

Transfer to Las Brujas and continue to Havana overland. Overnight.

Transfer by road from Cayo Las Brujas overland to Havana.

Day 14

Transfer to airport for international flight home.

Inspired by this trip

Our exciting range of articles on Latin America explore everything from iconic destinations and lesser-known cultural gems to delicious traditional recipes. You’ll also find exclusive travel tips, first-hand client reviews and the chance to get your personal questions answered by our travel experts.


Your edit for Latin American inspiration

Our exciting range of articles on Latin America explore everything from iconic destinations and lesser-known cultural gems to delicious traditional recipes. You’ll also find exclusive travel tips, first-hand client reviews and the chance to get your personal questions answered by our travel experts.

View Extraordinary Inspiration

Real Latin America Experts

  • Carrie Gallagher
    Carrie Gallagher - Travel Consultant

    A former JLA tour leader, Carrie brings a wealth of on-the-ground experience to our London-based Escorted Groups team.

  • Lina Fuller
    Lina Fuller - Travel Consultant

    Lina's passion for the continent where she was born really took off when she moved to Córdoba to study, spending the holidays travelling between Argentina and her native Colombia.

  • Paul Winrow Giffen
    Paul Winrow-Giffin - Travel Consultant

    After graduating in Computer Science, Paul spent seven months travelling from Colombia to Argentina and came home hooked on Latin America.

  • Evie Oswald
    Evie Oswald - Travel Consultant

    It’s hard to believe that Evie has had time to cram so much in to her life so far. Having lived as a child in the Americas and Europe she found herself immediately attracted to Latin America.

  • Mary Anne Nelson
    Mary Anne Nelson - Travel Consultant

    Born in the Atacama Desert in northern Chile, Mary’s insider knowledge and dry sense of humour make her a highly valued member of the Tailor-made team.

  • Hannah Donaldson
    Hannah Donaldson - Travel Consultant

    Having spent part of her childhood in Colombia and worked in Brazil and Costa Rica, Hannah's ties to Latin America run deep. Hannah is an invaluable part of our Group Tours team.

Meet the team