Havana Beyond the Cliches
The natural starting point for your tailor-made Cuba holiday is Havana. You can fly direct to the capital with Virgin Atlantic twice a week from London Gatwick or via Amsterdam, Madrid and Paris with KLM, Iberia and Air France respectively.
Havana is the setting for the convergence of Cuba's extraordinarily rich colonial, African, American, Soviet and revolutionary history, which have defined the unique culture we now encounter in the 21st century. You can spend your days exploring the hidden corners of the magnificent old town with one of our brilliant guides, venturing further out to see first-hand how the city has grown and developed over time and enjoying live music in the evenings. Yes there are the cliched (but attractive) gleaming vintage US cars everywhere, but there are also dusty bookshops, experimental art workshops, old-time cafes and excellent museums waiting to be discovered too.
Whilst Havana has some iconic state-run hotels, most of these do not provide guests with good service, making them more apt for an afternoon drink and souvenir photos. Instead, many of our guests opt to stay at one of our preferred casas particulares homestays or at one of the small number of good foreign-owned hotels.
Heading out of Havana, you might choose to visit Viñales, either on a full day trip or more commonly on a two night stay. This is a picturesque and fertile valley characterised by timeless tobacco plantations, vivid limestone hills and mysterious caves with underground rivers. The pace of life is slow here and beautiful scenery abounds.
Cienfuegos: The Pearl of the South
The next port of call might be Cienfuegos, an elegant city adorned with spectacular neoclassical 19th century architecture painted in attractive pastel hues. Evocatively known as the 'Pearl of the South', Cienfuegos differs from Cuba's other world heritage centres in that it was the French and not the Spanish who settled this area and populated the city, lending it an historically Gallic flair. Some of the city's best casas particulares and some of its most striking buildings are clustered on the thin peninsula of Punta Gorda, from where you can enjoy mesemerising sunsets and sunrises.
There are several options for excursions from Cienfuegos. Our favourite takes you to Laguna Guanaroca, just outside the city, to see flamingos, pelicans, egrets, herons and cormorants in a beautiful mangrove-lined lagoon, backed by the shadowy outline of the distant Escambray Mountains. In the adjoining forest you can get close to land crabs, hummingbirds, trogons, turkey vultures and more. Other popular day trips can lead you to the renowned Botanical Gardens or the spectacular El Nicho Waterfall.
The Seductive Streets of Trinidad
After a night or two in Cienfuegos, the next logical step on your travels is Trinidad - quite rightly known as the 'Jewel of the Caribbean'. The UNESCO world heritage centre is perhaps the finest colonial centre in the Americas, with an extraordinary density of colourful low-rise houses and mansions from the era, wonderfully preserved and with no hint of modernity to disturb the perfection. There truly is a timeless feel to Trinidad.
In the warm glow of the afternoon sun, the city is particularly seductive and the night then brings one of Cuba's finest live music scenes, with an authenticity and charm that even Havana can't match. Excellent museums chart the city's history, slave trade, architectural development and post-revolutionary conflicts, whilst some of the country's best and most unique local artists are based here.
The most popular day trip from Trinidad takes you into the heart of the Sugar Mill Valley, from where the city's colonial wealth originated. Former mills, grand colonial houses and the old sugar train provide insights into this most productive and vital of industries, whilst the centrepiece of the valley is the Iznaka Tower, affording glorious views over the fertile land and distant mountains.
The nearby Topes de Collantes in the Escambray Mountains provide some wonderful hiking opportunities. One of our favourite places is Parque Guanayara, where the path leads you past towering palms, exotic trees and the thundering El Rocio waterfall to an idyllic natural pool in which you can refresh yourself. En-route you'll likely see hummingbirds, trogons, parrots and butterflies, whilst soaking in some glorious panoramic vistas. You might like to relax afterwards for a few hours on Playa Ancon, an attractive Caribbean beach just outside Trinidad. Whilst we don't rate the resorts there very highly, it is a nice place to unwind for a while.
Santa Clara's Revolutionary Heroes
From Trinidad you might return by road to Havana before flying home. En-route you will be well-served stopping to explore the city of Santa Clara with your guide to learn more about Che Guevara. The city is synonymous with the revolutionary war hero because it was here that he masterminded the derailment of the government's tren blindado and effectively ended the war, forcing Batista into hiding. You will visit the museum to this event, housed in the derailed carriages of the train and at the spot where it occurred, as well as Che's mausoleum and the small museum dedicated to his revolutionary life.
Idyllic Beach Resorts
The Havana-Viñales-Cienfuegos-Trinidad loop is usually completed over the course of ten days to two weeks, two or three days less without staying in either Viñales or Cienfuegos. You can easily extend your trip with a relaxing stay at one of our preferred beach resorts on the white sands of Varadero, some 140km from Havana, or perhaps instead at Cayo Santa Maria and Ensenachos. Other popular places to visit in Cuba include two of the other seven cities originally established by the Spanish in the 16th century: Santiago de Cuba and Baracoa.
Santiago: The Cradle of the Revolution
Santiago de Cuba's fame extends partly from its connections with two of Cuba's most internationally renowned citizens; revolutionary leader Fidel Castro (who is buried here) and Segundo Compay, legendary singer with the Buena Vista Social Club. The city is regarded as Cuba's next biggest cultural centre outside of Havana and was considered as the 'Cradle of the Revolutionary' - a legacy which continues today. We find a wealth of excellent colonial architectural gems and strong Afro-Caribbean influences.
Baracao by contrast is more relaxed and provincial, inviting visitors to get off the main tourist trail, slacken their pace and savour intimate insights into a more traditional Cuban way of life, more associated with indigenous people than the rest of the island. There are a huge number of archaeological sights from pre-Hispanic times and the surrounding countryside is some of the most idyllic and timeless in all of Cuba.
Ready to plan your tailor-made Cuba holiday? We hope we have given you some food for thought here and opened up a few possibilities for you to consider. The next step is to discuss your ideas with one of our Travel Consultants who have travelled extensively here and ask them any questions you might have to help us plan an itinerary tailored to you and your interests and preferences. You might also like to browse some of our existing Cuba holidays below for inspiration, all of these can be tweaked or expanded to better suit you.
Suggested Itineraries View All
The Sombrero Tour
12 Nights from £2,532€2,012$2,545
Cuba projects a surreal mise-en-scene of classic cars, cyclists and derelict buildings, standing next to pristine, beautifully renovated colonial squares with cafes
The Havana City Tour
8 Nights from £1,797€1,167$1,516
Explore the fascinating and surreal city of Havana. Enjoy the Caribbean climate and relaxed pace of life, while learning about Cuba's dramatic history and its unique society
The Escambray Tour
12 Nights from £2,629€2,123$2,681
Explore Cuba's rich culture and history, admiring the colonial facades in Havana and Trinidad. And relax on a white sandy Caribbean beach
The Colonial Cuba & Exotic Nature Tour
0 Nights from Please EnquirePlease EnquirePlease Enquire
Experience Cuba's unique society in its attractive and atmospheric colonial cities. In the countryside discover thunderous waterfalls, idyllic natural pools, flamingo-specked…