Havana to Santiago the slow way, about 1,200 km of it — an urban farm in a housing estate east of the capital, tobacco vegas under the limestone of Viñales, the Bay of Pigs told from the side that won, the sugar valley above Trinidad, the armoured train at Santa Clara, and the shrine at El Cobre where the copper miners argued themselves out of slavery in 1800.
Havana, the old city
Change money before you do anything else and read the currency note below first, because getting this wrong on day one is expensive for a fortnight. Then walk the four plazas of Habana Vieja. The restoration you are looking at is unusual: from 1993 the Office of the City Historian, run until his death in 2020 by Eusebio Leal, was allowed to keep the hard currency its own hotels and restaurants earned and spend it on the district, which is why the core looks the way it does. Walk two streets west into Centro Habana and you see what the rest of the money has to cover. Buildings there come down, particularly after heavy rain, and people are killed in them most years — that is not a reason to avoid the neighbourhood, which is ordinary and busy and where most of the city actually lives, but it is why you look up.
Vedado and the Malecón
The twentieth-century city. Walk the Malecón west in the late afternoon, when the sea wall fills up and stays full; the Hotel Nacional on the bluff above it opened in 1930 and its garden still has the gun emplacements dug during the missile crisis. Then the Necrópolis de Colón, which is 57 hectares of marble and one of the largest cemeteries in the Americas, and the Plaza de la Revolución, where the Martí memorial faces the two ministry façades carrying Che and Camilo Cienfuegos in steel outline. Finish on the steps of the university. Coppelia still sells ice cream in pesos to a long queue and two flavours; the queue is the more interesting half.
Alamar and Cojímar
East through the harbour tunnel to Alamar, a housing estate of prefabricated blocks put up in the 1970s by microbrigades of workers seconded from their own factories to build their own flats. Something over a hundred thousand people live there, and it is where Cuban hip-hop started — the Alamar rap festival ran from 1995 and for a decade was the argument about what Cuban youth was allowed to say. On the edge of it is Organopónico Vivero Alamar, eleven-odd hectares of raised beds on ground that would otherwise grow nothing; arrange the visit a day ahead through your casa. Then down to Cojímar, the fishing village where Hemingway kept his boat and where a large share of the 1994 rafts were launched.
West to Viñales
Out along the Autopista and then the Carretera Central into Pinar del Río. Viñales sits in a flat-bottomed valley with mogotes standing out of it — limestone hills with vertical sides, what is left after the rest of the rock dissolved. UNESCO listed the valley in 1999 as a cultural landscape, meaning the inscription is about the farming: ox-drawn ploughs, small vegas, and the palm-thatched drying houses on the field edges. Walk up to the Los Jazmines viewpoint for the overview, then eat in town.
The valley and the tobacco
Walk or ride out through the Valle del Silencio, west of town, where the farms are and the coaches are not. Any grower will show you the casa de tabaco and explain the arithmetic that runs the industry: the state buys the leaf at a set price and takes ninety per cent of the crop, and the farmer keeps the remaining tenth to roll and sell himself, which is why a farmhouse cigar costs what it costs and why the man selling it is so keen. The Cueva del Indio is a short underground boat ride and is fine. The Mural de la Prehistoria, painted on a mogote face in 1961, is enormous and bad, and everybody goes.
The long day: Viñales to the Bay of Pigs
Around 380 km, six to seven hours, back past Havana on the Autopista Nacional and then south into Matanzas province. This is the transfer the route costs you and there is no clever way round it — a shared taxi arranged the day before is faster and more reliable than piecing it together on Viazul. You end at Playa Larga at the head of the Bahía de Cochinos, on the edge of the Ciénaga de Zapata, the largest wetland in the Caribbean and a biosphere reserve. The economy here is charcoal, fish and birds: the Zapata wren and Zapata rail live nowhere else, and the Cuban crocodile has one of the smallest ranges of any crocodilian on earth.
Girón, then Cienfuegos
Down the coast road with the swamp on one side and the sea on the other. Every few hundred metres there is a small concrete marker with a name on it, put where that militiaman was killed in April 1961. At Playa Girón the museum tells the invasion from the side that won — about 1,400 CIA-trained exiles landed, and the thing was over in seventy-two hours — and it is worth an hour whatever you think of the framing, because the artefacts are the ones the winners kept. Swim at the Cueva de los Peces, a flooded sinkhole across the road from the sea, or on the drop-off at Punta Perdiz. Then two hours east to Cienfuegos.
Cienfuegos, then over to Trinidad
The one Cuban city founded by the French — settlers from Louisiana and Bordeaux laid it out in 1819 on a grid, and its nineteenth-century centre went onto the UNESCO list in 2005 for exactly that neoclassical regularity. Walk the Prado down the peninsula to Punta Gorda, look at the Palacio de Valle of 1917, which is what happens when a sugar fortune cannot decide between Venice and Morocco, and put your head into the Teatro Tomás Terry of 1890. Then east to Trinidad in the afternoon, along the coast under the Escambray.
The Valley of the Sugar Mills
Trinidad was founded in 1514 and got rich late, on sugar, and then stopped — the town was inscribed by UNESCO in 1988 together with the valley that paid for it. Go out to the Valle de los Ingenios in the morning. At its height something like fifty mills worked here with more than thirty thousand enslaved people, and the seven-storey tower Alejo Iznaga built at Manaca in 1816 was put up to watch them in the cane. Climb it, then walk down through the ruins of the mill house. Back in town in the afternoon: the Museo Histórico in the Palacio Cantero, and the steps by the Plaza Mayor in the evening. Trinidad is the most touristed town in Cuba and the constant approach on the street is part of the deal here.
Santa Clara
Three hours north — the road runs east to Sancti Spíritus first and then up the Carretera Central, which is why a town almost due north of Trinidad takes as long as it does. Santa Clara is a university town and it behaves like one. The Tren Blindado monument marks the spot where, on 29 December 1958, a column under Che Guevara pulled up the rails with a bulldozer and derailed an armoured troop train; the bulldozer is there and so are four of the carriages. His remains, found in Bolivia and returned in 1997, are in the mausoleum on the west side of town, with a museum under it. In the evening go to El Mejunje, a roofless ruin of a courtyard that has been the town's cultural centre since 1985 and has run the oldest drag show in Cuba since the early 1990s — an institution that exists nowhere else on this route.
East to Camagüey
Five hours down the Carretera Central into the cattle country of the centre. Camagüey was founded on the coast in 1514 and moved inland in 1528, and its street plan is a knot rather than a grid — the local account is that it was built to confuse pirates, which is what Henry Morgan's sack of the town in 1668 is usually offered to explain, and historians mostly think it grew that way instead. UNESCO listed the centre in 2008. The symbol everywhere is the tinajón, the fat clay water jar the town made by the thousand because the water supply never worked. Camagüey also keeps the Ballet de Camagüey, founded in 1967 and still the country's second company after the Ballet Nacional in Havana.
To Santiago de Cuba
The second long haul: 330 km and about six hours, with the Sierra Maestra coming up on the right for the last of it. Santiago was the capital until 1589 and has never entirely accepted the demotion. It faces the wrong way for Havana and always has: French planters came over from Saint-Domingue after the Haitian revolution and their descendants still keep the tumba francesa drum-and-dance societies going, Haitian and Jamaican cane cutters were shipped in by the tens of thousands in the 1910s and 1920s, and the carnival in the third week of July is the one that matters. It is the city Havana is measured against by everyone who lives here. Do nothing on arrival except walk to Parque Céspedes and then to the Casa de la Trova, where son is played from the late afternoon onwards by people who have been doing it for fifty years.
Moncada, Santa Ifigenia, El Morro
The Moncada barracks, attacked on 26 July 1953 by about 130 people under Fidel Castro in an operation that failed completely and gave the movement its name and its date. Batista had the bullet holes plastered over; they were re-cut into the façade after 1959, which is worth knowing while you photograph them. It is a school now, with a museum in one wing. Then Santa Ifigenia cemetery: José Martí under an octagonal mausoleum lit from above, with the guard changed every half hour, Céspedes, Compay Segundo, and since December 2016 Fidel Castro under a single granite boulder with one word on it. In the late afternoon the Castillo de San Pedro de la Roca on the cliff at the harbour mouth — begun in 1638, UNESCO-listed in 1997, and the best-preserved Spanish coastal fortification in the Americas.
El Cobre, and out
Twenty kilometres north-west to the basilica of the Virgen de la Caridad del Cobre, declared Cuba's patron in 1916 and crowned by John Paul II in 1998, where the chapel of offerings is stacked with the things people have left — including the Nobel medal Hemingway won in 1954 and handed to the shrine rather than keep, dedicating it to the Cuban people. The hill behind it is the reason the village exists: copper was mined here from the 1530s by enslaved Africans, and the cobreros spent a century petitioning the Spanish crown over their status until a royal order in 1800 declared them free — one of the earliest such outcomes anywhere in the Americas, and won by argument rather than by rising. Then the airport. Read the note below about the flight before you rely on it.
Good to know
Entry is by e-Visa now: the paper tourist card has been superseded by an electronic visa bought at evisacuba.cu for roughly €22–25, and while some airlines still sell a card at check-in for a markup, buy the official one. Separately and free, everyone must file the D'Viajeros declaration at dviajeros.mitrans.gob.cu in the seven days before arrival and carry the QR code it produces. Travel medical insurance valid in Cuba is mandatory and is checked at the desk; policies issued by US insurers are generally not accepted, and if yours fails you buy a Cuban one at the airport. The consequence to understand before you book anything: travel to Cuba on or after 12 January 2021 permanently removes your eligibility for the US Visa Waiver Programme, so a future trip to the United States means a B1/B2 interview at a consulate rather than an ESTA, and it attaches to the trip regardless of your routing or whether Cuba stamped the passport. US citizens have a second layer — American law still prohibits tourism, travel has to sit inside one of twelve OFAC categories, in practice Support for the Cuban People, which requires a full-time schedule of qualifying activities and five years of records kept in case they are asked for, and the State Department publishes a Cuba Restricted List of hotels and entities Americans may not use. Money is the thing most trips get wrong. Currency unification began on 1 January 2021 and the convertible peso was out of circulation by the end of that year, leaving the Cuban peso as the only legal tender, but it has an official rate, a bank retail rate and an informal rate that have not agreed with each other in years, and the informal one is what the country actually trades at — check the daily figure elTOQUE publishes before you change anything, because the gap is the difference between a cheap fortnight and a very expensive one. No card issued by a US bank works anywhere in Cuba, on any network, and non-US Visa and Mastercard work erratically at best, so bring the entire trip in cash, in euros, in clean unmarked notes. Change with your casa owner or a business rather than on the street. Bring more than you think: there is no way to top up if you run out. Electricity is the other planning constraint. The grid has collapsed nationally more than once since October 2024 and rolling cuts of eight to twenty hours a day are routine outside central Havana — ask when booking whether the casa has a generator or a battery, carry a torch and a power bank, and expect a fan rather than air conditioning to be the thing that actually runs. Fuel shortages cancel Viazul departures at short notice; book at viazul.com in advance, but treat every long leg as provisional and keep the number of a colectivo driver, which is how Cubans move and how you will move on at least one of these days. The Santiago–Havana flight on the last day is the most fragile booking on this route and it is the reason the itinerary ends where it does: the domestic network is flown by Cubana and Aerogaviota on a small, ageing fleet, the same fuel shortage that cancels coaches grounds aircraft, and routes have been suspended for months at a time since 2023. Book it the moment you have dates, expect a cancellation rather than a delay if one comes, and know your fallback before you need it — Santiago to Havana by Viazul is a fifteen-hour overnight coach, and the national train is slower still and suspends without notice. Do not put an international departure the same day; leave a night in Havana between them. If the flight cannot be secured at all, take the nine-day western variant instead. Tap water is not drinkable anywhere on this route — bottled, boiled or filtered. Pharmacies are largely empty, so bring every medicine you might need including painkillers, rehydration salts and antibiotics if your doctor will prescribe them, and bring more than you need because leaving the surplus with your hosts is genuinely useful. Hurricane season runs 1 June to 30 November with the peak from August to October; Cuba's civil defence evacuation system is one of the most effective in the region and you should do exactly what you are told, but a storm still means several days with no transport and no power. Connectivity is ETECSA and only ETECSA — buy a tourist SIM or eSIM on arrival, and note that data prices rose steeply in 2025 and are high against Cuban wages, which is why people cluster in the park with the hotspot. Drones are confiscated at the airport without a permit obtained in advance. One more thing to have in your head before you arrive, because it is the subject that comes up unprompted in every casa on this route: the country is emptying. Cuba's own statistics office now puts the population under ten million, down from over eleven, and the people who have gone are overwhelmingly the working-age bracket that runs the casas, the paladares and the taxis. Almost every household you stay in has a son or a daughter in Madrid, Miami or Montevideo. Politics is a different matter and is not symmetrical — a Cuban carries the risk of that conversation and you do not, so let people set its limits themselves, and do not photograph or post anyone in a way they have not agreed to. Sleep in casas particulares rather than hotels: private room rental has been licensed since 1997, paladares have been legal since 1993 and the private companies legalised in 2021 now run most of the good ones, and this is the one decision that determines whether your money reaches a household or a ministry.
Shorter or longer?
Add three days at the far end. From Santiago it is 230 km east through Guantánamo and then over La Farola, a road that climbs into the Sierra del Purial and was only finished in the 1960s — before it, Baracoa was reachable by sea. The town was the first Spanish settlement in Cuba, founded in 1511, and it grows cacao, coconut and coffee in a wet green corner that looks nothing like the rest of the island.
Havana, Viñales, the Bay of Pigs, Cienfuegos and Trinidad, then back to Havana in about four hours on the Autopista. Cuts Santa Clara, Camagüey and Santiago — which removes both six-hour bus days and the domestic flight, and with them most of the route's risk of going wrong.