Contents
Why 1953? That was the year the Cuban Revolution began, and for a long time afterwards the embargo kept the island looking like a place the twentieth century had not finished with. No American chains, very little outdoor advertising, and a street of old American cars that were still working because new ones could not come in. A lot of that surface is still there. The practical layer underneath it is not.

This is the arrival. The old city is the next morning, in the Havana walking tour. Miramar, Revolution Square, and the Malecón at sunset are the afternoon, in Driving in Miramar and along the Malecón. Viñales is the day out of town, in the Viñales Valley day. The rest of the Cuba notes sit in the Cuba archives.
What has changed since I landed
I flew in from Los Angeles through Cancún, on a short hop that felt older than the airport I had left. A woman in the first row knew the crew, talked through taxi and takeoff, and was still on her phone when I was already wondering how I would get online. At the time, roaming did not behave, the hotel lobby sold an hour of Wi-Fi, and I decided to stay off the grid.
That decision is harder to make now, and less romantic. Cuba’s phone and public Wi-Fi still run through ETECSA. You buy a Nauta card for the hotspots, or a Cubacel tourist SIM if you want data on your own phone, and the power grid can still take the network down for an afternoon. Hotel Wi-Fi is no longer a rare favour. It is also not the connection you are used to. Download the maps before you fly.
Money is the bigger change. When I visited, Cuba was running two currencies: CUP for local life, and CUC, the convertible peso, for hotels, taxis, and anyone who looked like a tourist. One CUC was pegged near one US dollar, and a taxi driver could earn in a week what a civil servant earned in a month. That dual system ended in 2021. CUC is gone. The peso is CUP, the official rate and the street rate are not the same thing, and the street rate moves. In 2026 it has been hundreds of CUP to a dollar. Do not travel on a blog’s exchange rate. Check the week you go, carry cash, and do not assume a foreign Visa or Mastercard will work at the till. Card acceptance has been switched off before.

The pink tourist card I would have told you to buy at the airport is also gone for most air arrivals. From 2025, air travellers have been moved onto an e-Visa, applied for before the flight, with a longer stay than the old 30-day card. If your itinerary starts in the United States and flies straight to Cuba, the airline may still be the one that issues the entry document. Confirm on the official Cuban visa page for your nationality before you book. This is the fact that goes stale first.
Flights move too. I connected through Cancún because that was the West Coast route. Direct services from Miami and other US cities have opened and closed with the politics. Toronto and Mexico City are the steadier connections. Do not plan on a sentence that says “20 direct flights.” Check the week you fly.
The landing

The cabin was old and dusty, and the flight from Cancún was only an hour. Once we were up, there were two juices in the trolley, both labelled Product de Cuba. I took the pear. It was thick and too sweet, and it was the first thing that told me I had left the airport logic of the mainland.
José Martí was the second. The hall was packed, the queues did not move, and it took close to two hours to get the bag and the pesos. By 9 p.m. I was tired and hungry, and halfway to the taxi rank an older man took the trolley and said “Taxi?” before I had agreed to anything. I followed him into a dark corner of the car park and found a vintage cab. I did not know how to open the door. There was no belt worth using. The engine sounded like a different decade, and for the first time the old American car was not a photograph. It was the transport.
The driver talked, in the English we both had, from local tips to the news. This was 2015. He knew about the Sony hack and the occupation in Hong Kong. I remember being surprised that a man driving a car from the 1950s was more current than the connection on my phone. That conversation belongs to the year I landed. It is not a guide to what the radio is saying now.

Where I stayed
I stayed at the Mercure Sevilla La Habana, a European-style house with a rooftop, a terrace bar, and a pool, a few blocks from the Capitol, Old Havana, and the Malecón. The dome of the Capitol sat outside the window. In the morning I opened it, turned on CNN, and watched the old buildings and the old cars go past underneath.
At the time, Havana hotels were a thin list on Cuban booking sites, ten or twenty properties, and the international sites were unreliable. That has loosened. The same houses now show up on the big booking sites, and the price is not the price I paid. Book the house, then read the latest note on cards and cash, because a confirmation is not the same thing as a working payment.
The Capitol view, the rooftop, and the walk into the old city the next morning are why I would stay in that pocket again. The four plazas are the walking tour. The drive west, and the sunset on the sea wall, are the Miramar afternoon.

The cars
When the break with the United States cut off parts and new models, the American cars already on the island stayed. They were mended, repainted, and kept in service, which is why a 1950s Chevrolet can still be the taxi that collects you at night.
The Miramar drive was arranged by a friend who guides: Quinta Avenida, the green streets, Revolution Square, then back to the Malecón. I was offered the wheel and turned it down. I do not drive a stick, and I did not want that particular car to be the one I learnt on.
The cars are the photograph. The plazas are the city. Start with the arrival if you are still deciding whether the island is a trip or a costume. Then walk.
Where to go next
The next morning is Old Havana on foot. Four plazas, Calle Obispo, the cathedral, the flea market at Plaza de Armas, and the Hemingway bars if you want the postcard after the buildings. That walk is written up in the Havana walking tour. I met the guide at Hotel Telégrafo, ten minutes early, and it turned out to be a private tour rather than the group I had expected. The Capitol dome I had been looking at from the hotel window is the landmark you start from.
The afternoon leaves the old city. Lunch at Café Laurent, a paladar with a roof over Vedado, then a vintage car through Miramar on Quinta Avenida, Revolution Square and the José Martí memorial, a drink at the Hotel Nacional, and the Malecón when the light goes. That sequence is in Driving in Miramar and along the Malecón. The sea wall is about eight kilometres. You do not need to walk all of it. You need the hour when the Morro is still visible and the city is behind you.
If you have a second day, leave Havana. Viñales is the valley of mogotes and tobacco, and the vintage-car ride out of town is the Viñales Valley day. Do not try to staple it onto the plaza morning.
What the island has been doing since 1953
The year in the title is the start of the revolution, not a costume party. After 1959, the break with the United States cut off the cars, the parts, and the brands, which is why the street can still look paused. The Soviet years kept the lights on. When that support went, the 1990s were thin, and tourism was opened in 1994 because the country needed the foreign cash. Private restaurants and houses followed in the 2010s. That is the Havana I landed in: a revolutionary state with a paladar on the roof and a 1950s Chevrolet still earning a living.
The last decade loosened the picture and then tightened it again. The US opening under Obama put commercial flights and a little more contact on the map. Later politics took some of that back. The dual currency I used, CUC for tourists and CUP for everyone else, was abolished in 2021. One peso was supposed to simplify life. Inflation did the opposite. Official and street rates diverged, cash became the sensible way to pay, and a foreign card is no longer something you can count on at the till. The pink tourist card of my visit has been replaced, for most air arrivals, by an e-Visa you arrange before you fly. None of that erases the Malecón. It does mean the island you book now is not the island I queued in.
What has not moved is the reason to walk it. Old Havana is still the plazas and the cathedral quarter. Vedado and Miramar are still the afternoon drive, Revolution Square, the Hotel Nacional, and the sea wall at sunset. Viñales is still the day the city lets you go. Continue on the journey with my Havana walking tour for the four plazas, then Miramar and the Malecón for the car and the sunset. If the week has a second shape, it is the Viñales Valley.
The rest of the notes are in the Cuba archives.




8 comments