Travel is all to do with doors: exploring what lies beyond them. For journeys in Latin America, though, the Spanish word puerta is a better term: it covers a multitude of openings, from the creaky old door of the Hotel Caribbean in the Cuban capital, to the Gate of the Sun that invites weary hikers on the Inca Trail to marvel at, then descend to, Machu Picchu.

A puerta can provide access, but it can also control movement. Especially in Cuba, the wayward island we feature today. Puerta is a useful word for the airline passenger seeking to reach, say, José Martí airport in Havana, as it should lead you to the departure gate. Since I first visited in 1989 I have used a variety of puertas, in the shape of departure gates, to get there.

For as long as the Iron Curtain remained a viable piece of geo-political furnishing, the only scheduled airlines prepared to "take this plane to Cuba" were based in the Soviet bloc.

Interflug, CSA and LOT offered flights via their hubs in, respectively, East Berlin, Prague and Warsaw: trusted citizens and Party faithful were allowed to fly to the only ideologically suitable island in the West. But the crafty Cuba-bound traveller from Britain boarded a slow bus to County Clare in Ireland.

In the early 1990s, there was only one frequent (ie, better than once-a-day) link between Europe and an airport in the Caribbean. London-Barbados? Madrid-Santo Domingo? Paris-Guadaloupe? No, it was from Moscow to Havana. Ten times a week, an Ilyushin jet belonging to the world's biggest airline would set off from the Russian capital. The thirsty engines could get no further than Ireland's wild west, and, specifically, Shannon airport, before being obliged to put down for fuel.

The Irish government allowed Aeroflot to pick up passengers at Shannon. Before no-frills airlines had been invented, the airfare from London on Aer Lingus was prohibitive, so an economy pilgrimage to the island of sun, sea and socialism began at Victoria Coach Station, and involved an overnight voyage across the Irish Sea and a meander right across the Republic.

Once the aircraft (emblazoned with hammer and sickle) was replenished with fuel and augmented with passengers, it terrified the local livestock as it took off for the shortest possible transatlantic journey : to the Nato air base at Gander on the Canadian island of Newfoundland.

On one flight I was aboard, the crew missed Gander, apparently because of poor weather, and diverted to an airport belonging to the sleepy town of Stephenville. After some hours they procured enough kerosene for the final leg, but everyone's dinner remained frozen in Gander. For all I know, it might even have been goose.

In those laissez-faire days, neither health nor safety were accorded undue attention. No one batted a Soviet eyelid when I wheeled an oversized Chinese bicycle (a $25 snip in 1990) the entire length of the aircraft's aisle at Havana airport: there turned out to be little shed at the back of an Ilyushin 62 designed to house such extravagant hand luggage.

Other questionable airlines were available. The steward who asked me for a light for his cigarette as we taxied for take-off from Havana was working for Viasa of Venezuela. Flying to, from and around Cuba was fun – and provided the opportunity to stow away, as I did one Christmas Eve, on a flight from Havana.

The airline was Air Outre Mer. Our DC10 had just flown from Paris to Havana. The plane was scheduled to continue to Cuba's main holiday resort, Varadero.

In those blissfully innocent days, no passenger count was made before departure. With no checked-in baggage to collect, I simply stayed on board for the final leg. Doors to automatic.

Their axis of evil, your holiday island

What do al-Qa'ida, the Real IRA and a small London travel agency have in common? They all appear on a list that bars US citizens from "providing services or conducting transactions" with them. The clue is in the agent's name: Cubanacan UK Ltd. America's Office of Foreign Asset Control does its best to prevent US citizens taking vacations in their nearest, biggest and most interesting Caribbean neighbour – though tens of thousands of them circumvent the rule each year and go anyway. Cuba's inclusion in the "Axis of Evil" also prevents travel firms with US parentage selling Virgin Atlantic flights from London to Havana: " is unable to sell tickets to one or more of the destinations you have chosen. Please select a different destination," the website suggests. Or you could select a different agent.