Simon Calder: These Boots rules are made for Washington

Badges of honour are worn by many in travel: holidaymakers successfully repatriated despite holding tickets on Silverjet/Zoom/XL Airways; people who protest against airport expansion and have the principles to desist from flying; and, a new category, backpackers who have successfully made an insurance claim under the "Incarceration" section of their Boots Gap Year travel policy.

This innovative cover provides up to £1,000 for a parents to visit you if you are imprisoned during your trip. To qualify, just get banged up for a fortnight by the local judiciary. So long as "there is no chance of you being released within two weeks," your mother or father can claim cash to visit their hapless (or hopeless) offspring.

My parents could have done with this years ago. They would by now have enjoyed free holidays to many of the finest penitentiaries on the planet, given the way I attract the attention of police from Honduras to Havana. Last Saturday, for example, I was apprehended by the constabulary in south London's Battersea Park for the second time in as many months for wearing suspicious attire.

On the first occasion, I was wearing a tuxedo on my way to present a prize at the British Travel Awards, which a policeman deemed incompatible with my status as a cyclist. And last weekend, after attending a matinée at the Royal Opera House, I was sprinting smartly to pick up my repaired cycle from the bike shop before it closed at 5pm; the plain-clothed officers on this occasion festively offered a lift. Similar benevolence was shown by a state trooper when I was walking down a highway in Everett in the Pacific Northwest: he drew up alongside me in his police cruiser, demanding to know where my car was, and then bundled me into the back. My uncertainty about whether I was under arrest or merely getting a free ride, ended when he dropped me off at a nearby mall and told me to catch a bus. This run-in with the law has not deterred me from returning to Washington State. I have also happily returned to southern Transylvania and the Cuban capital – both places where I have been nicked for taking photos.

But if you have offspring who are heading for Cuba as part of their gap year, cast out of your mind all thought of a holiday in Havana while they serve their time at the Combinado del Este prison (or, indeed, Guantanamo Bay). If you happened to read this column five weeks ago, you may guess the exclusion clause on Boots travel insurance: "No cover is provided under this policy for any trip in, to or through Afghanistan, Cuba, Liberia or Sudan". The worldwide travel cover from one of Britain's most trusted brands is not valid for the Caribbean's largest island.

In the unlikely event that you were paying attention on 22 November, you will recall that the excellent Direct Travel Insurance firm suddenly withdrew cover for Cuba, shortly after being taken over by the US giant, AIG. I was told this was because the last bastion of communism in the West poses "unacceptably high" risks to holidaymakers. Now, loyal Boots customers are discovering they are not covered for the country currently run by the Castro Bros (you know, the duo that has proved more successful and enduring than Lehman Bros). Boots says: "AIG UK are the underwriters for the Boots Travel Insurance policies as we find they give excellent customer service and value for money. AIG UK make the decisions regarding which countries the policies cover. We do all we can to make our policies and exclusions clear to our customers".

Despite the apparent dangers, Boots has not advised its 70,000 staff to avoid travelling to Cuba, and is seeking "alternative arrangements" to cover people going to the island.

As Fidel and Raúl prepare to celebrate, on New Year's Day, the 50th anniversary of the revolution, they will worry about the attitude of President Barack Obama; gosh, I enjoyed typing that so much I have to do it again: President Barack Obama.

They do not fear the new leader will, like the past 11 presidents, be beastly to Cuba; they are scared that he will be kind to the island, and erase the ludicrous economic boycott that has provided the Castro regime with carte blanche for supression of human rights for nearly half a century.

Meanwhile, in the final, dismal days of the discredited Bush regime, Boots is letting itself be walked all over by Washington.

D on't tell the Americans

Boots is by no means the first big British company to have fallen foul of America's laws against trading with the enemy (in the shape of that chap with the beard and big cigar).

In the 1990s, the tour operator Inspirations was, for a time, owned by the US company Carlson. Its in-house travel agent, AT Mays, was forbidden from selling a single trip to Cuba. And in 1996 the Helms-Burton Act tightened the screws on anyone dealing with the island, for example by threatening to exclude from the US the directors of foreign companies that traded with Cuba.

At the time, Britain's biggest tour operator, Thomson, had a programme to the island of sun, sand, sea and socialism. It was promptly axed.

Alan Pugh, head of product for TUI Travel UK, which owns Thomson, says, "We were then owned by the Thomson Corporation which was technically Canadian but which had most of its profits derived from its publishing and financial empire in the United States."

Now that Thomson is part of a giant Anglo-German combine, the pressure is off, and Cuba is back in the brochure for 2009.