Once, it was all so easy. Jump on a bus with Cliff Richard, sing a few songs, next stop Athens, and you were assured of the trendiest holiday of the year.
Now it's hard work impressing friends and neighbours. In the Nineties, Cliff would have to backpack along the Silk Route in central Asia or paraglide over a central African war zone to have any chance of getting hip young things to join him on a break.
Holidays are becoming more exotic as flights proliferate, resorts expand and the distant corners of the globe become cheaper. The first consumer travel guide to Antarctica will be in the shops in four months' time, and Somalia is opening up as a tourist venue.
"More and more people are wanting to travel to places that are somehow 'off limits'," said Richard Trillo of the travel publishers Rough Guides.
The knack, however, is to recognise what is a passe destination. It must be worrying for students on their year off to south-east Asia when they find that serious travellers regard Thailand, Malaysia and Indonesia as hopelessly Eighties.
Cambodia is still a good stamp to have on your passport but Vietnam is past its peak (after so many guilt-ridden 'Nam movies, maybe we feel we've seen it all before). Cuba, another old adversary of the US, stays in, as the last genuine Communist state.
The real hot spots are the ones it takes time and ingenuity to get to, such as the Silk Road, an ancient caravanning route through central Asia established more than 2,000 years ago. For those who want even more of a challenge, there is always Saudi Arabia, which does not allow tourists in. Travel gurus dream of being the first legitimate sightseer. Or the Himalayan kingdom of Bhutan, where the king personally controls the numbers coming into the country.
With the increasing availability of long-haul flights the furthest destination is no longer always the most chic, says Mr Trillo. "A holiday to the Dominican Republic in the Caribbean will now cost you about pounds 100 less than going to parts of Greece"
Cost isn't everything, however. Nothing will save Richard Branson's island of Necker from the stigma of being unfashionable. Princess Diana, Steven Spielberg and Harrison Ford may have all been there, but so can anyone with more than pounds 700 a day to spare.
Failing to book the family holiday rates as a big domestic misdeed. But it does happen. Despite an apparent glut of opportunities - discounts on holidays of up to15 per cent and, since 1995, package trips for pounds 99, even at the height of summer - the market has shrunk, writes Simon Calder. About 1 million package holidays have been taken off the travel agents' shelves, and at last supply is matching demand.
The travel trade's annual warnings about availability are, at least this year, not bluff. So what to do if you have left everything to the last minute?
First, you might try television services such as Teletext. One in seven holidays is now sold through such services and the prices are generally accurate. The Independent, meanwhile, offers its ideas based on interviews with operators. We asked for breaks for two adults with children aged 10 and 14.
Blackpool: A four-night break in Blackpool, staying at the Warwick Hotel on a half-board basis, costs pounds 330.80.
France: Anyone travelling with a carload of people shouldn't be paying more than pounds 100 return between Dover and Calais," says Chris Perry, of specialist agency, Channel One Travel, which offers a pounds 79 open return with SeaFrance. Try taking a caravan- on Stena Line, it will cost pounds 98.
Canary Islands: "Leave the children at home," advises Alan Cornish, director of Corona Holidays. "The best you can hope for is a one-bedroom, two-week deal - Los Cristianos Paloma Beach for pounds 360."
Australia: Midwinter in Melbourne might not appeal, but long-haul discount specialist Quest Worldwide says the price on Emirates' new service from Gatwick is unbeatable - under pounds 2,750 for going halfway around the world. From Manchester, one night (or longer) in Bangkok comes in at pounds 1,556.Reuse content