Eight common mistakes people make when booking a winter sun holiday

Beach hoilidays winter sun travel mistakes booking
In winter, the prospect of escaping for a week or two of blue skies and warm sunshine seems more and more attractive - Getty

Winter has yet to truly show its teeth this year. But it surely will, and then the prospect of escaping for a week or two of blue skies and warm sunshine will suddenly seem more and more attractive.

Unlike seeking summer sun in the Med, however, finding the right winter-sun destination can be much more challenging. You are less likely to be familiar with the climate, the journey or geography. So here are the main pitfalls to watch out for.

Hitting the rainy season

I will never forget a plaintive phone call I once received from a friend who had just flown to Tobago in late November assuming the Caribbean was always sunny in winter and found it poured with rain for a week. His assumptions were flawed in two ways. First, the climate varies from island to island across the regions.

Second, had he checked, he would have found that November is the second wettest month of the year in Tobago. Such regional variations are common in tropical and sub-tropical regions – even within the same country. The dry season for Phuket on the west coast of Thailand is December to March, whereas only 200 miles away in Koh Samui on the east coast, it’s from February to April. So check before you book.

Tempting jet lag

Most winter sun holidays last only a week or so and yet to get there, you will probably cross five or six time zones. That gives just enough time to adjust to the time in your destination, before you fly home and start the whole process again. It’s fine for some, a nightmare for others. Avoid the agony by flying as straight south as you can.

Losing sleep on the plane

The biggest downside of a long-haul break is that at least one flight is very likely to be overnight, meaning you either arrive, or return home exhausted from lack of sleep. One way of mitigating the misery at a little extra cost, is to book with an airline offering a premium economy cabin. I quickly found an excellent option on the BA website.

The overnight flight from Barbados to Heathrow on January 26 was £434 in economy and a hefty £1,559 in premium economy. On the same night, the BA flight back to Gatwick was £281 in economy but only £624 in premium economy. The total cost of a return from January 19 to 26 with outbound in economy and overnight back in premium, was £929, compared with £625 travelling both ways in economy.

flights winter sun long-haul sleeping booking mistakes travel holidays
The biggest downside of a long-haul break is that at least one flight is very likely to be overnight - Getty

Flying too far

For a week’s break, flying for much more than eight hours doesn’t make much sense to me. Unless you have longer to spend away, forget the Far East and stick to the Caribbean, Africa and the Middle East.

Not flying far enough

I’m mainly thinking here of the Canaries. While they might seem like a good option (flights are about 4hr 30min and temperatures are usually perfectly pleasant during the winter) don’t expect real heat. For that, the nearest option is Luxor (5hr 15m) or the Gulf (7hr).

Leaving it to the last minute

There are only two windows during the winter sun season where you have a decent chance of getting a good-value last minute deal. The first is from now until mid-December. The second is the first two or three weeks of January. Start searching for discounts a week or two before Christmas. For all other times, you are likely to be better off booking now.

Forgetting jabs

Some long-haul travel vaccinations need to be administered or boosted weeks before you travel – check well in advance.

Not booking a package

Package holidays can stifle our sense of independence. But when it comes to long-haul sun and sand – where there are fewer return flights and it’s harder and much more expensive to get home if anything goes wrong then they come into their own. Book through an agent (such as or an operator (such as or and not only will your money be protected, but also you will also have support if you need it.

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