Should I holiday in Cuba in hurricane season?

Simon Calder answers your questions on the Caribbean climate in late August, your rights when lost baggage spoils a holiday, and the world’s best railway journeys

Hot, hot, hot: Cuba and the Caribbean are great destinations all year round but autumn may be preferable (EPA)

Q I wondered if you would go to Cuba at the end of August for two weeks, bearing in mind it’s the hurricane season? Would I be safer to just travel to Europe or Turkey? I just don’t want to pay a lot and travel far for it to rain all the time.

Faye D

A One facet of travel I find constantly intriguing is the appetite of British holidaymakers to head for tropical and sub-tropical locations regardless of the climate. While I have travelled to Cuba and its near neighbours, Mexico and Florida, in July and August, they were all for what I would loosely term work assignments.

I love the Caribbean, and in particular its largest island, at any time of year. You would have a happy late August holiday, I have no doubt. But it will be hot (generally over 30C and not cooling much at night), humid and wet. Late November or early December, just after the hurricane season ends, is so much fresher in Cuba – as well as less crowded and expensive.

Late August, conversely, is a superb time to be on a southern European island: the Mediterranean is agreeably warm, the crowds have started to dissipate and you can look forward to sunny days and cool evenings.

The Balearic islands – Mallorca, Menorca and Ibiza – are a quick flight away, while a bigger island such as Crete or Sicily provides plenty of options for sightseeing. Or seek out good value and a friendly welcome in Turkey.

As always, a proper package holiday (eg from Tui or Jet2) is the optimum way to go. To keep the cost within bounds, though, try to extend your stay beyond the end of August: the deeper into September you can fly back, the lower the cost.

Greek tragedy: Nick and family’s trip to Kefalonia was marred by lost luggage (Getty)

Q We flew last Tuesday (19 July) to Kefalonia. My wife’s baggage did not arrive until Friday evening. The holiday company says she is entitled to £25 per day compensation. But I contend that the holiday didn’t start until the suitcase arrived. Those four days were just awful. There were no clear answers from the company about when it would arrive, and we were left to do our own investigation work. What would you regard as reasonable compensation in these circumstances?

Nick S

A Sorry to hear you endured that sinking feeling when a piece of luggage fails to appear. Then you suffered the stress that follows as you try to find out what has happened to the baggage and whether it will be joining the holiday. Your heartfelt description of the impact on the trip suggests that you feel a refund on the first four days of the package would be a fair settlement. Sadly, I fear that even the best lawyer would find it difficult to secure a payout for the indisputable faff and upset involved in trying to track down baggage in this tough summer.

The holiday company appears prepared to pay £100 in compensation. I would accept that settlement – with the proviso that it is on top of the costs of essentials such as basic clothing and toiletries. I trust that the firm made clear its liability to pay a reasonable amount (typically £100) for those items.

A reminder for your next trip: please approach your packing with the assumption that your checked bag will go missing and never be seen again. Pack everything essential in cabin baggage. While outright loss is most unlikely, adopting such a mindset is valuable. If a bag goes astray, your reaction can be an “Oh, well” shrug. You can leave airport and holiday company staff to sort out the mess and get on with your much-needed escape.

I hope you can at least enjoy what remains of your holiday.

The rail deal: Ribblehead viaduct on the celebrated Settle-Carlisle route (AFP via Getty)

Q My sons love trains. What’s the best train route you’d recommend anywhere in the world?

Carie L

A The route that popped straight into my head was the astonishing Cascades train between Seattle and Vancouver, along the Pacific coast. I have made the journey in both directions and it remains one of my absolute favourites. Although other rail fans may prefer dramatic mountain journeys, the constantly changing shoreline – the fact that it runs between two of the world’s great cities – makes it compelling.

For something closer to home, I shall offer my favourite routes in each of the four UK nations. From Derry/Londonderry around the shore to Castlerock is mesmerising: estuary, clipping the end of the runway at City of Derry airport, beaches, cliffs ….

In Scotland, controversially, I suggest the line from Ayr down to Stranraer: your boys might be fascinated by the several stops for the driver to pick up the token that entitles him or her to take the train along that stretch of line. It is one of the routes for which there is no road alternative. The same applies on the Settle to Carlisle line across the Pennines in England – which I prefer to call the Leeds to Carlisle line, because those are the stations at each end. You can also get some really good value fares on the line between the two cities – and if are planning more extensive travels this is a really good alternative to the West Coast main line between London and the last station in northwest England.

Finally, Wales has an abundance of riches. In a crowded field, the Cambrian Coast line from Machynlleth to Pwllheli winds around the nation’s most delicious stretch of coastline, with outstanding beaches dotted along the route – another attraction for your boys.

Email your question to s@hols.tv or tweet @simoncalder