What is the best destination for a sunny September trip?

Q I am looking for somewhere warm in September, out of Gran Canaria, Cyprus, Rhodes or Kos. Which do you recommend?

Michael B

A You are in the fortunate position of travelling south in September, avoiding the crowds, high prices and scorching temperatures of the summer peak – as well as the airport overstretch.

The short answer is that you would have an excellent island holiday in any of those locations, so you could just pick on the basis of the best deal you can find at the time you want to travel. I recommend a proper package holiday booked with the likes of Jet2 or Tui.

All other things being equal, though, let me share my own ranking of these alluring locations.

Gran Canaria is somewhere I save for deep midwinter: the island is at a latitude of 28 north, conveniently exactly halfway between Glasgow and the Equator and delivering bright days year-round; it also has a proper Spanish city, Las Palmas, for cooler days.

I enjoyed my one holiday to Kos, but I would not return there in a hurry. “Tranquil and quietly adorable,” my notes say. I like some archaeology along with sunshine on my Greek islands. While the ruins of Asklepion are interesting – an archaic health farm – your other options are more appealing.

Rhodes Town, the capital of the fourth-biggest Greek island, claims an astonishing repertoire of influences, from classical to Art Deco. The walled Old Town is intensely beautiful, its old stones testifying to a dramatic history. Yet there are good beaches just a few minutes away too.

Because I rate exploring above lazing on the beach, Cyprus is my top choice. It has been an autumn escape for British holidaymakers for many decades, and is easily accessible via Paphos for the west of the island and Larnaca for the centre and east. Travel around the island is straightforward, and you can also build in a trip to the fascinating, still-divided capital, Nicosia.

Finally, at the risk of offering too much choice: you might also want to consider the Mediterranean’s largest island, Sicily.

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Q Last Tuesday, my flight to Naples made two attempts to land, but due to a thunderstorm it was eventually diverted to Rome. We then waited three hours before coaches were organised to take us to Naples.

During the disruption, the airline told me to claim for food and drink because of the delay. But when I filled the form out on the app it said no compensation was due as the flight “landed at your destination 54 minutes late”.

So how can I now claim the food and drink they said I could without racking up a huge phone bill to their call centre?

Jane B

A How frustrating, though I am glad that everything appears to have worked out from a safety point of view. After the captain attempted to land twice during adverse weather, he or she will – I presume – have followed standard operating procedure by declaring a diversion to the predetermined alternative airport, in this case Rome.

Although the two are only 124 miles apart as the Airbus flies, the road distance is much further. I imagine that, after a three-hour wait for coaches, you then had a three-hour journey to Naples airport – in total, six hours of your life you will never get back.

Your question, though, is whether you will ever get back the cash you unexpectedly spent on food and drink to sustain you through the delay. Initially, the airline correctly advised you to claim your entitlement to subsistence due in respect of the rules concerning European air passengers’ rights – and the simple decent treatment of customers. It is doubly annoying that the automated system appears to be programmed to register only when the plane landed, and not where it landed.

I imagine you spent perhaps €20 or €30 (£17-£25) on something to eat and drink. Yet even if you persevere with your claim, the airline might argue that you were unnecessarily indulgent and offer only half the cost. Or it could contend, for example, that a receipt for a credit card transaction is insufficient proof that you did not include a sneaky glass of wine.

Rather than getting embroiled in what could prove to be an infuriating dialogue, in your position I would put the whole unhappy episode down to experience and not pursue a claim.

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Q I am landing in New York City in early to mid-October, staying for two or three nights then going upstate for a week or so. Where should I go in New York State that’s romantic as well as exciting?

Name supplied

A To give you an idea of the scale: New York State is bigger than England, and its mightiest national park, Adirondack, is larger than Wales. October is an ideal time to visit, offering “leaf peeping”: surveying the fall foliage as maples, hickory and beech succumb beautifully to autumn.

To make the most of your week of exploration and romance, don’t rent a car in New York City. Instead, use Amtrak trains to get deep into the state – and hire a vehicle locally. You will save on stress (driving out of Manhattan can be a nightmare) as well as expense.

To begin, take one of the 10 daily trains from New York’s Penn Station, running beside the Hudson River to the pretty and historic riverside town of Poughkeepsie: just 90 minutes from Manhattan for a typical one-way fare of $28 (£23). In terms of somewhere to stay: there are a lot of chain hotels, which will be good value and reasonably central, or you might want to find an Airbnb property. Eat local food, drink New York State wine and enjoy the ambience. The stand-out tourist attraction is the Walkway Over The Hudson (walkway.org), a mile-long former railway span revived as the world’s longest elevated footbridge. The former home of Franklin D Roosevelt is nearby, and now a National Historic Site.

From Poughkeepsie here you can continue by train (two hours) to Saratoga Springs – which is where I suggest you rent a car for two or three days (Enterprise has an office, with rates starting at around $120/£99 daily). Explore Lake George, including a sightseeing cruise, and stay at Garnet Hill Lodge: a 1937 structure with an impressive stone fireplace for the cool October evenings.

The state capital, Albany, with its flamboyant Capitol Building, could make one final stop.

Finding places to stay (and eat) will be much easier if you avoid Friday and Saturday nights, which is when many New Yorkers head north. A Sunday-to-Thursday adventure represents the best value.

Email your questions to s@hols.tv or tweet @SimonCalder