We usually go somewhere in August, but are having to go later this year. Thought I'd put a list of what we'd like in the hope that you lot have some great recommendations! (I always like first hand reccs as opposed to just looking at random listing's!)
End of Oct (half term)
Temp warm enough to sunbathe/swim (mid 20s at least)
Shortish flight - 4 hrs absolute max
Beautiful scenery & view
4 to 5 star hotel with good TripAdvisor rating
Near the beach
Good hotel food
Nice pool
Some hotel entertainment (although let's face it, it's usually rubbish!)
Nice places to eat away from hotel on an evening
Close to some nightlife - we love cheesy tribute act nights and things like that!
Not all closed up for the season (as half term extends into November)
We love Greece, but don't think the temp will be high enough at that time of year, so we're thinking one of the Canaries but if my demanding list rings any bells with anywhere lovely you've been, please let me know? xx