Janey I agree that Italy would be gorgeous in September (or any time for that matter). We went Rome, Sorrento, Venice and Lake Garda and I loved them all. So nice just to have a leisurely walk around and stop at street cafes for some great food and a large glass of fabulous Italian vino. If you go to Venice I recommend staying on the Lido, which is much more chilled, has an absolutely fabulous beach and is just 10 mins in a water taxi across to Venice itself. With a UK break I guess it depends on how much you value nice weather. 
I don't think you are mad with South Africa but isn't September still their Winter?
Alex after months of worrying that we haven't got a self-settler, I now truly believe it's a complete load of bollocks which is mostly pedalled by alleged sleep experts, most of which have books to sell which will miraculously tell you how do do it. Yes it's great if your baby can do it, and you should definitely give them the opportunity to learn, but it depends entirely on the individual baby's temperament and development and I don't think there's anything wrong with a baby if they want a cuddle from their caregiver in order to settle to sleep. After all, babies have evolved to want to be close to their parents to protect them from harm. I think this is a great article on the subject which he then followed up with this article - Part 1 and Part 2 which are well worth reading, especially the parts about the development of the vagus nerve.
On a personal level, when E was born she was exactly like S and had to be rocked and then put down asleep. This has gradually evolved to where we are now, which is that we wind her down before bed/naps so she's sleepy but put her down awake and and she generally settles off herself in her cot, but DH or I have to still be in view until she's asleep (which only takes a few minutes), so I don't think it counts as the elusive self-soothing, but it's still progress from where we were a few months ago. She will sleep with or without a dummy. The exception to this is night feeds where she ends up feeding to sleep if she's not waking up for 2 sodding hours and I can't be bothered to wake her up to put her back down awake when she's fast asleep at 3am, so I put her down asleep. If something is working for you why worry about it?
Hazle I am just letting her gag and vomit the food back up. 
I figure it's all a learning curve and she has to learn to chew before swallowing so as long as someone is around to make sure she doesn't choke we are just going with the flow (and cleaning up the mess!). This morning she had some porridge and a yoghurt and then I gave her a piece of my toast, which she gagged on and threw up, but I think the majority of the porridge and yoghurt did stay down.