In reply to Nbrain:
I was going to suggest SA when I started reading your post. October is a good time to go to Western Cape which can be beautiful at that time of tear with the spring flowers coming out. The climbing in Western Cape is superb. I've climbed on Table Mountain and at Du Toits Kloof where there are some superb mountain style multi pitch trad routes. The rock is excellent with brilliant friction and the weather good. It's worth considering hiring a guide if you want to not waste time frigging around trying to see what's in condition, and what's in the shade - I can highly recommend someone if you are interested.
Some good quality scrambling routes on Table Mountain as well.
Lots of cycling both Road and Mountain Biking. The wine and food is top quality. Eating out and alcohol is cheaper than in the UK.
English is spoken and they drive on the left - what more could you ask for?
As an alternative to hiring a guide I suggest you contact the Western Cape branch of the Mountain Club of South Africa for ideas, advice and possible climbing partners.