I think mid November. Somewhere totally relaxing, sunny and where there's decent medical help in case OH gets another one of his bizarre allergic reactions to something!
We thought of South Africa if can find an affordable fare, as we can stay there for nothing and car hire is cheap. But November can be dicey, or can be 23- 24 degrees and sunny, which would be lovely.
Long haul though.
Are Crete and Rhodes a bit wintry or rainy then? I don't know if OH would find enough to do in the Canaries? We love the sun, sitting at cafes, seeing beautiful or interesting places etc.