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Which islands for an extended vacation?

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Hello - I'm reposting this as my original post seems to have disappeared?!? I am looking for recommendations on which islands/locations would be good to visit for anywhere between a month and 3 months from about March to June/July next year. It would be great to stay at two or three different places to experience the different landscapes and cultures etc. I've tagged a few places to hopefully get some interest in my post but I'm not tied into any particular islands.

Some info to give you an idea of what I'm after - I am an Australian woman in her 30s in need of a 'sabbatical'. I'm well-travelled, although I've never been to the Caribbean Islands (only the Caribbean coasts of Costa Rica and Panama). I don't need to work (I realise that I probably couldn't anyway) and I've got a pretty good idea of the likely expenses from my initial research.

I'd like to go somewhere that is away from the hustle and bustle but still has enough going on to hopefully make some social connections. I speak very basic French - enough to get by travelling through France and Quebec etc. It would be good to spend a month or so somewhere French speaking and another month or so somewhere English speaking.

As a single female I'd prefer somewhere relatively safe. I don't need luxury but, not being the handiest person in the world, it's probably best that it's not too basic either. 

I'm really just after somewhere I can swim in the sea, read books and walk around to get to most of the places I need to go (I realise I might have to end up getting some form of private transport). Any suggestions or advice would be greatly appreciated!!

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