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Yes there are many issues to consider, i have done some comparison website searches, and indeed £5000 does seem to be the maximum on a straightforward search. I guess it might be worth while contacting the individual companies. i had thought of contacting an insurance broker, a friend who lives in new zealand, does that when she comes here because they underwrite her personally she finds it comes cheaper which surprised me. Good point about house insurance, i think ours allows us to be away for 40 days, but i think there is the facility to increase that. it's due around the time we would be going, so could do it just for that year. We have taken extended trips before, so i am pretty sure it was do-able. As far as buying a policy as soon as you are booked, yes definitely you have to do that, even if you are booking many months in advance. we went to brazil this year, and booked it 10 months in advance, but had to get the insurance policy organised straight away, very important if you have any medical conditions, as anything can happen at any time. I can imagine how frustrating it must be to be unable to get insurance, but having experienced two medical interludes with a relative, in the USA, one situation requiring a triple bypass, and the other surgery and intensive care for a burst appendix, i shudder to think what would have happened had they not had insurance. they would have lost their house for sure. They don't travel abroad now because the one who had the bypass has become un-insurable. Also, even if you have no medical conditions, anyone can be in an accident, we do know someone who was and ended in intensive care also for 2 months, in the USA. Its very scary. We do have some bucket list places, but i wouldn't want to risk my house.