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Travel insurance for over 60s - advice please

My Mum (age 60) is going on her annual trip to Rhodes with my Dad in August and I normally get them joint cover but my Mum is also going away in September to Canada to visit relatives so thinking of getting her annual cover for both trips and my Dad separate insurance for a one off holiday as they are very unlikely to go away anywhere else abroad before next August.

My mum has a few medical conditions (high BP, underactive thryoid) so this is pushing up the quotes but just wondering if anyone can suggest any companies that are good to go with? And if I am doing it the right way - Mum 12 months cover, dad one trip?

Thanks for any suggestions in advance :)

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