I have annual insurance from Staysure, but with medical conditions declared the maximum stay is 31 days. It may be that you'll need to buy single trip policies to cover each visit. A problem with sussing out travel insurance companies is that just about every review you read only covers two issues: the ease of using the website; and what the price is. Neither is of crucial importance to me. What matter is whether or not they look after you when you are ill or injured abroad. If they aren't any good at this, or have a record of finding tiny-print quibbles not to pay out, you might just as well travel without insurance. Staysure coughed up for a ten day stay in a private hospital in Marmaris, flew a doctor out from the UK and gave me escorted medical repatriation - ambulance to Dalaman, business class flight to London via Istanbul, ambulance to Bristol. No quibbles at all and they were willing to insure me the next year! Mind you our annual insurance is £460 - of which Hilary's share is probably £25/£30.