I don't know about SkyMed in particular, but SOME insurance DOES cover for pre-existing conditions. Usually this is only if the insurance is purchased within a very short period of time after you book the trip, say a week or so. In addition, while it doesn't help if something happens on island, but some insurance also--for an extra fee--allows you to cancel FOR ANY REASON prior to your trip. This would help if, for example, you had a pre-existing medical condition which you couldn't get covered and you suffered a setback at home prior to the trip or decided you should not risk the trip, with a medical condition you have. You can compare all kinds of different coverages across many different companies by checking out Insure My Trip. They are a TTOL sponsor. If you book THROUGH THE LINK HERE ON TTOL, your cost will be the same, and TTOL gets a small commission.