Ryanair offer travel insurance policies as an add on to a flight booking, or they can also be purchased as stand-alone products. Ryanair travel insurance is offered in two levels, so you can choose the option that's right for you and your wallet.
Jamaica's rainy season coincides with ours here in Florida (I am in the Tampa area) for the most part. We have anywhere from 30-50% chance of rain daily until hurricane season is over. I didn't mean you have rain every day, all day from May to December in Jamaica, but I assume it is a lot like here in Florida.
Weather in Jamaica in October. October is the first full month of fall, but Jamaica still experiences warm weather. Though cooler than the summer months, high temperatures are still in the mid-80s. Vacationers should keep an eye out as severe tropical weather is particularly common during this month, but that doesn't mean that Jamaica will experience any weather troubles during the month of October.