We just found out that Costco.ca now offers
travel insurance to Canadians, and the rates look very good too.
As far as when to buy your insurance, as others have mentioned it all depends on the specific policy and your own personal situation. For my husband and I, we are both healthy and fairly young, so I don't buy insurance until I know 100% that we both have the time off work, we're sure we're not going to change our mind on the trip, and at least 1 month prior to the date when penalties start to kick in. The policy I'm looking at specifies that it must be booked
before any cancellation penalties are chargeable, but time limits for pre-existing conditions begins when you buy the policy - for example, for our health category, they will cover pre-existing conditions as long as they were stable (by their definitions) in the 3 months prior to buying the policy. Theoretically, by waiting a month or two to buy the coverage, something could pop up and therefore be ineligible for coverage, but the chance are very slim so we take that risk. Most trip cancellation/trip insurances are non-refundable so I don't like to book them too early in case we change our minds and want to move the dates or something. Some policies also can't be bought too early - the one I'm looking at now can't be booked until 180 days before the trip, but sometimes we book our initial plans over a year in advance!
To the previous poster, I think most people find that insuring their cruise outside is a better deal financially, but I think that if you purchase through
DCL and the insurance company denies your claim for a trip you have to cancel, they will let you carry forward a good percentage (75%) to another sail date. This makes it somewhat like a "cancel for any reason insurance", but you don't get the money back, just future credit. Hopefully someone will correct me if I'm wrong on that. I'm not sure if there is a specific thread detailing DCL vs outside insurance companies.
Aby