So what are the smart heads telling us about this year hurricane season? I’m thinking of starting to plan our 2019 winter vacation and don’t want to loose another deposit.....

Trip insurance!!! God forbid SXM gets hit again this year and there's no way to know. But if you're worried about it, just get trip insurance. If you're buying beforehand through Insure my Trip, you can buy "cancel for any reason" insurance. There you go.

The approaching hurricane season should mirror last years' hurricane season, unfortunately. Very little has changed with the climate this year. La Nina is still in place and is forecast to change to neutral by May (this month) but it has not done so yet. So the projections are still for an above normal hurricane season.

As Carol suggested, get trip insurance and hope for the best!

Not sure if trip insurance will work. I could be wrong but isn’t it only works when you are buying a package-ie flight, accommodation etc from the same source? So if I’m dealing with the property owner directly or via VRBO and then a month later I buy the flights from the airlines or a discount travel agency.... will that work with travel insurance?

Check each source. Everyone offers some kind of 3d party insurance. And check your homeowners policy to see what travel losses they may cover as well You can also get a single trip policy from many insurance carriers.

Again, if you go with a package that involves cancellation for any reason, then you are good. It has nothing to do with a package deal It costs more and you have to book it within a few days (like a week) of when you book. But it definitely can be done..

Notice that you are a fellow Canadian....We get annual travel insurance from RBC (Royal Bank) they offer single trip or multi trip. Very reasonable.

Will they be able to insure the airline tickets and the accommodation that we arrange via VRBO or AirB&B? As I mention before, we usually reserve the accommodation and then wait to buy flights when they go on sale.

VRBO offers insurance. You might want to get it directly from their provider. www.proper.insure/homeaway We've been quite happy with the product we get from insuremytrip.com. I know it's overkill, but I usually get skymed as well because I think they provide better benefits in terms of medical flight. Of course, you will want to speak with whatever provider you choose to make sure they fit your requirements.

Don't know about that Canadian provider but for Insure my Trip, it doesn't matter who you book through, you just insure an AMOUNT. And if you do decide to book through Insure my Trip, please do so through the link here on TTOL. If you book through this link, TTOL gets a small commission, and your cost is exactly the same.

Another option is to find a place that does not require a deposit (just a credit card number to hold the reservation). This, of course would likely be for shorter stays of two weeks or less. Last year we were all set to stay at Palm Court in the Orient Bay area in late November/early December and they did not require a deposit of any type. When Irma struck there was nothing to be refunded. The airlines allowed us to rebook at no additional charge as long as we made alternative flight plans within a six month window. So, we opted for Cancun instead. And, as mentioned above trip insurance is readily available and often quite affordable. No need to worry.

Our chase credit card returned our room deposits for Irma and we did not purchase any insurance. Just a thought.

Ok thank you folks, lots of good info here as usual. Will look into what options I have here in Canada.