Questions about travel insurance

spiffgirl101

Mouseketeer
Joined
Jul 20, 2012
I have some questions regarding trip cancellation insurance. I have a cruise/Disney World vacation planned for Feb 2020. I am booking 3 one way flights through Air Miles to Orlando and then booking 3 one way flights throughback home through Expedia. I also booked a DCL cruise on my own through the website, and will be looking into where we want to stay later on.
My question is: with all these different ways I have booked things is there one place I can go through that will cover us for the whole trip? Maybe through CAA? I have medical through work, so not too worried about that, I am more concerned about emergency cancellation or bad weather.
I am going to do more research on the weekend, as I want to start booking flights right away.
I am pretty sure I need to get the Airmiles insurance? I have never booked flights through airmiles so don't know.
Any advice would be appreciated!
 
Questiions:

1. Are your flights direct or do you have a connection?
2. Are you flying in a day or more in advance of your cruise?
3. Do you have travel insurance on your credit card and have you booked everything using that CC?
4. DisneyWorld portion of your holiday, room only or package?
5. Everyone travelling generally in good health?

Depending on your answer to the above questions you may or may not need trip cancellation insurance. The fact that you have booked so many of the segments of your holiday individually means you could add insurance for, say, the cruise portion but not the flights. A room only reservation onsite after your cruise could be cancelled 5 days before your stay.

Just a few things to consider before you decide to insure your entire trip. Disclosure, I have yet to add insurance onto a holiday (we have medical through work). I like to think of it as self insurance. All the money I've saved over the years will one day go to pay for some travel mishap. But I've yet to experience one. (I like to live on the wild side when it comes to travel insurance and that is not for everyone.)
 
1. The flights through Airmiles have one connection through either Montreal or Toronto, the return flight is direct to Winnipeg.
2. We will be flying in a week before the cruise to do Disney World.
3. Unfortunately the type of credit card I have does not have trip cancellation insurance on it :(
4. I am hoping to book a package for the Disney World portion, waiting not-so-patiently for the 2020 rates to be released.
5. Everyone traveling is in basic good health.

I have never taken cancellation insurance before, but for some reason I am worried about it this time around. We have gone on 2 cruise before, and last year we went to Disneyland and I wasn't concerned. Even when we went to the UK I didn't worry about it. Maybe I am just panicking because I am using so many methods to book everything that I am worried about something going wrong? I usually just figure that my medical insurance through work is all I need. Maybe I am over thinking it...
 
I think I would worry about missing the cruise if you missed a flight. Seeing as you will be at DW for a week before the cruise and they will likely transfer you to your cruise that won't be an issue.

Your flights to Orlando might be affected by weather but the airline should book you on the next available flight. Worst case you might miss a day of your DW holiday. Weather affected our flight to California last year. The airline even put us up in a hotel overnight until we could continue with our flight. I don't know if that would happen in Canada.

Your flight home, do you know where it is flying from before it picks you up in Orlando. If it is coming from Winnipeg and then directly back I wouldn't worry about it being affected by weather. Winterpeg is good about getting flights where they are going no matter the weather. Once it's up in the air (either end) it won't matter what whacky weather is happening along the way.

If getting insurance will give you peace of mind between now and your holiday then get it. Personally, I wouldn't, but that's me.
 
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If getting insurance will give you peace of mind between now and you holiday then get it. Personally, I wouldn't, but that's me.

Now that it's all written out, I am leaning towards not getting insurance. I booked the return flight last night and chose no insurance without blinking, so I must not really want it :) Now to make sure none of us fall ill with appendicitis two days before we leave...
 
We often book our own flights using Aeroplan points and then we just have our travel agent add the non-refundable costs (e.g., cancellation costs and/or port fees) to our insurance. If we have any other non-refundable costs that are booked directly or at different times, she just adds them to the insurance and charges any additional fees. Every policy, however, is different so you have to check what it covers, when/if you can add to it, etc. but such types do exist.

Check your work medical and see how much it covers. I have work coverage but we consider it to be inadequate if there was a serious issue. I personally consider it to be very basic. Unless you've checked to specifically see what yours covers and are OK with it, you might still want to consider getting travel medical to supplement it. I've always found that, unless you work for a company where lots of people travel for business purposes, the travel medical coverage is usually very minimal since they don't consider it to be a necessary benefit.
 


I use CAA Trip Interruption insurance only when traveling to Florida during Hurricane Season.
I get my travel medical with Blue Cross. My extended medical thru Work is with Blue Cross. But I also get a separate travel policy even though work policy does cover travel. Reason being is if I incurred a trip to the hospital in the US for something, broken bone or worse, it goes toward my lifetime limit. The separate travel policy doesn’t affect lifetime limit.
 
Does your credit card have free insurance? Mine does and it also covers emergency air ambulance in case you needed to be evacuated off the ship. Every time I book a cruise, I always call to make sure the air ambulance in still included. That's a big one ($XX,XXX)!
 
We use CAA insurance because, as members, there's a discount. Have you checked with the card you used to pay for anything? It's worth a phone call to see if you're covered.
 
I mentioned it earlier, but I don't get travel insurance through my current credit card. I booked my flights and chose no insurance. I still have time, if I do go with insurance, I might just go through Airmiles (so I get my miles back in case anything happens) or CAA.

Thanks for all the input everyone!
 
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