7 Night EC During Hurricane Season?

I looked into trip insurance, but all the fine print and all the hoops they make you jump to collect wasn't worth it. I just make sure I travel the day before the cruise and so far have saved 1000s with never getting trip insurance.
I've made two travel insurance claims during the past year. It was not a difficult process, and I got the money I was entitled to promptly. Just fyi.

I don't typically insure domestic travel, but I always cruise with insurance, and get insurance when otherwise leaving the country, because medical plans often don't pay out for foreign health care, and if there's a real emergency and someone needs to get airlifted from the ship or an island to go to the nearest hospital or back to the U.S...Well, I don't want to spend my life savings or go bankrupt for that, personally. It can easily cost 6 figures for an emergency airlift. I'll gladly spend a couple of hundred bucks on top of the thousands I'm already spending on cruise fare or other international travel, to insure my financial security if such an emergency were to occur.
 
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Since our honeymoon cruise was officially cancelled yesterday (our wedding has been postponed as well) we are looking at sailing in September in the EC. What are your favorite excursions and ports? Also, I’m a little worried about sailing during hurricane season. How does insurance work with this and do you recommend it?
Sailing during hurricane season is always a roll of the dice. The odds of nothing happening are in your favor, but still, there is a very real possibility that your plans could get disrupted or cancelled due to a hurricane. It happens to cruisers almost every year- you just have to hope you'll be lucky and it won't be you.

Yes, you should always get insurance when cruising (see my prior post), but you need to be especially picky about the insurance you choose when sailing during hurricane season. You want your cruise, hotel, and flights to all be covered in case of a disruption, because it's very possible that while your cruise could get cancelled or rescheduled, your flights & hotel would not, leaving you on the hook for those charges for a vacation you didn't take.

Shop around for plans. Personally, if cruising during hurricane season, I would book the flights and hotel stay through DCL, and use their insurance, so if the cruise is disrupted or cancelled, they'll take care of everything. Especially if the cruise is cut short or lengthened due to a storm, it would be nice to have DCL to reschedule the flight for me while I'm cruising, rather than have to drop everything & try to reschedule while I'm onboard.

But that isn't the cheapest option, and a lot of people sail during hurricane season to save money, so... I've just read too many posts from people who got burned during hurricane season to not be uber careful. Others would have a higher risk tolerance.

But the bottom line is yes, you should cover your trip, somehow.
 

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