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In my opinion, good comprehensive Trip Insurance is worth every penny for the peace of mind it will provide you.
No one knows what can come up at anytime. My husband and I sadly learned this on our 4th trip to Negril in April 2010 when our son-in-law (with their 1st child due in 6 weeks) unexpectedly passed away. We were in shock and having to deal with so much mentally, that at least by having purchased trip insurance we did not have added stress of the financial burden of worrying about emergency airfare to return to the States, Etc.
We always buy Trip Insurance that includes medical, dental and evacuation and repatriation of remains. Pray you never need it, but if you do you will could be out thousands upon thousands of dollars during a stressful time.
A couple weeks ago we were supposed to go back home to Calif. for a wonderful vacation. I did not purchase trip insurance because it was just to CA. Unfortunately, trying to remove a huge portions of a downed tree out of our pool due to Hurricane Irene, my husband blew his disc out and we were not able to travel. Fortunately, we were able to cancel hotels and rental car without any fees. However, we had spent nearly 900.00 in airfare which had to be used by 02/2012 so in order not to lose all that money, we scheduled a trip to Florida in February. Would much rather have had the $900 back in my pocket so I could choose where to vacation next. Even with rebooking to FL, we still lost $160+ in unused airfare.
The trip in 6 weeks back to Negril we should be able to keep since he had emergency spinal surgery, but if not, we are fully insured and it's a good feeling that we will not be out a lot of money again.
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