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We have HTH Worldwide Insurance Travelguard Gold. The one time we used them for reimbursement of medical costs, they treated us fairly.
We have made a decision that we only need to cover medical and evacuation and we self insure for everything else. If we have to cancel a cruise after final payment (to date, it has never happened), we will absorb the loss.
IMO, insurance for everything else such as loss of luggage, trip delay, etc. is a total waste of money.
We have similar issues to the OP although in our case it is even worse since we travel around 5 months a year and also do a lot of cruising (99 days in the past 12 months). Several years ago we decided that trip cancellation insurance was too expensive and did not make a lot of sense for us since we seldom cancel a cruise (it has happened once in over 100 cruises). We finally decided it made sense to purchase an annual travel medical policy (quite inexpensive at about $200 a year per couple) which gives us extra coverage for medical and trip evacuation. Folks need to keep in mind that a medical emergency can have unlimited costs risk while the cost of a cruise only risks that specific cost. So we find it makes sense to self-insure the cost of our cruises (we would spend that money anyway) but never gamble on medical.
I looked into this and discussed it with Travelguard, and the problem with the policies I read was the very low coverage they provided.
__________________ We've been on Carnival: 27 voyages 184 days Celebrity: 3 voyages 24 days Holland: 15 voyages 219 days Norwegian: 2 voyages 16 days Princess: 16 voyages 154 days Royal Carib: 5 voyages 35 days Vantage:River 2 voyages 39 days
GRAND TOTAL: 70 Cruises 671 days
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Amsterdam World Cruise 2017