Chubb Travel Insurance
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Chubb structures its travel insurance in three tiers, Basics, Essentials, and Choice, so you pay for the coverage level you actually need. Their trip cancellation rider covers up to $100,000 in pre-paid trip costs, which appeals to seniors planning expensive vacations or taking multiple trips annually.
Chubb's annual plans let you lock in a full year of coverage rather than buying single-trip policies. This works well if you're an active retiree taking frequent getaways, though their standard per-trip options exist too if you travel sporadically.