Multitrip.com
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Multitrip.com has operated since 2000 and specializes in exactly what the name promises, unlimited trips within a single annual policy. You're not restricted to a set number of holidays per year, and each trip can run up to the policy's maximum duration. Standard benefits include trip cancellation if plans fall through, baggage cover for lost or delayed luggage, and medical expenses abroad.
This suits frequent travelers who take many short breaks rather than a few long vacations. If you're the kind of person who takes a weekend trip, then another one six weeks later, then another in the autumn, an annual policy here costs less than buying separate coverage each time. The unlimited structure works especially well for business travelers mixing work trips with leisure getaways.