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Squaremouth Warns Fall Cruise Bookers: Two Coverage Calls Most Travelers Get Wrong

6/19/2026

Travel insurance marketplace Squaremouth is putting Caribbean and Gulf cruise travelers on notice as fall booking season gets underway: the two coverage decisions most likely to cost them are when to buy and what to buy.

Petersburg, Fla.-based company issued the alert as Atlantic hurricane season ramps up and demand for autumn sailings builds.

The Hurricane-Season Timing Problem Squaremouth's message is aimed squarely at travelers who treat insurance as an afterthought — purchased close to departure rather than close to booking.

The company's framing implies that timing the purchase correctly relative to a storm-prone season is a distinct decision from simply selecting a policy, and that confusing the two leaves travelers exposed.

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