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Here are some questions to ask: 1. Medical emergencies. Find out who is covered inside and outside of the people travelling with you and get a list of all covered medical emergencies. Make sure you find out if the cover includes existing medical conditions anyone might have. 2. Weather coverage. If you are travelling to hurrican prone areas during hurricane season, make sure you know the specifics of the coverage. Ask how far in advance the airline and airport cancels if threatened by a hurricane and what procedures to follow to ensure that you are not stuck in threatened areas. 3. Theft o...