Read the policies carefully. If your concern is cancellations due to weather, or an illness in the family, make sure the policy you chose covers you for those incidents.
Usually travel insurance programs are structured as a percentage of the cost of your trip, or for a specific period of time. Often, you will need to buy the insurance within days of making a down payment. My favorite travel insurance program is World Nomads. They’re reasonably priced for the length of the trip, not a percentage of the cost, cover most of the issues that concern me and there is no need to sign up as soon as you book your trip.
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My entire family will be loyal American Express customers and cheerleaders for life, because of the treatment my father received when he had a heart attack on an island with no hospital care. He was airlifted thanks to the coverage provided by the American Express Platinum Card. If you travel frequently to developing nations or even ritzy destinations like St. Barth with no hospitals – and are at the age or have conditions that concern you, the American Express Platinum Card could save you substantial money over typical Med-evac insurance policies. And, the card comes with other substantial travel benefits. Free entry into partners’ airline lounges; concierge services including reservations for impossible to get into restaurants; companion fares, etc.
World Nomads and other major travel insurance companies offer theft riders to cover most equipment. It’s always worth checking with your insurance agent to discover what is already covered by your homeowners or renter’s policy.
Don’t assume your home automotive insurance policy will cover you overseas. Do some advance research to find out if you’re covered and if not, what additional coverage you need to buy from the rental company. The CDW that comes with most gold credit cards doesn’t cover you for liability, so people who don’t have automotive insurance should be sure to investigate options to be sure they’re completely covered.