If you are diving, you should have DAN. Regular medical insurance and trip insurance have huge holes around things like hyperbaric treatment and medical evacuation costs that are only covered by dive specific insurance like DAN. Now as for trip insurance, it really depends on the details of your trip, who you are using for airlines/operators, and what your personal situation is. One thing many people don't realize is that most trip insurance won't cover cancellation if you decide not to fly to a destination in the path of a hurricane, unless the airlines are not flying or the resort/hotel you are planning to stay at is closed. In those two instances, the airline will generally allow you to rebook another time with no transfer fee if they are not flying, and the hotels/resorts generally will give you a credit for a future stay if they are closed. So in the two instances where trip insurance would pay due to a hurricane disruption, it is very likely that the hotels and airlines will already have helped you out. Where trip insurance can be very helpful is if you have a situation such as having a sick relative or limited vacation time, such that you would not be able to travel again within the timeframe the airline or resort is willing to allow you to transfer. Or if you have unpredictable job issues that cause you to not be able to travel at the last minute. Things like that are usually covered by trip insurance. Just read the policy limitation and exceptions carefully before you buy, as many of them will not help you much if you are sitting at home the day before you leave for a trip, watching a hurricane head towards your intended destination.