Choose Travel Insurance Options
Buying travel insurance is gambling. In the long run, we all know the insurance company makes more than you do. The more coverage you buy, the more money you lose.
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So my belief is that you should only buy coverage for something that, if it happens, will cause you a significant problem, but not for every possible inconvenience, however annoying it would be. For example, I don't want my medical insurance to buy my drugs - that cost may be tough to handle sometimes, but I can pay for it myself. I want it to pay when I am hospitalized for 2 weeks - that would wipe me out financially and mess me up for years. 
Travel insurance for your baggage - Unless you're carrying something particularly valuable, such as a very nice camera, this is probably not a good option. I'm a big believer in travelling light. So if you've lost just a few outfits and toiletries, I say just take the loss, and have an adventure buying some stuff at the local market.
Travel insurance for medical - This may not be necessary, depending on your own health insurance situation, but it is also almost too cheap to risk not having medical travel insurance. It's something in the range of up to $3 per day for $500, 000 coverage. If you're spending thousands on a 2-week vacation to Europe, an extra $40 for medical travel insurance is probably worth it for the peace-of-mind.
Travel insurance for rental cars - If you have car insurance, it probably covers personal rentals under the same terms, and you won't need travel car insurance. You can call or email your agent to make sure.
If you don't have collision coverage on your own car, you won't have it for the rental car! Car rentals for business purposes probably will not be covered on your personal policy. In that case, talk to your boss, or somebody in the company that takes business trips regularly, to see if you need travel insurance for your rental.
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