Annual Travel Insurance?

I have never taken out annual travel insurance,

• Is there anything I need to look out for policy?
• Recommend any good insurance companies?

Take following points in mind before taking policy -
1. What is the maximum length of any one trip?
2. Is there allowence for Skiing/Extreme Activities at any point?
3. Baggage Claim Limits?
4. Medical Calim Limits?
5. Do you have any medical problems that need covering?
6. If you buy a couple or family policy, can they travel independently?

All the best for your travel.

Thanks Confused for answering my query.
I have one more question - Do insurance company offer family discounts for travel insurance?

No there is no family discount on the policy. But there is corporate group discount for big corporates.

Sorry, I was away for few days. Please check - LastWarrior answer, It's perfectly right.