I can tell you what we bought and what it covered. But, you will have to decide what you want to cover and find a policy for that. Insuremytrip is EASY and they have agents to answer questions on line for you right away.
We bought a policy to cover a $12,000 trip in 2010. We paid $180 for the poliicy. At the time, the biggest thing I wanted covered was emergency evacuation. I figured that my health insurance would cover the rest. And, of course, i wanted to be reimbursed if we had to cancel due to health of one of my family members.
We ended up having to leave the
Disney cruise on day 4 of 7 when my son needed his appendix removed. The insurance company covered ALL of his medical costs (including his food and food for my husband at the hospital). They covered the rest of our family to stay in Mexico in a resort near the hospital. It covered my taxi costs back and forth between the resort and the hospital. They made the arrangements for us to get back to the US. They covered our visa fees, flights, taxi ride back to our house, and all the doctor bills from the cruise doctors. They also reimbursed us for 3/7 of the cost of the cruise plus a few other small things. Overall, they paid out over $48,000.
Things they did NOT cover - food for the rest of us while staying in Mexico while ds recovered. And, our phone bills back and forth from my husband to me. I tried to argue that they were to arrange transportation, but they didn't have it.
When we were with the doctors, the Disney staff was wonderful and they told us that very few insurance policies will cover the entire family to get off the ship. Usually they will cover the sick child and one parent. Can you imagine leaving your child in a foreign country while you continue on vacation? Anyway, we were lucky as ours did cover us (up to a certain dollar amount - I think it was 1.5x the cost of our trip - so they would have covered $18,000 for everything but the medical portion - that was separate).
I would write down the things you think you might need. Ask the questions of the agent and pick the right policy. It really should only take you about 20 minutes or so.