I've never heard of an annual insurance plan that covers trip cancellation. Usually annual plans cover things like overseas medical and emergency repatriation. They cost roughly $200-500/yr depending on what is covered.

The plans that cover trip cancellation will charge a percentage of your trip cost. And even then, as mentioned by Big4Flyer, they don't pay when you voluntarily cancel a trip. They might pay if unavoidable flight delays cause you to miss your cruise, or something like that.

I would take a look at Global Rescue and International SOS. Both of them offer a variety of annual and single trip plans, individual or family. Both are very reputable and cover (most?) extreme sports. Just make sure you understand what coverage you are buying.

There's an interesting Wired article about Global Rescue here.

HTH