Based on your infrequent use, you'll spend a bunch of time and between $1,200-2,000 installing an SSB.

You need to realize that the phone won't give you very speedy service. But you should be in Bermuda in about 4-6 days. Then you can use WiFi or some teathered Blackberry connections from more conventional land based networks.

I've heard a lot of questions about Iridium. Globestar seems to be more favorable as a source.