I use Google Calendar extensively both at work and for personal purposes. I run it in HTTPS mode, so all my web-based interaction with it is encrypted. Of course, I also have it configured to send alerts by email and SMS, and neither of those are encrypted, but those are optional features. In terms of privacy settings, nobody else can even see your calendars unless you make them public. You can, however, share calendars with other individual users, as long as they have a Google account. You can also flag individual events as private. As for Google reading private calendars, I'm sure they could if they wanted to, but I doubt they would be interested. For one thing, unlike tracking the sites you visit and the links you click while browsing the web, there's no useful way to mine calendar events to make money, through advertising or anything else. Google Calendar's privacy policy: "Google takes your privacy as seriously as our own. We won't share your personal information with anyone, except under the limited circumstances required by law."