Depends on so many factors....how does one possibly answer this question?
Last year when I went on a week long trip on Lake of the Woods in Canada, we had to get to the daily anchorage, otherwise we were screwed. The first day, it was a 25 mph beam reach to get to where we were going. We had all we could do to keep the boat under control, and what a ride it was!
Besides...if you never have your tummy in your throat, how are you ever going to get better? Just make sure you have safety gear, that someone knows where you're at, etc., etc. At least then when you drown, your heirs can sell your boat! Ha! Just kidding!
C ya,
Tim