In the spring of 2005, the author, the retiring president of EDUCAUSE, was asked to be the keynote speaker at the EDUCAUSE Western Regional Conference. The conference theme was "Winds of Change: Charting the Course for Technology in Challenging Times." What that brought to his mind was the era of the great sailing ships of the eighteenth and nineteenth centuries, a topic that has always held great interest for him. In this article, he offers ten nautical maxims for charting the course of higher education IT in the twenty-first century: (1) View IT from the crow's nest; (2) Seek signs of being on the right course; (3) have a strong captain at the helm; (4) Remember that the crew wasn't shanghaied; (5) Beware...there be dragons!; (6) Hold steady in rough seas; (7) Depend on the rest of the convoy; (8) Navigate by more than the stars; (9) Navigate to the correct shore; and (10) Know when the ship passes. (Contains 13 notes.)