A graduate of the United States Naval Academy in Annapolis, Maryland, Skip earned his B.S. degree in Operations Analysis. He was also a letter-winner on the USNA Varsity Sailing Team and went on to compete in several national and North American championships, and one Olympic trials. He earned his Master of Science degree in Command Control and Communications from the Naval Postgraduate School in Monterey, California. Captain Anderson's naval career spanned twenty-four years, including service aboard three destroyers, one frigate, three aircraft carriers, and a battleship. His service at sea spanned the globe, to all continents, through over thirty countries and countless harbors.