Rindge's travels began with a journey across the Atlantic on the "SS Baltic". He then traversed England, France, and Germany, among his many stops. Upon returning to America and Harvard, he soon fell ill again and was forced to drop out of school, moving back in with his family. He was so severely ill that his doctor suggested he might find a better chance of survival if he sought out a warmer climate than Massachusetts could offer, which led him to St. Augustine, Florida. As he was again on the upswing of recuperation, he explored the town, then quite remote, and even partook of some amateur excavation of long-abandoned native Timucua villages. Later, in Colorado, he would spend a brief period as a sheep rancher.