Dr. Alexander Hamilton is a colonist living in Maryland in the mid 18th Century. Born in Scotland in 1712, he moves to Maryland to practice medicine in 1739 settling in Annapolis where he becomes a popular doctor. He contracts tuberculosis, which weakens his constitution, and in 1744 he decides to escape the oppressively hot summer of Maryland and tour the northern colonies. He sets out at the end of May, 1744 and makes his way through Philadelphia and New York to Boston, stopping at several smaller towns along the way. He returns to Annapolis in September, having traveled over 1,600 miles.
Unlike the other three travelers included in the collection, Hamilton travels only for his own leisure, having no particular business or destination. He travels by horseback along with his black servant, Dromo, usually stopping at established inns where he receives better accommodation and the company of gentlemen similar to himself. He lies to take part in long conversations on literature and politics, although he does not share the fondness for alcohol that many of the gentlemen he meets seem to have. He has strong opinions on religion and dislikes when the subject comes up in conversation.
In Philadelphia, New York and Boston, Hamilton lingers among the higher social classes of those towns. He enjoys attending club meetings to discuss intellectual topics of the day, although many of the discussions are dominated by the recent declaration of war by England against France.