Yastrzemski attended St. John’s Preparatory School in Danvers, Massachusetts. He played baseball for the school team and was chosen as team captain in his senior year.
He pledged to take a baseball scholarship so he could enroll at Vanderbilt University. In the event that he wasn’t chosen in the first round of the 2009 Major League Baseball (MLB) draft, Yastrzemski, who was anticipated to go in the early rounds, said that he would attend college.
The Boston Red Sox selected him in the 36th round (1,098th overall) in the draft. Yastrzemski enrolled at Vanderbilt to play baseball for the Vanderbilt Commodores rather than signing with the Red Sox.
Yastrzemski began playing with the Commodores in his first season. In the summers of 2010 and 2011, he played for the Cotuit Kettleers of the Cape Cod Baseball League.
After his sophomore year, the Seattle Mariners selected him in the 30th round of the 2012 MLB Draft.