Each season featured two plays, mostly from Shakespeare's canon including, Henry IV (parts 1 and 2), Romeo and Juliet, King Lear, The Merchant of Venice, The Two Gentlemen of Verona, The Merry Wives of Windsor, The Comedy of Errors, Much Ado About Nothing, Macbeth, Othello, and Hamlet.
The events were also noted for not charging any admission fees; instead, the audience was invited to make a donation at the conclusion of each performance.
Actors who have performed in Shakespeare by the Sea productions include Gregor Jordan, who played Bassanio in The Merchant of Venice and who later directed the films Two Hands (1999), Buffalo Soldiers (2001), and Ned Kelly (2003).
Joe Clements who played Senior Sergeant Allan Steiger in the television soap opera, Neighbours, during 2004–2007 was in the 2010 productions of Shakespeare by the Sea.
Some of the actors who had been members of the Shakespeare by the Sea company decided to continue presenting plays at the same site and following a similar schedule, but with a different production style, under the name Bard on the Beach.