Hollesley is a village and civil parish in the East Suffolk district of Suffolk east of Ipswich in eastern England. Located on the Bawdsey peninsula five miles south-east of Woodbridge, in 2005 it had a population of 1,400 increasing to 1,581 at the 2011 Census. Hollesley Bay Prison is located nearby. The Irish writer Brendan Behan, arrested for I.R.A. activities in 1939, was sent there, subsequently describing his experiences in Borstal Boy.