Lennox hosted a banquet for the Duke of Holstein, brother of Anna of Denmark, on 25 May 1598. Lennox joined with the "Gentleman Adventurers of Fife" in a controversial project to resettle the Isle of Lewis. The king gave him the title Lieutenant within the bounds of Lewis, Ronalewis, and Trouternes. Lennox intended to go to Lewis in October 1598, and in December he was at the Bog o'Gight with the Earl of Huntly and planning to go to Lewis when the other adventurers or Lewisers arrived there.