Possible Clues:

• Smartarse has ways to get land
• Smart Alec's old way to get a port
• A know-all appears perceptive over the port
• Sage in unknown quantities, say, needing more care when cooked
• Smart guy with passion going about bad case
• One thinks one knows how much land is there
• Smart alec takes gang cycling round one stretch of water
• A know-all appears perceptive with port
• A know-all on the water, I take new crew out
• One affecting superior knowledge