There are a number of ways to approach the windward mark, and each has its own chess-like moves that can make or break the rounding. One of my favorites is when two boats are on port, one to windward ...

The stress-free and safest port-tack approach (above, at left), aka Tim's Lane, is a port layline that's just shy of the three-boatlength mark zone with a tack below any boats that are overstood.