Only a few boats in each race have the luxury of going wherever they want on the first beat with no concern for keeping their air clear. The rest of us have to grovel for any lane of clear air we can find… Here is a suggestion for dealing with one of the toughest calls to make on a crowded beat when you are not in the top five in the race:
When to tack and head back towards the middle, while working to the right on port tack?

Obviously the closer you are to the starboard layline when you tack, the more likely it is that a boat ahead will come across and tack right on your air, because they are also trying to get to the mark as quickly as possible. If you overstand from a long way out, you not only sail a lot of extra distance, you lose if the wind shifts in either direction. And you are doubly hammered if someone comes out and tacks on you.

Here’s an alternative: Tack about a minute before the layline. You are far enough under the starboard layline that there is little reason for a crossing port tacker to tack right on you. If a port tacker is just slightly ahead, you can wave them across so they don’t leebow you. I am always impressed how far you can sail in clear air in this “underground passage.”

The next big call is when to “step up” or tack to port and get up in the parade to the mark. My advice is to do it sooner than later. Make sure you watch to see how things are shaping up there. If it starts getting thicker, get up while there is still room to get through the parade. Once on port tack, it is normally better to duck starboard tackers rather than leebow them and risk not making the mark. Of course, you can always ask the starboard tacker if they prefer you cross them… You never know when you’ll get waved across! No matter what, be sure to tack to port before you are four lengths from the port layline, so you can make your tack back to starboard outside the zone (see rule 18.3).
 
Finally, once you break on through the parade of starboard tackers, it is normally better to overstand from there, rather than risk a tight rounding in a crowd of slow moving boats.

by Dave Perry, author of Understanding the Racing Rules of Sailing 2009-2012, 100 Best Racing Rules Quizzes 2009-2012, and Winning One Designs offers up these racing tips.  Thank you to US SAILING for sharing them with us.