Before the Start
Starting position is critical.  The lead boat holds a definite advantage, sailing upwind on the opening leg.  Therefore, the pre-start maneuvering is part of the race.

Each contestant is assigned an end of the starting line to enter the pre-start area from the course side, no more than four, but no less than two minutes prior to the start gun.  At this point, the two boats will engage each other, trying to sail within the rules while either forcing the opponent across the starting line early (in which case he will have to return and restart while the lead boat sails off on the course), or holding the opponent behind at the start.

A common tactic is for the two boats to circle each other tightly until one or the other sees an opportunity to either force his adversary into a mistake or sail away clear ahead at the start.

Upwind Legs
Upwind, the lead boat can block or `spoil´ the wind of the trailing boat.  The objective for the lead boat is to stay between the trailing boast and the upwind turning buoy (marker), lengthening is lead if possible.  Meanwhile, the trailing boat will do everything it can to overcome its rival and take the lead.  Tactics include forcing the lead boat into a `tacking duel´ (repeatedly tacking while hoping your opponent will match you move for move, but less efficiently) or causing the lead boat to sail to an area of the course with less wind or adverse current.

Downwind Legs
The second and fourth legs race downwind, giving the trailing boat a slight advantage, with the opportunity to block the wind of the lead boat.  Since the finish is downwind at the end of the fourth leg, there can be frequent lead changes on the final leg, leaving the outcome of the contest undecided until the final seconds.

Rules and Penalties
In match racing, there should never be contact between the racing boats, and one boat should not infringe a rule to gain an unfair advantage.  Rules place the onus of staying clear on one boat or the other, depending on their positions. relative to each other and several other factors.  Since the boats´ orientation to each other and the wind is constantly changing, the burden is constantly shifting from one boat to the other.

On the water umpires follow each race and determine immediately if a rule has been infringed.  A penalty is assessed that can be taken (as a `penalty turn´) at any time after the start and before the finish, allowing the race to continue, and not necessarily decide the outcome.

The Course
The course is a simple "windward-leeward" set in Charlotte Amalie Habor.  Mark rounding will be designate primarily starboard (rounding in a clockwise direction).  The race will finish on a downwind leg.  Course length, number of laps, and orientation to the downtown waterfront viewing area will vary depending on the wind and current conditions; courses ideally should provide for individual races of approximately 20 minutes duration.