In order to resolve this situation without breaking the rules and creating a hazardous situation  (pick the correct choice):

A. Leeward must hold her distance from Windward since Windward is already pointing as high as she is able.  As long as Windward is sailing her “proper course” to the mark she cannot be forced to tack into an obviously disadvantaged situation.

B. The rules require Windward to keep clear of Leeward.  Therefore, since Windward cannot point higher, she must either slow and allow Leeward to pass safely in front or tack away no matter how undesirable that may be.

C. Windward has the right of way since she is to starboard of Leeward.   Leeward must fall off.

D. Neither boat has right of way since they are on the same tack.  They should proceed in parallel until one boat pulls ahead of the other.

See below for answer.
 
 
 
 
 

Answer:
In order to understand which rule applies, we must first determine: Are the boats on the same tack and are they overlapped?  Clearly Windward and Leeward are on the same tack.  The definition of overlap is copied below.

Clear Astern and Clear Ahead; Overlap -- One boat is clear astern of another when her hull and equipment in normal position are behind a line abeam from the aftermost point of the other boat¹s hull and equipment in normal position. The other boat is clear ahead. They overlap when neither is clear astern or when a boat between them overlaps both. These terms do not apply to boats on opposite tacks unless rule 18 applies.
According to both the description and the diagram, the boats are overlapped.

Neither boat is tacking, there are no obstructions and both boats are attempting to sail their “proper course” to the mark.  Therefore, Rule 11 applies:

11. ON THE SAME TACK, OVERLAPPED
When boats are on the same tack and overlapped, a windward boat shall keep clear of a leeward boat.

Choice B. is correct.  Windward must do whatever is necessary to keep clear of Leeward.  In this case Windward must either slow herself sufficiently so that Leeward can pass safely in front or tack way.  The fact that both options are tactically undesirable makes no difference.  If Windward fails to yield she has broken the racing rules as well as the “rules of the road”.

A current rules book is included as part of membership in U.S. Sailing – check for membership information at http://www.ussailing.org   The rules are posted on the International Sailing Federation Web site at http://www.sailing.org  Check out the M.A.S.T. web site for additional information.