0.33 nm separation equals
five boats in 1.5 nm.
at 6 knots this is a three minute separation between sailboats

For a plane going 1.5 nm per minute (90 knots) there is 60 seconds per five boats or 12 seconds per boat.  In a twelve minute cycle the plane could probably make three passes over the five boats. (all in the same direction)
Aerial Photo Shoot
Starting Procedure
2003
Getting to the start on time

I plan to have the coordinates for the start location in my GPS.  Then approximately three to five minutes before the start I plan to cross the start point on a broad reach.  When  we cross the start point I will record the time.  Then I will take the difference between the start and crossing time.  Then I cut that difference in half.  Then subtract that half from the start time and record it as the come about time.  At the come about time I will come about and head back on the opposite tack still on a broad reach.   The GPS will no longer be pointing to the start point.   This will probably get me to the start point within seconds of the actual start time plenty good enough for aerial photo separation.  It work well for me in keel boat races back in the late 60's.
For 60 second separtion in start times on 30 knot powerboats (0.5nm) and a plane going 1.5 nm per minute (90 knots)  there is 30 seconds per boat.  With five power boats entered in a twelve minute cycle the plane could probably make two passes over the five boats. (all in the same direction)  during this time the lead boat will have travelled
eight miles.  

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