• Slower boats start First
• "Winner" is the first to cross the finish line
• Slower boats get to lead the way and faster boats get to chase them down

The course: 

This one's best described as "Go through both guts, up to the far tip of long Island and back home. 

• Start at the "Second Red Nun" and nearest mooring ball perpendicular to first mark and head towards Nut Island / West Gut
• First Mark is the "Weymouth Fore River Channel Lighted Buoy 10" TO PORT
• From there, cross the Hull Gut through to the "Green 1" TO PORT
• Finish at the "Second Red Nun" TO PORT

In picture....