Okay... I'll claim the "dummy" award for this one. Thanks to P45cal for solving the initial ship phase.

So here are the assumptions:
1. Both Ships leave at the same time ( yes I waved the magic wand and converted the time difference to zippo.)
2. The red ship commanded by P45cal (for the Good Guys) leaves New York) on the 1st at noon.
3. The blue Ship commanded by Paul Hossler (for the Darth Vader crew - sorry Paul, but your name was drawn out of the hat) also leaves Le Harve at the same time.
4. All weather, tide and spin of the earth conditions magically convened the same effects. (Man I love this Magic wand - any one want to buy it?).
5. Somehow during the night of the 3rd day both ships pass Port to Port with a flurry of flag signals ( Yes I too wonder why the British Admiralty require this procedure. By the way the Cook's second mate was seen to have flipped the bird at his 4th cousin on the opposite boat, and will be keel hauled at 6 am tomorrow morning).
6. Every twelve hours after this the Red boat shall pass a Blue boat until 84 hours shall pass.
7. The blue boat in Le Harve shall be considered as "Passed" even if anchored ..... I'm making them rules again, pass the champagne to all the crew.

So 8 vessels in total

So what is the answer if the vessels are continuous and already in operation?