Figure out how to get as much real time, continuous, info on the fleet from race HQ as you can. Since they'll know with a high degree of probability where the fleet will be, & when. That way you can loiter several hours, or even a day upwind, & move to intercept when their tracks firm up.
And by loiter I mean essentially hover over where their projected track will be, making a bit of gain to windward with each tack, but not being in full upwind mode. That way you're not beating the stuffing out of yourself, your crew, or the
boat, while giving yourself a bit more sea room to "catch up" if their track changes. Catching up being shifting your position to
wind up in front of the fleet so that they sail overtop of you at speed. Since you obviously can't catch them should they pass you.
I'd say that once their track firms up, probably beam reaching back & forth across their projected path would be the way to go. Or perhaps pointing a bit higher than 090 relative wind. That way you make good speed, & once you know the best CPA solution to meet them you can drop down to 110 AWA to stabilize the boat, while still moving well (fast) & not losing much distance "upwind" relative to the fleet.
It's a CPA excercise, where you want to have your track crossing in front of theirs by quite a bit. So that if/when things change, you have enough buffer distance to correct for it. Letting them come to you:
Much as the submarine wolf packs did in WW I with merchant fleets. Sprinting only when you know that you're in a good spot to definitively cross ahead of them. Which is how the submarine packs "caught" their faster prey at sea; sprint & drift, laying in wait along the most likely routes. Since on
battery power, in stealth mode, they couldn't come close to matching the speeds of the surface ships. And often not even when they were on the surface using their diesels. Which, then, they were supremely vulnerable to the
deck guns on the merchant's & their escorts. Let alone if those ships guarding the fleets had torpeedos &
depth charges.
Or watch
The Hunt for Red October. Similar strategy, great film... "From the hounds to the hunters".
Part of the Russian fleet chases Red October at high speed, driving her towards the other part of the fleet laying in wait for her off of the US coast. Ancient hunting trick.
Note that the closer the fleet gets to the finish, the more they'll tend to bunch up, just as happens at a race's start, or when rounding a mark. So they'll be easier to intercept there, or near there, than in the open ocean. As when they're still a good distance from the finishing gate, if there's a notable wind or
weather shift, their track could alter significantly. Or in rare instances, the fleet will split apart into 2 groups, instead of covering each other.
It would also be worth seeing if you can get some gyro stabilized optics, like a
camera (both still, &
movie in one ideally) & connect them to a big
screen through your
laptop onboard. Though even a regular
camera with plenty of zoom will do, as the shutter speed is fast enough to remove most of the relative motion. Or you can purposefully leave it set slow, for that blurred, speed effect. So that it gives the sense of the boats moving fast.
Obviously objective lens size, glass quality, lens coatings, &
software are the biggies in this equation. But you can do quite well from a distance with even a 35mm film camera with a 210mm zoom lens.
Also, have a plan to clean &
service them afterwards, including if they get douched. Most things are saveable from such incidents if you act relatively swiftly, & wisely.
Might post a thread too asking for feedback on what world
work in terms of a drone to get you good pics at some distance. As they can make fairly stable imaging platforms as compared to a boat's
deck sometimes.
The trick's in retrieving them it seems