Yours should be located on the thermostat housing....starboard side. Yes, it probably can be done on the water. It all depends how much access you have to the engine.
If you tilt the engine up all the way, you should be able to do install the nipple without a lot of difficulty. You will then have to route the tubing through the grommet (where all the cables are going through....unfortunately, that is where you would have to remove the cover that retains the cables.....there are screws and bolts that like to jump into the water. You have to cut a small access to the hold in the grommet for the tube to be pulled through....then you have to route it up to your helm and the water pressure gauge.
Personally, if I were going to be on the boat, I would want to be on the water and save the work for after the boat comes out of the water. Just my opinion.
Mike