I have a spade rudder that CAN be taken out in the water as the rudder stock
goes through a tube that finishes above water line, but I wouldn't risk it and I
think you really should put it on the hard. It will be much easier to do the job
plus you can check the hull where it's scraped.

Yes, providing the tube that the rudder shaft goes through is undamaged - and the top is above the water line - it should be possible to remove the rudder with the boat still in the water. I did it with my cat, after snapping one of my rudders in half (photo).

I found that the biggest problem was the buoyancy of the rudder making it difficult to pull it down. I solved the problem by tying rope around the rudder so I had something to tug on. Having a hookah was helpful too.

sunycoastguy said..
Went to go for a sail on weekend and notice sturn anchor wrapped around rudder and bent it.
Now rudder scrapes hard on bottom of hull
Are rudders easy to take out, can it be done in water or will i need to take boat out
Any advice would be appreciated

I removed the rudder on my old M&W26 which is similar to your Holland. I made a net with weighted bottom edge and slid it over the rudder, released the top nut and let it slide out {my rudder tube went right through to the deck]. Most rudders will be full of water and just sink. I did mine in the middle of winter. This time of the year I would shift the boat into shallower water and just remove it there.

Thanks everyone for the advice, i think I'll take my chances and do it in the water as i dont have much steering to get it to a dry dock as it is
Although the outboard motor in the well will come in handy for a bit of steering, I'll let you know how i go