Rudder leaking

Just tighten it first. Don't need to pull the boat. Small leakage doesn't mean you need to repack it. It's easy to do but if you haven't got the tools or experience, let a mechanic do it.
 
Very easy to tighten...if you can get to the packings easily, and there is some material left.

Given you location and age of the boat, it would be a good off season project to repack them. Its pretty easy and cheap. I have purchased large wrenches from Harbor Freight Tools to do the job.

Google rudder shaft repacking, there is a great youtube video on how to do it. and there are several threads on here as well.
 
If there is room to tighten it down, just do that. 1/4 to 1/2 turn is all that may be needed. You can repack in the off season if necessary.
 
Loosen the top nut to break it free, then spin the bottom lock nut down a couple turns, crank down on the top nut a turn and then bring up the lock nut to lock it in place. Don't over tighten, just snug it. Here are the best tools. The York wrench is nice. I keep them both on the boat.
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