NEWBIE: Cost-effective power boosting (21ft Wellcraft/Merc)

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I've got a Wellcraft Elite 210 (wooden swim platorm) with a Merc 225 IO. A friend said he can get one of his streetcar racing techs to "bore" the engine "out" to yeild a good amont more HP out. Is this true? My manual says my transom can handle up to 300 hp. Is this the route to go on my limited budget? Sould I let a car guy deal with a boat motor? Can anyone recommend a boat tech to do the same?
Any other fairly cost effective power increasing methods to get to 300 anyone can think of? CMI exhaust/manifold? High-performance heads? Bolt-on Blower?
And how about the prop? Can someone recommend the best type and pitch for power? I'm less interested in off the line speed with 2 people on board, and more interested in top end power for 6 women and 2 kegs. Right now I'm so underpowered in the marina I whale and drift as if my prop wa in trailer position.
Thanks in advance

[Craig]

Merc 225 IO, is that a V-6 or V-8? I know Merc has a 220 horse 305, what year is yours? Just boring a motor 30 or 60 thousands over won't yeild a "good amount of horsepower" You'll get a small increase in power because you pick up 5-10 cubic inches, but not enough to justify just boring the motor alone. Typically you bore the cylinders to true up the walls. You get the power from raising the compression. If you do have a V-8, I'd concentrate on exhaust, intake, carb and maybe camming. Experment with props as well. If you end up using someone else to do your work, you'd be well advised to go to someone familiar with the needs and tricks of a marine engine, not a street car guy. As far as shops go, you might checkout offshoreonly.com. there are a bunch of east coast guys that hang out over there and might be able to recommend a shop.
Craig

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Thanks for the advice.
To answer your question it is a 5.0/220 V8.

[twistedpair]

With 6 women and 2 kegs onboard, who cares how fast you can go!?!. People will slow down to party with you if necessary!
What kind of prop are you running? A good stainless prop and thru hull exhaust are good relatively inexpensive (this is a boat, after all) places to start.
Welcome to the board! :)