How to prepare a boat and trailer for overlanding

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Flipper

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IMO I would take the engine off and everything out of the boat and strap it down. I would think twice about changing tires because trailer tires are not the same as vehicle tires. WD-40 your leaf springs and lug nuts. I carry a extra hub/bearing kit and 2 spares. Make sure you have a jack that works with your trailer.
 
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VI Overlander

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Is your trailer equipped for off road? The lakes we frequent often can’t accommodate a boat trailer so we have never invested in one. I can throw my 12’ smoker jon on my little Jeep trailer but it gets a bit wonky with the length of the boat and the RTT.

for me when I think of “overlanding” it’s often off pavement as much as possible but more so it’s about burning mileage and not setting up base camp. So in terms on that I would make sure you have adequate axle clearance and good bearing and such as said in previous post.
 
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Billiebob

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The lakes we frequent often can’t accommodate a boat trailer
This ^^^ there are no real boat launches once you are overland bound.

And I agree, don't leave the engine hanging off the transom if you are actually overlanding.

A picture of the boat hooked up would help. When you say "work" boat, what is that, a welded aluminium boat with a jet drive or ??