So it has undeniably become autumn (or winter) and the cabin on the island is closed and the boat needs to come up on land. I'm not too keen on spending 5000 on a 30-trailer that isn't available closer than 75 miles away. Therefore, I'm considering if it can be solved in another way, especially since we don't have a tow hitch on the car.

Scenario:
310 kg boat in the form of a Crescent HT 418 plus 60 kg outboard needs to be taken out of the water and then rolled 200 meters to the storage location. Concrete retrieval ramp.

Hardware:

Two of these boat supports
http://www.clasohlson.se/Product/Product.aspx?id=22712899

Four pneumatic rubber wheels 260x85 mm (max 200 kg each) plus axle steel.
http://www.clasohlson.se/Product/Product.aspx?id=20058982

Some kind of winch. Partly to get the boat onto the trailer and partly to get the trailer and boat up the ramp. The latter winch will also be used for tree felling.
http://www.clasohlson.se/Product/Product.aspx?id=15083910
http://www.clasohlson.se/Product/Product.aspx?id=13226366

Do you think that with this material and some sturdy beams (45x145 or 170?) it's possible to create a construction that will last at least one season? I'm planning to weld a retrieval trailer next year if I gain access to welding equipment. Or should I just go to bed and hope I get a better idea tomorrow?
 
My suggestion is to call 5 friends and carry the boat by hand the short distance!
 
It comes down to several things, but mostly that the boat is located 32 miles from our home.
 
It should certainly be possible to build such a cart.
I have had one for a long time, albeit for a much lighter boat, but still.
As long as you get the geometry right, you shouldn't have any problems with such a light boat.

I had some issues over time with the wheels. They tended to rust, probably because I didn't grease the axles often enough.
Perhaps a system to inject grease with a syringe might be a good idea?

The wood in my cart has held up well. It's about 18 years old now.
 
See no problems at all with building it out of wood. We're talking about maybe a maximum of 450 Kg, which isn't very much.

One option would be two 45X170 on edge. On top of these, you attach the boat supports. On the underside, you place two lying pieces of 45X95 per axle. These are nailed together at the back. At the front, make a center hole and put a piece of threaded rod or a carriage bolt through. Don't tighten too hard. Voilà, you have a turnable front axle. Just need to make a suitable drawbar now. If you happen to have an ATV or something similar, it will be really fun :)
 
No problem. Go ahead and build. You have an easy skiff.
 
It will be absolutely excellent!!
 
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