Without the captive mast setup, I suspect the only practical way to step the mast would be a dead lift. Stand the mast up in front of the front beam, stand on the tramp and lift up and set it in place, you would have to have the shrouds and forestay VERY loose. Sounds dangerous to me......

I have the captive mast base and raise the mast my by myself. Try to park with the front of the trailer downhill if possible. If it is real windy, park with the front of the trailer downwind and let the wind assist you. (That also helps to keep the mast standing in place while you fasten the forestay.)

Position the mast on the tramp and put the back (top) of the mast on a 6' stepladder. Slide the mast onto the ball (mast is lying on its side) and insert the pen into the captive mast base. Make sure shrouds and trap lines are clear and will not get caught on anything. The mast will continue to lie on its side. You may want to make sure the shrouds are slightly loose or you may not be able to attach the forestay to the bridle. Make sure that the forestay has a clear shot at the bridle and will not get twisted/tangled when you step the mast.

Attach a long line to the end of the forestay and run it through a block attached to the winch post on the trailer. From the block, go under the bridle, coil the remainder of the line and lay it on the tramp. (This line will have the forestay/bridle in position and will help keep the mast standing when you leave the tramp to connect the forestay.)

Now get on the tramp and put the tail of the line that you attached to the forestay and stick it in your belt/pants. From the very rear of the tramp, with one foot on the rear beam to get good support, lift the mast (not really all that heavy but it is somewhat awkward) and get under it as quick as you can. Lift and go hand over hand while walking forward, as quickly as you can, to step the mast. Quicker is better. While doing this; try to keep the slack out of the line that is attached to the forestay. Once you get so far, the side stays will keep the mast from going side to side. If you were able to park with the front of the trailer downhill/downwind, the mast will practically stand on its own.

Holding tension on the line, step off the tramp, attach the forestay to the bridle, remove the line, remove the pin from the mast base, tension the shrouds and go sailing (after putting away the ladder, which I bungie to the trailer).

Terry