For many years I always stepped the mast with the boat on the trailer, but in the last year or so, I've been stepping the mast with the boat on the ground and I think I really prefer to do it this way.
I slide the boat off the trailer and onto the beach wheels so the wheels are about under the rear crossbar. Then spin the boat so that the stern is pointed directly into the wind, hook up the mast step (note I keep the aft mast stand on so the mast is supported at the back side before raising), and raise the mast.
The advantages I see for raising the mast with the boat on the ground - Can easily point the sterns directly into the wind to reduce cross wind effect on the mast.
- The mast is lower to the ground by several feet so again less windage.
- The crew supporting the back of the mast is now able to hold the mast several feet higher relative to the boat, so it's at a much better angle for beginning the lift.
- With the beach wheels under the rear crossbar, the boat is naturally in a bow-down position so gravity helps hold the mast up once it's raised.
- The forestay/bridle wires are at a more manageable height for the crew to connect them.
- Less stress on the hulls due to rear trailer rollers.
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