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Re: Going up the mast
I just went up the mast on our 28' sailboat for the first time a couple of weeks ago...had a bosun's chair and was winched up (two halyards). From what I understand, it is tough work winching up. Fortunately our neighbor was in his slip, as my wife certainly would not have been able to do it. It is a bit nerve racking as well as the higher you go the boat certainly rocks a bit with all the weight up there - but settles down...and as calm as the day may be, once you get up there it will certainly start to pick up!
If winching, I would suggest hauling yourself up on one halyard while the slack is taken up with the wincher below...