It CAN be done, but it is easier with 2 people alongside a pier. If you need to do it alone, the best method that I've used (on my DS II) was to launch the boat, bring her into a beach, pull hte stern up on the beach, then take the mast...put the lower end of the mast in the cockpit resting against the cuddy bulkhead, now walk the mast up to vertical, and now the tricky part..... while holding the mast vertical, step up onto the cuddy top and then carefully lift the mast up (keeping it vertical) and guide it towards the mast hole in hte deck, carefully lower it down through the deck until you feel it hit bottom, if you carefully move it around you should be able to find the step (metal fitting that the mast fits over to hold it), carefully lift just enough to get the mast onto the step and let it settle onto the step. Now attsch shrouds and forestay and adjust.
No, not easy....... actually, it seemed easier before I tried to explain it! I mostly get at least one person to help me when ever I've stepped my mast this way, a second person inside the cuddy helps to get the mast onto the step, a third can help lift and keep the mast vertical. Finally, this method will work for a DS II, but will need to be altered for a DS I (no cuddy bulkhead).
You may wish to post this question on the Day Sailer Class Association forum on their web-site (
www.daysailer,org) I'm sure someone there has come up with a neat solution!
If your trailer is pretty stable (my boat rocks too much on hte trailer, despite proper bunk adjustments) it may be easier to do this on the trailer. Check out the video posted on YouTube by Cape Cod Shipbuilding, showing the way to step the mast on their BULLSEYE sailboat (they also show stepping the mast on the Day Sailer, but it is a newer one with a hinged mast). I'm amazed as I watch Gordon Goodwin easily step the mast on a Bulls Eye, he makes it look too easy (his age is around 70!)