Here's a lesson learned from my first careening experience:
We tied to the careening pole on a high spring tide. Each successive high tide was lower. That evening, high tide was 8 inches lower than the morning's, and the next morning's was a further 4 inches lower.
Although being high and dry was great for scrubbing the bottom, that evening, despite our finest efforts, we did not get off the pole as planned. Further, we knew that if we didn't get off in the morning, we'd be stuck in front of the Dinah Beach Cruising Yacht Association for two more weeks.
That night we did everything to make the boat lighter; we dumped our water tanks, moved our fuel and water cans onto dry land, and lowered our anchor and 200 feet of chain into our dinghy. We hoped this loss of weight would help us float a little easier and slide off the careening post.
With high tide approaching, we ran our longest Panama Canal line from the stern to the wall, cranked it tight, and watched the water rise. At high tide, we began pushing, shoving, and rocking the boat to try and get her off and floating.
We were not successful.
We squared our backs against the careening pole and with all our might, leg-pressed the boat past vertical and rode it down until it was floating on its starboard side. Alan hopped in the dinghy, rushed to the far bank, and put all his weight on the main halyard.
This didn't quite work, but it did create quite a scene, thus leading to a fellow yachtie named Peter to join the fun. He drove his truck over to Alan and tied the halyard to the bumper.
With Alan and Peter at the truck and Amanda and I putting extra tension on the stern line, we slowly bobbed and slipped back into deeper water!
We ended up putting on quite a show for the members of the Yacht Club, I just wish we had set up the time lapse camera that morning.
So, if you're ever going to go onto a careening post, only go up as far as you need to.