I suggested we sail around a bit and wait for the winds to fill in a little more consistently before attempting to sail her into the basin and the slip. Now I've sailed into the same area with a Rhodes 19 or Ideal 18 but that was different given the size of the boats and in those cases only sailed up to the dock very slowly to tie her off. This was going to be different in that it's almost 30 feet of boat and it was sailing her into her slip with lots of other expensive boats around to sail past. Basically it's like parking along a curb with the smaller boats versus parking a bigger boat into a parking space at the mall with all the other spots occupied. I admit I was a bit uneasy.
I felt the best thing to do was preplan the best option and maneuvers that would make it successful, anticipating everything the boat would do based on the feel and winds. I suggested we sail as close as possible to the concrete walk way of the Pier and Gybe so that we had a straight shot into the basin past the break wall. Just about that time there was a bunch of traffic coming in and out of the entrance, but since we were under sail and moving at a good speed, it went smoothly. Once in we waved another sailboat past since they were under power. I moved forward and dropped the jib into the forward hatch. Once we sailed past the first line of docked boats we headed up towards our row of slips. I warned that the main would Gybe as we turned into the row and about half way up the row I dropped the main sail since we were coasting along at a good speed. I coached Jessie from the bow to slightly turn into her slip, close enough so that I could hook her dock lines and pull us in.
All in all, the sailing in went textbook and not even close to any dangerous mishaps with any of the other boats. It was carefully planned out, thinking a few steps ahead and anticipating what the boat and sails would do at each point, coaching from the bow and no tense raised voices that is often heard from boaters in unfamiliar situations and conditions. Jessie did well at the helm coasting her in as I instructed from the bow.
This is definitely not something I'd like to do all the time but it was rather rewarding to test my skills of planning, expectation of response from the boat and making it happen flawlessly. I couldn't have been happier with the outcome and neither could Jessie since it is her baby.

Here is a photo kind of explaining what I'm trying to describe by tight spaces.
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