The wife and I headed out for an overnight at Cat Island. It was blowing 15-20kts on the way out. Same all night, and next morning. After 2 days, things were picking up! Storms predicted that pm, so we knew we had to go, or stay. Motoring out of the cove in my 22 footer and 4.5 merc was iffy. Making 1-2 1/2 kts depending on if the prop was in the water or not. Motoring into wind/ waves I wondered what would happen if I turned her abeam to it. Wife asked what I had planned and I said didn't know! It was maybe her second overnight. She managed to keep her into the wind and I raised the jib. Immediately the boat stabilized and I realized this was very doable. Sailed on that tack until almost DDW to harbor. We flew back to harbor, with waves coming under the boat and surfing. The wife was looking aft, saying the waves were above the stern rail. I was looking forward and watching them come under the boat and away. Awesome. I had plenty of time to contemplate the age of my sail, rigging, etc.! Wind had increased during the 2-3hr trip, and at some point I realized that if I could not keep the prop in the water at cove, I surely could not just head upwind, drop sails, and motor in like Sunday driving. I had entered harbor/slip under sail once before, in benign conditions (5-7kts). Oh well, better chance of survival inside the breakwater than out. I sailed it like I had stolen it, navigated the channel and breakwater, then tacked toward my slip. I intended to round up, drop the jib, and enter slip. I mis-calculated and did not round up enough. The sail filled and we shot down the slips, 5 ft from all those boats! Nothing but concrete awaited me at the end of the pier. Managed to round up and get sail down/ into slip with no damage to myself, boat, or others. The wife had not been enough, and I had not instructed her on lowering sail. This would have helped. I was busy at helm. Looked back at data, and it was blowing 25-28kts with higher gusts as I approached harbor. Maybe 5-6 footers. In a larger boat, or even one with an inboard, it would not have been that big of a deal. With a 22 footer, swing keel, and cavitating outboard, it was a bigger deal. All's well that ends well. And the wife went back. All good. Living and learning in MS!