Friday the 13th nightmare!

Jesse, a friend of mine, asked me to help him sail his 46 Morgan down from Treasure Island to Boot Key Harbor. This is the story and it's a woozy!
April Friday the 13th, I should of known better, I jumped in a 10 seat twin prop and flew from Key West to Clearwater, FL. What a ride, it was exhilarating, zooming amongst the clouds. Little did I know this was just the beginning. After landing Jesse and I went to the s/v Island Gypsy. She was a mess! There was no way he was prepared for us to leave anytime soon. We took the next few days to organize, stow and prepare the vessel for our voyage. We installed winches, cleats and the bow rail, organized tools, parts and food. Jesse assured me he had taken her out a week earlier and the mechanical systems were working. I noticed many flaws I would have fixed if she were mine. Most importantly she only had one lower shroud on both sides of the mast. But I was not going to spend the next 4 months in TI fixing her up.
The next morning we moved his 22 foot Shamrock Towboat from TI to St. Petersburg. This vessel is a center console work boat, similar to a skiff. At one point we got into 6 foot confused seas, a yucky ride to say the least, I probably would have lost my breakfast if I had had any.
Tuesday around noon we picked up a lady friend of his at the John's Pass fuel dock. We hailed the bridge tender and off we went into the Gulf.
The 6 knot winds and 3 foot seas were directly on our nose. We motored until we passed the Egmont channel. Then raised the canvas and turned into a close reach. My first realization of trouble was during this process. I asked Jesse "Which one is the topping lift?" He looked at me like a deer in headlights. I replied "OK, the line that attaches to the end of the boom.". Then I asked him "Which one is the main halyard?", same look...I replied "The one that pulls up the main sail.". Then he jumped on the bow and attached the jib sheets, brought both ends of the jib sheet on the outside of the shrouds on the same side, not through any of the blocks and wraps it around the winch. Not the way to hook things up!
About 20 minutes later, POP goes the starboard lower shroud straight for my head. I ducked just in time and screamed "Into the wind!" We dropped the main and Jesse went below to get some parts. Up he comes with...... Chain!? After fumbling with the shroud for 10 minutes it's temporarily attached..... by Chain!?... He now wants to put the main back up. After long deliberation, of me explaining the physics of sailing and rigging, and him telling me it doesn't matter, his lady friend pipes up and says "Let's not put it up" so he left it down. Thank God! My belief is, we would have lost the rig if we flew the main. Boys and girls..... always have your full rig up before going sailing!
A little time later I looked into the companionway and saw smoke. Jesse ran into the engine room and screams "Shut her down!". Now I'm sailing a 46' Morgan with a tiny jib in 4 knot winds, on a close reach. I look at the GPS and we're going 1 knot sideways. 20 minutes later Jesse gets back behind the wheel and sarcastically says "Check it out." I go down into the engine room and look at the alternator. He rigged up the belt so that it was working, but it wouldn't for long. I congratulate him on his Macgyver skills but questioned him on spares. He continued to explain how he has many spares aboard, just that none of them are for this boat. So we need to find safe harbor and gets some spare parts, quickly. Luckily, New Pass isn't far, he said he has been in and out of that pass many times and knows it like the back of his hand. Boys and girls..... always carry spares, for your engine, before leaving port!
About an hour after sun down, roughly 9pm he turns Island Gypsy towards the channel. We pass the outer marker around 9:30. However, a few days later I would read an article from 2003, which stated the Coast guard removed the markers from New Pass because it was too dangerous to navigate.
I feel her bump the ground and encourage Jesse to put her in neutral. A few seconds later she comes to a halt. Now, when this happens to me, I put the vessel in reverse, back off the shoal and find a new way. Well... Jesse decides to gun it straight through the shoal, full power. There we were with an 8 foot draft, full keel sailboat dredging a channel. Come to find out she has a new 45 hp VW diesel engine. Way underpowered for a 46' Morgan! All I can think of at the moment was "I'm givin' her all she's got Captain!". To no avail, for the next 30 minutes I attempt to get Jesse to turn around.
SMOKE! The rigged up alternator belt broke. We inspected the engine room. Not only was the smoke thick but there was a lot of water in the bilge now. We inspected further, the bilge pumps were no longer working and water was pouring in through a hole the size of my thumb, from the stuffing box. Jesse rewired the bilge pump and put line in the stuffing box. We turned all power off except the bilge pumps and tied on some webbing to replace the belt. All is back to normal except that we're in 4 feet of water with an 8 foot draft sailboat. After all this, the Captain decides we'll rest until morning.
I took night watch, grabbed a blanket and took a nap in the cockpit. We were taking 3 foot waves to our port aft for the next few hours. Around 11:30pm I was awoken buy a few drops of rain hitting my face. The sprinkles stopped, but what happened next alarmed me once again. 20 knots of wind out of the SW started blowing. I knew the full fetch of the Gulf would produce 6 foot surf within 30 minutes. I alerted Jesse, we put out a Bow and Stern anchor and waited. Sure enough, in came the 6 foot waves, they were beating us up pretty good but they were still hitting us on our port aft.
After 20 minutes of 6 foot waves crashing on the stern, Jesse comes up with an idea. Let's cut the stern anchor rode and the waves will swing us around. I argue that all that will happen is we'll end up broad side in the waves. I begged and pleaded, please don't cut the stern anchor. He goes out anyways, and sure enough he cuts the stern rode!
Within 5 minutes we were taking 6 foot rollers right to our beam. Slamming uncontrollably side to side. Each wave would slam us twice. Once to the port as it came and then starboard as it slammed us. The noises the boat created were duplicated in only the scariest of movies. We had radios, black bean cans, tools, parts and pieces flying throughout the craft for what seemed like an eternity. As us sailors say "She puked all over herself".
All night while getting thoroughly beaten up, I kept looking to shore. Wondering is that beach or rocks the waves are hitting? I mean, come on now, I'm pretty sure at this point Island Gypsy is down for the 10 count. I hoped for the best but prepared for the worst. I put all my things in a dry bag and waited, well actually I held on for dear life.
Around 7:30am the sunrise was gorgeous and the waves subsided to 3 foot rollers again. It's a beach... and it's 200 yards away! Around 8:00am Jesse informed us that the rudder post put a hole in the bottom and we were taking on water, time to abandon ship. Everyone begins grabbing there things and heads to the cockpit.
We put the 12' aluminum dinghy in the water on the leeward side. Tried one outboard motor...it didn't work. Try the other motor...it didn't work either. "Guess we'll have to row." I exclaim. Jesse replies "I don't have any oars". 'WHAT?????'. We ended up using some wood trim that we found as oars.
All night long Jesse's lady friend had been a real trooper, joking around all night while staying upbeat. I grabbed a life jacket and put it over her head and fastened it. She, all of the sudden, becomes distraught and hesitantly proclaims "I can't swim!". Great, I'm thinking, can anything else go wrong? I jumped in the dinghy and used all my might to keep our current rescue craft at the side of the Morgan. Jesse's friend get's in, followed by Jesse. The first couple waves hit us on the stern, no big deal.
Then, a 3 foot wave hits our rear quarter and swamps us. Jesse's friend screams "My medicine!". I jump in and start grabbing bags. The next wave flips them in the water. Jesse hollers "We can stand!". Jesse's friend stands in the knee-deep water and exclaims 'Thank F.....G God!" which is followed by a wave that knocks her down. All three of us then began moving towards a fishing boat. It was waiting for us in some deeper water. We jump in and got onto land within 10 minutes.
Once on landed I called Julie to come pick me up. She then started the long 6 hour haul from Marathon to come and get me. Grandma Rosanne and Grandpa Wally thankfully live in Sarasota, so I hung with them until she showed up. I was so exhausted, hungry and thirsty, it was a very somber day indeed.
Many lessons where learned by all that day, especially me. Always carry spares and only an inflatable dinghy with oars is exceptable as a lifeboat! I personally learned many more lessons than that of course on that day, but I'll keep that discussion to happy hour!