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So felt pretty dumb today after I took my boat out for the first time and thought there's no way I'm the only guy who's done something silly out there so let's have it, the good bad and the ugly....something for us all to laugh at as we head into another long winter.....ok me first

In my defence I've never sailed before this summer, but bought a boat, took some lessons on a better boat and then decided to fix mine up. Re worked the trailer, new tires, paint and bumpers, then Painted the deck and sent the sails for a wash some other general stuff here and there. at some point I took the transom flaps off and decided not to put them back....looking at the old ones I didn't think they did much anyway and just assumed the transome would be above water and it would be a non issue till I got around to it. Nope, all wrong, rigged the boat just how they showed me, launched it with the wife, jumped in and we started taking on water.....a lot of water. Decided discretion was the better part of valour and turned around after 20 ft . While I was holding the boat to the busy dock A guy with a camera came buy, chuckled, took pictures , and to add insult to injury loading the boat back on looked like a small circus act with my wife trying to back the trailer done the ramp. Bad first day.....lots of lessons learned.
 

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A perfect day!
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Always check your drain plug...in this case, transom flap, when trailering. What kind of boat?
We all do something once...hopefully just once
 

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A perfect day!
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I did that once with a Chrysler 16. Fortunately, my boat was still on the trailer in the ramp when I saw the water. Just pulled out and let it drain, then put in plug.
 

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My first boat was a Venture 21. After a couple of sails with friends, I decided to take my wife and two kids for an overnighter at a near-by lake. As we were putting the mast up I gave my wife (now ex and maybe you can guess why in a minute) the headstay to hold while I freed a snag on the backstay. Then I heard a quiet "oops" as the mast came down knocking me off the cabin top and into the cockpit. Luckily not off the boat and trailer. Nothing broken, but it put a slight bend in the mast. So off we sail for the overnighter. Next morning, there's a thunderstorm blowing in and we're a couple of miles from the take out. So I start the trusty 4hp outboard, turn to crank up the centerboard, and hear putt-putt kerplunk. Motor's overboard in 30 feet of water, wind's kicking up, and I start to get more than a little concerned. And a little ashamed. Put up sails, off across the lake with the wind gusting hard, and family stowed in the cabin with life jackets on. I did do something right. As we neared shore I jumped off, took a line ashore, and walked the boat the 300 yds to the takeout ramp.

I was happy to have made it back using what little skills I had and still relish the many lessons learned in those 3 exciting hours. SHE never went sailing again. It's been long enough I can tell the story with a grin instead of a red face.
 

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i should add my first overnight experience , but first ..
5 or 6 weeks ago we bough a 20 footer . had our super sailer neighbour take us out for 4 hours instruction outside our bay . NEVER SAILED BEFORE lets remember this !

next weekend my wife and i decided to sail from our bay up to a spot called Skotfjärden ( Siarö sundet ) its a 3 to 4 hour sail if you know what your doing ..
we set out . motored out into the main channel and it was dead calm . we fiddled around with the sails and finally had about 5 knots of breeze.. we had a "broad reach" all the way to Siarö Sund. made it in 4 or 5 hours ,.. ahh now to motor to the overnight camping spot . all was a joy . later that evening we had a bottle of wine and amazing food .
we were feeling like this was going to be easy to learn to sail ..

next morning 100% sun at 25C just perfect . laying around on the deck and making food , swimming . now its time to make our way home .
motor back to Siarö sund from the camping place. out in the main channel and looked south and the sky was just BLACK and you could see rain squalls in the distance , exactly where we were going . the wind was picking up FAST and the water was now white capping and a couple meter waves . the weather was deteriorating fast.. everything was going well ( motoring ) until we decided it was time to put up the sails .
we put up the main the then jib .. shut the motor down . and all hell broke loose . basically we were over powered and lost control over the boat and sails and were heeling over 45degrees ( felt like 90degrees ) when i couldnt control the boat i instructed my wife to take down the sails . first the jib went down ,but. i was nervous as hell and forgot to start the motor . when my wife was fastening the jib to the bow pulpit the wind shifted and grabbed the main and spun the boat around 180 degrees .everything in the boat was now on the floor or on one side of the boat ..
after we finally started the motor and took the main down we then motored for 5 hours home against 25knots of wind with gusts of much more ..

many many lessons learned on that trip . i went over and over this for days and days afterwards . about how to stay calm and focus and complete each step in a complete process .
since the above experience each time we go out sailing we have a check list and stick to that .
 

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...and you felt dumb...
Can tell you first hand, on board us navy hospital ship Sanctuary ...with 2 admirals on board, U.S Marine Corp band playing on dock...morning leaving for states after 4 continuous years supporting marines in VN....(ship docked to pilings about 50 ft. from dock)... "man overboard,(drunk from my division) this is not a drill"...lower a boat...
once in water...forgot to put in plug and could not find plug...had to beach...and lower another boat.
Band did not skip a beat.
Captain was last seen shaking/holding head on rail.
This is short version of very entertaining morning including many drunk sailors throwing
pfd's over side and another jumping in.
 
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