What was the sailing moment you will remember forever?

SF Woody Sailor

Super Anarchist
100% agree.  The Jubilee was outrageous.  You couldn't walk 15 feet up Cowes High Street without bumping into yet another long-lost buddy.  I remember seeing three Kings with the Aga Khan walking up the street togethe in reefers to the RYS in deep conversation and laughter.  

Racing in a fleet of 38 (yes, 38) 12-metres was very special.

The grand ball at Osborne House (Queeen Victoria's mansion) was a bit good too.
I agree that the ball was better than ordinary. It wasn't easy to find a place to get my dinner suit pressed on the Isle, but that is a different story.

Many of these things (knockdowns, sunrises) are vivid, spectacular memories to be cherished. I have a library of my  own. Wire guys on a Petersen 44 that looked as if they quite deliberately intended to kill me still haunt me.

However, the Jubilee was something that didn't occur prior to my lifetime and won't occur again in my lifetime. So I rank it #1. At one stage I remember them doing an auction of a vertical of bottles of Hennessy Cognac for every year from 1851 to 2001. One hundred and fifty bottles of Hennessy Cognac from each year. My recollection is that Bill Koch won in the low digit millions.

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3AM on a Cal 39 surfing waves on the delivery home, watching the speedo creep up into the teens, it was like riding a roller coaster.  Went down below to make some coffee and was fallowed by a wall of water down the companionway.  Heard the owner laughing a big deep belly laugh and looked up to him standing at the helm looking like a drowned rat with water up to his knees and the lazarette in the cockpit.  Asked him if he was good, and he replied "I've been hearing voices anyway and then something tapped me on the shoulder, and then I was all wet, yep, i'm good, but I'm all wet."

Doing 18-25 knots on the Farr 400 down the Chesapeake for 8 hours, specifically the last 10 miles of blast reaching with three of us huddled together on the rail, hoods pulled over our eyes laughing our asses off getting firehosed but hauling ass and knowing we would get in before dinner service was over.

The first time I ever felt a keelboat start planing.

Losing instruments and navigating by compass and lightning strikes on a night delivery.

Pulling into Newport at sunrise.  

Too many to share... 

Like others have posted there are so many, but I will list a few:

Learning to sail as an adult in a 420 with my wife.
Adult learn to sail lessons at our local yacht club.
We were avid canoeists and hiking out reaching gliding through the water effortlessly was a LOT of fun for us.
We still have pictures from this hanging on our wall at home 15 years later.

First long distance delivery, midnight in the center of Lake Michigan with no land in site, glass calm lake, no clouds, no moon, star filled sky mirrored in the lake.  Forever hooked on night sailing.

2011 Chicago Mac, sailing through the big storm to win our class and finish 3rd overall.  Watching that storm approach was an unforgettable light show.

Cruising the North Channel of Lake Huron for the first time with my family we had 2:
Getting a very close look at a Tornado.  It was the first time in a long time that I was scared on a boat.
Waking up in the middle of the night while anchored in "the pool" to listen to the wolves howl.

Handing the helm of my 35 ft boat, sailing with the kite up in a race, to my 10 year old son and watching him sail the boat the last 1.5 miles around the last mark to the finish line.

I look forward to making my list of memories longer each year.



Best, Doing a double handed race with my dad at like 14 and taking home a bullet.

Second, Taking my kids out for our first ever family sail, wife driving, sitting on the rail with my kids.  


So many.  Early 90's, cold Sunday night racing the Bayview to Mackinac on my 1-ton. Tucked under the Canadian Shore just flying upwind.  The northern lights started and gave us a constant dancing curtain for more than 6 hours.  Could not get anyone to go off watch.  




Super Anarchist
De Nile
First sail with friends out of Bayfield Wis. Damn that waters cold!

Sleeping on my first boat for the first time, waking up to snow on the deck and a flock of sparrows on the lifeline

first "sail" across SF Bay from San Leandro to Brisbane. Damn that bay seemed HUGE after 3 years on Lake Pepin

First sail around the Farallones

Surfing my Express 37 from Santa Cruz to Monterey

first 3 generation cruise on the delta

the gybe at diamond head (20+ knots of boatspeed and gybing during the surf)

Watching my girls first day of RYC Jr Sail Program

watching my daughter win silver fleet at Nationals last summer



Super Anarchist
New Orleans
Oh, my.... 

Well, going back forty-odd years to the mid-70s, frostbiting in Mhead in Interclubs, "wicked good" competition where no one could outspend you much, unlike in summer.  I was a pretty good also-ran, top third of the fleet of about 45 boats, where any of say 25 of them could win a race without anyone being surprised.

Mild winter day, brisk southwesterly, good crew with me, five races and doing better than usual with a couple of lucky breaks in traffic,  was in contention for the day's trophy, a glass from the MFSC. 

Last race, last beat, port-tacked in towards the right side, I really needed a header.  Wham!--we got a big one, the boat almost tacked itself, we jumped to new side, just got a foot in the strap, hiked her down as I cranked the sheet in, Zoom, off we accelerated, and crossed the two or three boats that took the middle, moving up from whatever to first.  Best feeling in the world.  And I had a good song in my head to go with it too--Roxy Music, "Love is the Drug", in the finale. 

I can still feel it, and hear it.  We won the day by a couple of points. 

A magical moment.    "Love is,  love is,  love is the DRUG!!!!"



My best memory (beside taking my wife and 2 girls out sailing a few years back) was seeing the look on my Dad’s face after we won the 2002 Ensign National Championship. He had worked so hard on his boat, crew, rig and sails that he actually sailed the best he ever had. He was 70.

We won it again 5 years later, but it wasn’t the same look. He had already experienced the feeling and the satisfaction wasn’t as visceral. It was a great regatta but winning something for the first time is unrepeatable I guess.

I had fun both times


Bull City

A fine fellow
North Carolina
1) Sailing with a friend on his Tartan 27 when the windward upper failed, and the sound when stick broke at the spreader.

2) Falling off the dock while admiring my new Alberg Typhoon.

3) An effortless 20-mile spinnaker run in my Typhoon from the Upper Keys to Dinner Key.

4) Breaking the Franco-Spanish line at Trafalgar. :p

In no particular order--

wife on wire on the hobie screaming along off of USVI on the honeymoon

20mi spinny run into mackinac isle in 75 degrees and 15kts

ripping across SF Bay under golden gate bridge on wire of the 29er

waking up in the middle of the night, in the middle of the bay, to find that the anchor dragged, when sleeping aboard off of angel island

being a couple miles west of the golden gate in the laser, by myself, in big winds and waves- very stupid, but tons of adrenaline...

first sail with my oldest son when he was 2 on his opti with him, him initially being super freaked out, then wanting to go out further and sail more


darth reapius

Super Anarchist
There are too many epic moments to choose just one...

-6 years old, standing on the side of the cock-pit on an S80 offshore which just broached in 25 knots and still had the rig in the water!

-11 years old doing 22+ knots down wind heading from Rottnest Island to Hilarys in a big sea breeze on a 44' cruising cat.

-Breaking the vang on a Thomson 7 in a 50 knot storm, and charging across the river at some un-godly speed and preparing to ditch the boat as the opposing shore approached.

-Lapping a 57' race boat at Busselton Race Week in the ol Time Raider.

-Pitch-poling my Hobie 16 when I was 17 the first time I took it out, was blowing 20-25 knots.

-First time out on a Tornado, blowing 20 knots, yanking the kite up at the top mark, hopping back out on trap, locking my foot into the transom foot-strap, watching the skipper hot the boat up, the windward hull pop and just sending the thing down hill like a bucking bronco. It was so awesome that I sold my Hobie and gave up every other OTW activity for like 5 years.



Super Anarchist
Eurocat Raid 2006. Everyone starting on starboard but we found enough room to tack out onto port - you can just see our blue sail after the tack.

Quite a buzz punching out on port  when the rest of the fleet was locked into the other tack for what seemed like ages. All the gendarmes in their rescue boats had to bail out of our way.

eurocat raid start 06.jpg



Late season 40' ex-race boat delivery from NY to Bahamas coastwise, back when I wore a younger man's clothes and had a lot less experience. We're south of Morehead City, crystal clear skies, smooth seas and 10 knot northerly breeze, so we put a chute up, and smoked along south. Debated taking it down at sunset, but the weather forecast sounded encouraging, we really wanted to get south ASAP, and "Jeez, we're making such great time," so left it up. Christmas Eve, cold and closing on Cape Fear, the wind and seas had gradually increased a bit during the day, and as the bottom came up a few miles off the cape the seas steepened, and we started surfing, pinning the old Kenyon knotmeter at 14. The boat was getting pretty squirrely, and the two crew and I all realized that the chute for sure should have come down while it was still light out...shitty moment of realization. I hand the wheel to #2 and he does fine keeping the boat from broaching for a few minutes, so I pop below to get a quick Loran fix and confirm our position and sea room, while thinking through dousing the chute. No more than 30 seconds later I hear "Oh, oh, FUCK!" and feel the boat slew around broaching, and heeling over. I fly through the companionway to find the boat on beam ends in maybe 6-8' seas, sails in the water, wind howling now that our 14+ knots boat speed has been stripped away, and both crew frozen in fear...off Cape Fear...around midnight. Sigh. Amazingly we got it all sorted out without any loss of blood, and we sailed into Georgetown SC the next day, where we drank heavily, told and retold the story, counted our blessings, and filed away "lessons learned."



The sea
Training on a short reaching course in 25-30kt of wind on a Laser. Quite a feeling and quite a sound. 

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The Q

Super Anarchist
A odd one..

Sailing down in the Falklands on Gull Island Pond, it's very big for a pond, about  half mile long shaped like a lolly pop with an Island in the top..

The week before as I was new down there, they gave me an ancient laser to bomb up and down on, the only thing to avoid were the marines, walking in one side, rifles above head walking out the other (4 foot deep flatish bottom).

 The next week I was asked to sort out and sail a Brand new Wayfarer, as they had seen I knew what I was doing.., which didn't take long. Planing single handed straight down the lake was fun..Meanwhile there was a windsufer course going on, mostly interupted by lots of splashes in the water as they fell off. Some did manage to get sailing but couldn't get back, which normally meant standing on the bottom and dragging the windsurfer back. I did relent on some and towed them back with the Wayfarer (one at a time)



New member
Lots of special days, but none better than this.  Dad's last sail.

He was a mess from the Parkinson's and the associated dementia was robbing him of his mind.  But, on this day, for just a few hours, he was the embodiment of joy.

Wish I had done this more often.

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My favorite memory has to be right before my dads Parkinson's go to the point where he couldn't sail. He always wanted to be a good sailor but didn't have the time or money to get beyond being the occasional crew, so he got me into sailing.  So I chartered us a 34' boat we went on a ten day cruise in the gulf islands.  it was great to get to give him that trip after he gave me sailing.  



Pulling into Knights Inlet on my buddies dads boat and having humpbacks jumping all around us followed by the wind picking up and sailing like mad men with as much canvas up as we dared.

That's followed by the first time I ever single handed my boat.