Sailed to Green Island with a mate once 27 Km out, then back about 54 Km round trip. A fair few guys here have done it over the years.

Only recently Dr Cam was sailing at Green with too big a sail and too small a fin, couldn't get back up wind to the island after a downwinder so he just gave up and headed to Clifton Beach (coast) on his own, over 30 Km away

Not a sail board but likewise a Hobie 16. In San Diego, I told the 2 friends with me we might see some whales, (on the horizon). We brought a few (too many) beers with us and other "intake-ables". Beautiful day sailing, sailing sailing.... then a noise and the smell of cat food. Whales were all around us. We "oohed and ahhhed" in wonderment. We headed back and as the sunset paddled the last kilometre back to the beach. The next day I thought about how dangerous that was, but am always glad that I did it, (and made it back safely!). Oh to be young and stupid!!!

I was sailing on lake macquarie this morning - 100m offshore and couldnt see land in any direction! Got a shock when the other side of the lake loomed up out of the dust.

as you say, a very rare thing and very memorable.
I almost whimped out of going out on the lake today for that reason.Years ago i was sailing in a thunderstorm up at Myall Lakes with no visibility due to rain.I must have been doing 25kts + & when it cleared I was only 50m from shore & heading straight in ( shallow). I decided not to do that again.

About 18 years ago sailed out from Sempahore SA to round one of the Outer Harbour Channel Markers on a '9ft Wild Catz' slalom board and I think a NP World Cup Race 6.0m (first of the monofilm sails). Made it to the channel marker, gybed around it, and then looked up and completely shat myself when I saw how far I was from the shore.

Then SNAP! uni joint breaks off completely. Oh ****. It was Christmas eve too, and my mind started to race about how this could pan out badly. Then I had a McGyver moment. I had excessive down haul rope, so I unwound the excess (left the sail tensioned of course) and threaded it under the deck plate of the uni that was still screwed into the board. I threaded this through and around a few times, and back up and through the pully area near the tack of the sail, effectively making a rope universal joint.

I was able to water start with it, then slowly plugged my way back. After a few hundred metres I had one foot in the straps, then a little later the other foot in too. In the end I was hooked in, and planing back to shore with my rope uni working very well.

I made it back slightly downwind of my launch. That experience has stayed with me, and I always consider my distance from shore now when sailing.

1km past Morton Island from Wello with a couple of mates 15 years ago, 25km's out.

Nick Maloney crossed Bass Strait, and Alison shreeve attemped it earlier in the year, its 240km.

My first sail in WA at Leighton don't know how far out i was but my boom broke,sailed back in clew first and ended up a couple of k's from where i launched,the real worry was that i didn't know anyone so nobody would have missed me

I've done 160K's non stop in the ocean JP but no more than a few K's out at the time.