What it is
The boat pointed at people
The open waters of Port Phillip Bay. A base at Port Melbourne Yacht Club. And one boat. Session On the Sea brings them together and sets the course to a conversation that would not otherwise happen.
A standing Friday sail. Three aboard: Gregor and up to two guests who have probably never met, from different lines of work or life. Each brings one topic they have been thinking about. We sail, we talk, and we'll take a photo to take home. Gregor will write up a Log entry of the session in a paragraph or two.
Not a knock-off early on a Friday. It is your last meeting of the week.
How it works
Bring one topic and a good sense of humour.
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01
Bring a topic
One question or topic that matters to you — a problem, an idea, a question you have been carrying with you. No homework, absolutely no slides. Just you and your topic.
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02
Sail and talk
We talk it over under sail — if the weather permits: some Fridays are more action than talk, some are more talk than action. You may share the boat with one other guest, ideally someone you haven't met.
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03
A paragraph and a photo
Gregor writes up each topic — a short paragraph to keep and to share. You get a photo to take home — and some memories to go with it.
Why bring a good sense of humour?
I have been told I am funny. Sometimes. For a German. But that's not the (main) reason.
The main reason is the weather.
What you need
The requirements are light
To join
- A LinkedIn connection with Gregor
- A request on the booking page, at least 24 hours ahead
- Not on LinkedIn, no problem. Tell me how we are connected — or why we should connect — in the booking request
- Sign up for a $30 sail pass on arrival (insurance)
On the day
- Closed-toe shoes, a hat, sunscreen, something warm that keeps the wind out and can get wet
- A life vest can be borrowed
- No sailing skill needed. No age limit — but some flexibility is required (it's a small boat)
- You and everything you bring on board will get wet
- If the weather is "bad"… be ready to do something outdoors regardless
The season
Nine Fridays
The first season runs 16 October to 11 December 2026, numbered as sessions.
| Session | Date | Note |
|---|---|---|
| 01 | Fri 16 Oct | First Session on the Sea: one anchor, one capsize, nobody watching |
| 02 | Fri 23 Oct | 30 knots, 30 degrees, 30 topics. At least. |
| 03 | Fri 30 Oct | Two Fridays on the Bay |
| 04 | Fri 6 Nov | What is it all for? |
| 05 | Fri 13 Nov | |
| 06 | Fri 20 Nov | |
| 07 | Fri 27 Nov | |
| 08 | Fri 4 Dec | |
| 09 | Fri 11 Dec | Last before Christmas — season finale |
The Friday sail happens whether or not anyone books — an empty boat is not a cancellation.
Weather
The Session will happen no matter what the weather will throw at us — just maybe not on a boat if it's really bad. No one can predict the weather reliably on Port Phillip Bay, not even the Pros. There is nothing we can do about it. What we can do something about is how we deal with it. And we are going to deal with it. Just make sure you come prepared to spend time outdoors in the conditions of the day.
Is it a sailing day?
The reason I built the wind pages in the first place. A live read for the RS Quest, with the reefing bands and the limits for the boat — so you can see what you’re getting yourself into.
Check the wind for the Quest →This is a live reading to check on the day — not a forecast.
The Session Log
The Log grows every Friday
A sailing meeting is the way to end the week. A sail plus a published paragraph is a slow record of what people across different lives are thinking about — each with a name and a photo on it (if you are on board with that).
Your last meeting of the week
Where the idea came from: four student projects whose crews had only ever read about the water, and a winter sail with a friend and his daughter that ran from the forecast being wrong to artificial intelligence to Viktor Frankl. Three hours better spent than anything else in the diary that week — and worth trying to repeat.
Read the prequel on the Log →
One anchor, one capsize, nobody watching
The first Session went out with no one aboard but me — which, for Session on the Sea, is not a cancellation but a session to experiment. I tried to anchor the dinghy single-handed from a heave-to, a manoeuvre I have not found in any book. It nearly worked; then it tipped me, dry clothes and all, into a fifteen-degree bay — and came up anchored in exactly the spot I had been aiming for.
Read the Log entry →
30 knots, 30 degrees, 30 topics. At least.
The second Session had a crew of two, in a hot northerly gusting near thirty knots. Linda Baird — a conservation-trust CEO and, for years, our Sea Scouts group leader — opened it by text, doubting there was anything fun to talk about. There was: a reef in, the jib away, an eight-knot personal best — and talk that ran between the gusts from Scouts and education to polarisation, conservation, and a hard, unhurried look at the history of our countries.
Read the Log entry →
Two Fridays on the Bay
Back out alone a fortnight after the capsize, to do the anchoring properly — this time with cameras clamped on and dry clothes at the end. The breeze went soft and shifty, but the manoeuvre worked: anchor down, foils up, jib away, and she sat to her rode, swinging rather than dragging, as the GPS track confirmed that night. A theory borne out twice now. Twice is enough to call it a technique.
Read the Log entry →
What is it all for?
A Friday on land: three powerboat tanks to fill for sailing school and a quiet question about what all the unpaid hours are for. The answer came on the dock, from Matthew sailing in — and, before that, from an eight-year-old giving the weather briefing to a crew of twelve. Then the conversation found its own course: Ethiopia, hope for democracy, and the question every Victorian is facing — who to vote for.
Read the Log entry →