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"How We Think About Sailing" // Annapolis, MD // $50pp

  • Federal House Bar & Grille 22 Market Space Annapolis, MD, 21401 United States (map)

“How We Think About Sailing” Panel

Andy will host/moderate a panel discussion on exactly what the title implies! Join us before you head across the street to Boat Show for a thoughtful chat on offshore sailing. The panel will also be recorded for the podcast, and there will be ample time for audience Q&A afterwards.


Meg & Morgen from Ocean Racers
John Harries
of Attainable Adventure Cruising

…and a legendary ‘mystery guest’ to be confirmed shortly. You won’t be disappointed ;)

All the panelists (including the mystery guest) are former On the Wind podcast guests - have a listen to their episodes to get to know them before the discussion!

"How We Think About Sailing" // Annapolis, MD // $50pp
68 available

To sign up, click the ‘Register Button’ above. Next step is to go to the ‘cart’ and follow the steps (on the computer, you’ll find the cart top right on the website).


You can learn how to sail anywhere, and there is TONS of info online about how to outfit a boat for offshore sailing (specifically on, run by panelist John Harries). We’ll touch on those topics, but I want to dig deep into the different personalities and perspectives of our panelists and talk more about their distinct sailing philosophies. What can we learn from the vast and varied experience of our guests, and how can we apply that to our own plans and dreams? A few of the topics we’ll deep dive on:

Leadership styles
How an offshore racing sailor thinks (and how we can apply that to offshore cruising)
Fear, anxiety & emergencies
Decision-making under stress
Seamanship & weather forecasting
& More…

I feel strongly that we cannot, and should not, tell YOU how to go offshore sailing. We can only speak from our own experiences, including our successes and failures, and it’s up to you to learn from it.


  • What: Panel discussion moderated by Andy & recorded for the podcast.

  • When: Sunday, October 13, 10am-1pm (with short break in the middle). Go straight to the Boat Show afterwards!

  • Where: Federal House, behind Market Space in downtown Annapolis. Private room upstairs and right across the street from the show!

  • Who: Max 75 people. Chance to meet and mingle with some of our sailing heroes.

  • Why?!: Because no matter our experience, there is always more we can learn.

  • Price: $50 per person, which includes coffee and some basic brunch-time nibbles. Tickets are nonrefundable (but you can give it away to a friend).

59º North Swag

Come to the panel representing 59º North with some new swag! Order in time so you can show off your support at Boat Show.