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On the Wind Sailing

'On the Wind,’ is THE podcast about offshore sailing, where professional sailor & journalist Andy Schell interviews sailors from around the world to discover what inspires them in an effort to inspire you! Andy has interviewed everyone from legends like Sir Robin Knox-Johnston, to tech gurus like Nigel Calder, boat builders like Magnus Rassy (of Hallberg Rassy), inspirational family sailors like Totem, YouTube stars SV Delos & Andy's personal favorite, Arctic sailor and octogenarian Bob Shepton. Thanks for listening & hold fast!

Jun 7, 2016

#150. is my good friend, sailmaker Chuck O’Malley. I’ve worked with Chuck and his business at Chesapeake Sailmakers since first moving to Annapolis after college in 2006, and he’s been my sailmaker ever since. Back then, I was living on my dad’s boat Sojourner, and Chuck repaired a spinnaker we had onboard. He’d eventually build all three new sails for Arcturus before our Atlantic crossing, build my dad a new mainsail before his first Caribbean 1500 on Sojourner, and is currently finishing up the two new genoas that will complement the new Hydranet mainsail on Isbjorn.

In this episode, recorded at the WCC Ocean Sailing Seminar weekend in March, Chuck discusses the technical aspects of building and maintaining ocean-going cruising sails. It’s the second or third time he’s spoken at our events, and his talk is yearly surveyed as a favorite among seminar attendees. Chuck talks about design and construction characteristics; downwind sail choices; three-reef versus storm trysail setups; storm jibs; gennakers and Code 0 sails; and much more.

Before we get to this week’s show, a quick little update on Isbjorn. We’ve changed our schedule for the remainder of the summer, and will return to Annapolis from Newfoundland in August, instead of crossing the Atlantic as planned. Mia and I are realizing that delivering the passages to the high-level that we strive towards is a lot more stressful than we’d anticipated. Having to cross the Atlantic twice to get to the Caribbean in time for our 2017 program was just biting off more than we can chew. We’re learning the hard way that with ocean sailing, stuff doesn’t always go to plan, so we’re changing the plan. You can read the full backstory about the changes, why they happened, how the new plans affect our crew, and what’s in the future on our most recent newsletter at

With the changes, we’ve got some new opportunities to sail with us. July 25-August 4th we’ll be sailing south from St. John’s, Newfoundland to Chester, Nova Scotia, just outside Halifax. It’ll be a combination of cruising and exploring ashore on the fjords of Newfoundland, with some offshore, overnight sailing down to Nova Scotia. It’s new grounds for us, so will be a real adventure. Then, August 4-11, we’ll depart the Halifax area bound 600 miles nonstop for Annapolis. We’ll also be sailing south again with the Caribbean 1500 in November, and have added 2 Caribbean passages to the calendar in early 2017. Go to for the updated calendar and to register.

Also due in part to our schedule changes, we’ve added a few events to the schedule. We get lots of emails from friends and fans in the places we’ll be sailing - if you’re in the Lunenburg or St. John’s area this summer, give us a shout and we’d love to show you around Isbjorn between trips! If you can make it to Annapolis in the fall, we’re hosting another Open House aboard the boat on the Friday of Boat Show, October 7. Finally, on the weekend of October 21-23, I’m hosting another Celestial Navigation workshop in Annapolis. It’ll be $500 and limited to the first 12 people to register. Go to to sign up!