The second a boat touches the water, I check the bilge before I trust anything below the waterline. Then the engines go on and I walk straight to the stern to confirm cooling water is pumping out. Two checks, every single time, before the bow ever points offshore.
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Offshore, your whole job from the dock to the destination is managing risk. The best sailors don't rush. They see what's coming first, then commit. Ryan's got tons of pearls of wisdom.
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A mast over the side isn't dead weight, it's a battering ram that can hole your hull in minutes. Save the boom if you can, but cut the turnbuckles and get the rig off the boat.
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