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If you decide to go out, keep a SHARP lookout for logs, escaped docks, steel drums, shopping carts, bodies and don't get complacent. I'm not planning on doing any night sailing for a while, either. If you do, have a lantern that someone can use to sweep the water and warn of debris.
Here in the PNW, we ALWAYS have to keep a sharp lookout for debris in the water. The tidal currents create long lines of "drift" where you can find anything from sea foam and kelp, to logs and floating trash. While not as bad as it was years ago since fewer log booms are being towed up and down the Sound to lumber mills, there is still plenty. There is never a leg of any trip here where we don't have to divert around pieces of wood or logs that are large enough to cause potential damage to the prop or rudder.

So, I'm not sure sure that would keep me from sailing in the Chesapeake, just keep a eye out.

Dave
 

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If your boat can't hit a log or floating debris (logs, trees, etc) without being in danger of being holed and sinking, then you need to buy a new boat. The trouble with the typical "bay boat" is that many are not really sea worthy. They are constructed for typical bay weather...light, thin hulls, light rigging (masts, etc), relatively low displacement, etc, and when ocean type conditions arrive, they fall apart. We like to go out in 20-30 knot conditions in our fast, but relatively bullet proof 60's fiberglass boat, and I wouldn't let a floating log intimidate me. Check out a recent trip last Mother's Day: Varsity Sailing - YouTube
No one said anything about sinking, but I'd prefer to avoid damage of any kind when I can help it. I'm happy that you are perfectly sanguine about playing chicken with a floating log. Me, I'd rather keep a sharp eye out to avoid hitting them. Just because something is "bullet proof" doesn't mean you should shoot at it.

Dave
 

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Can someone please explain to me how bay sailing is any less demanding on a boat than ocean? I have been in some pretty rough weather in Cape cod bay, buzzards bay and now the Chesapeake. All of the places have some pretty severe conditions. I would rather be out in the open ocean in 30kts than the lower chesapeake with a 30kt NE wind!
Not I.

I sail in the protected waters of the Salish Sea. The only truly rough stretches are the Strait of Juan De Fuca when the winds are coming in from the Pacific at WNW or Georgia Straits when wind and tide can conspire to create some nasty conditions. That is all deep water however. I'd not like to be in the wind waves created in the Chesapeake Bay by high winds. Same holds true of some of the Great Lakes. Where I'm at, there rarely is enough fetch for winds to create much of a sea.
 
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