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Farr 11.6 (Farr 38)
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I sail on the Chesapeake almost year round; pretty much any time there isn't ice between my dock and the Bay. I do dress with multiple high tech and wool layers. Like others have said, I wear an inflatable harness, and I rig teathers and jacklines. I keep a change of clothes and lots of blankets on the boat. I also try to make sure the decks are clear of ice and typically won't go out in temps below 40 and dropping since spray can freeze on the deck making moving around unnecessarily dangerous.

But as others have said, winter offers some of the most beautiful sailing of the year with clear blue skies, seasonal wildlife, no traffic, and good winds. Probably one of the best cruising months on the Bay is the month of October. In late October, the flyways are packed with geese and the autumnal foliage is in full magnificence, the breezes are good, the temperatures are not too bad, and the anchorages are wide open.

One other point, the water remains comparatively warm well into early to mid- November, but the can be deceptively cold well into late spring due to the snow melt to the north of us.

Jeff
 

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+1 to what Jeff said:

Jacklines, tethers and harnesses. Spare clothing and blankets.

Also, the ability to boil water for instant soups and hot beverages. Hypothermia doesn't just happen when someone falls in the water. It will happen when you're bone-dry as well. Hot beverages help combat that.
 

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Sailed most of my life on Lake Ontario and I'm new to sailing on the Chesapeake Bay.
Our season upnorth last only from end of May to late Sept, maybe Oct, depending weather and early snow.
We now live in Va and sailing out of the Bay near Deltaville. For the entire month of July and part of June, everytime we go out, there is very little wind, if any at all. Is this normal for this bay, and if so, how long does it last?
That really reduces your sailing season.

thanks
Patrick
One thing you have to get used to is the depths! We're Lake Ontario sailors too and you get used to the depth sounder reading in hundreds of feet! Not so in the chesepeake! its REALLY shallow! freaked me out constantly when we chartered there this summer. You also have to get used to the crab pot floats! they're everywhere, specially where they are not supposed to be! like channels, harbour entrances, etc!
 

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One thing you have to get used to is the depths! We're Lake Ontario sailors too and you get used to the depth sounder reading in hundreds of feet! Not so in the chesepeake! its REALLY shallow! freaked me out constantly when we chartered there this summer.
Welcome to the Chesapeake. An old proverb[sic] 'One is a lair if one hasn't run aground at least once in the Bay..':D
 

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Josh, Jeff, and BubbleheadMd,

Thanks so much for all of your responses. –Will definitely look into getting jacklines, tethers, and harnesses. It's so frustrating to think sailing is over when it's just really beginning in the Fall. It's such a beautiful time of the year to be out on the water. This weekend, particularly Saturday, looks to be a great day on the Bay! I will show bf your responses and hopefully he will agree :D .
 

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Sailing is definitely not over.
A trip to Bacon Sails, and a Saturday of drilling and epoxy will get you setup with jacklines and tethers.
 

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Sailing is no where near over.

Looks like the fall winds kick in at least Saturday. From a distance a rocking ride for us down the Bay....Maybe to Rhode...or is it still full of the cruisers?

If not maybe to the Narrows then through them to the Wye
 

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Sailing is no where near over.

Looks like the fall winds kick in at least Saturday. From a distance a rocking ride for us down the Bay....Maybe to Rhode...or is it still full of the cruisers?

If not maybe to the Narrows then through them to the Wye
Rhode was packed last weekend thats for sure.

We opted to anchor in the cove on the west side not far from the entrance due to the forest of masts in the more popular anchorage further up the River. Really a very pretty anchorage but a bit exposed for this weekends forecast.
 

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This weekend looks good for sailing, probably going to head over to the Chester or Wye. Yippee
 

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Rhode was packed last weekend thats for sure.

We opted to anchor in the cove on the west side not far from the entrance due to the forest of masts in the more popular anchorage further up the River. Really a very pretty anchorage but a bit exposed for this weekends forecast.
Yeah agreed about the openess. All options in play include Aberdeen, Dividing, Granary, et al. Would like to take advantage of the push.
 

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We're new to the Chesapeake too, thanks for the information. Used to sail in northwest Lake Michigan: nice winds but...season that started Memorial Day, ended in October at the latest. This is better.
 

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Re: Yup, can be a problem.

pdq,

Nice web site.

We are thinking of heading to the Chesapeake area end of next year or early the following. Will be reading your area info.

Greg

a. You now have a 12-month season. Spring and fall are best for cool temps and dependable wind.
b. We watch the forcasts a lot, looking for wind, not avoiding strorms!
c. Reaching chutes are great.

On the otherhand, it is unusual too have too darn much wind in the summer, except for passing squalls and the very rare huricane.

My blog, listed below, has a bunch of Chesapeake stuff on it. Enjoy!
 

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Someone say they where looking for some wind on the Bay..?

Coast Guard rescues 3 people, a cat and a dog near Cape Charles, Va. | Coast Guard News

Plenty yesterday..

Side note..I wonder what type of anchor they where using when they reported it dragging...Fortress??

6 lousy miles from a safe harbor.

They could have run south under bare poles with the engine idling, and busted a U-turn into the Cape Charles channel and bashed their way under engine, into the harbor. The breakwaters at the harbor would have tamed things enough to make the final right turn into the harbor calm enough.
The channel is narrow, but there is some wiggle room just outside the marks.

The other less appealing option, would have been to make a hot beam reach under a scrap of jib to Hampton Roads. Once out of the fetch, and in the lee of Old Point Comfort, things would become more manageable.

The best option would have been to make note of the forecast, and not set out in that weather at all.
 
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