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Who here has sailed with Chesapeake Shorthanded Sailing Society (CHESSS)?

Black Jack

Black Jack

Pretty Penny, Mull 30
I am flirting with the idea of moving away from the bay area and maybe relocating to a house on the Chesapeake in Maryland. Covid taught me a lot about I want for my wife and I. Things here are getting a little more difficult and costly. A path to downsizing from my house for another is too competitive, poor in choices, lifestyles very costly and now that they are building so much high-rises in Alameda and removing my much loved waterfront, our sailing ground are changing for the worse. I do know many people make it work and drive a distance to have a boat on the bay but that wouldn't work me. I would sure miss sailing here in the SF bay but there are other places where a working guy from the Bay area who must still work but not kill himself can have almost all - a house, sailboat, fair dock access close by, cruising and racing grounds and a nice community to belong.

Can someone here tell me a little of what the organization is like, what kind of boats are sailed and the people involved?
 
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I sailed with CHESS. Good bunch of folks. It is not as organized as SSS and has far fewer events that are nowhere near as well attended as our events. They're fairly spread out, too, with a good center of folks in the Annapolis area but people spread out across the 120nm between Naptown and Hampton Roads. As a young organization looking to grow, it does seem to have a certain energy... I never took myself off the email list despite moving over two years ago. I can put you in touch if you'd like.
 
talonf4u said:
I sailed with CHESS. Good bunch of folks. It is not as organized as SSS and has far fewer events that are nowhere near as well attended as our events. They're fairly spread out, too, with a good center of folks in the Annapolis area but people spread out across the 120nm between Naptown and Hampton Roads. As a young organization looking to grow, it does seem to have a certain energy... I never took myself off the email list despite moving over two years ago. I can put you in touch if you'd like.
Click to expand...

That is kind of you.

My son enlisted in the Navy last year. He is being stationed in Norfolk. I can see my wife wanting to be closer to him. I am exploring the options but do not want to give up all that we have here.

I was imagining a simple small boat 28 feet or so kept in Hampton Roads would be a ticket. sail there, see the son and race in the years to come.
 
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