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Learning the HARD way...
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I helped a client bring their boat from RI to VA in 2019, we left on November 6. It was way too late, as we had wind against us all the way down Long Island Sound, and we froze. It didn't help that the boat had a non-functional diesel heater. When we arrived in Atlantic City, NJ, it was sleeting, and when we left the temp was 23ºF. The dinghy on davits had about 3" thick ice frozen in the bilge.

I brought my boat from RI to the west coast of FL in 2020. I left on September 26, and had a (mostly) glorious trip south. You can read about my experience here: Finding a new home?

There are organized groups that head south every year, but I wonder why anyone would want to join them. I have never done so. The thought of traveling with, and having to compete with, the same people for slips, moorings, or anchoring spots does not sound like a good time to me. "I like Sailing and Beer ⛵+?...and maybe 3 people."
 
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Learning the HARD way...
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7,699 Posts
Hi,
I see your point. This being my first trip south, I was hoping to buddy boat. I sailed solo this far.
Good crew will help make this enjoyable, and safer. You WILL meet people along the way (if you are social and you want to). You don't have to travel the whole way with them, nor would I want to do so.

I found crew through the gosailingapp.com website.
 
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