I lived aboard for over two years in Hampton, VA (tip of the Virginia peninsula, near Norfolk), and continue to spend weekends aboard year-round. It gets kinda sporty in January and February, and you must be mindful of keeping the water pipes warm enough, but I got used to it. Sweaters work well.
There's a big if that has to be considered....is the boat in the water or out. As fas as winter freezing temps go, the boat is much safer in the water.
My suggestion would be to go where the boating is fun and you have things to do so you can enjoy the boat If you really stuck on the icw it will get old. The cost difference between going 700 miles or 1000 miles is minimal.
Just had a pretty good winter here in S FL. Bring it down and you get a nice place to stay in a warm environment conducive to boating. Very few days where long pants are required ;-).
My boat came from Lake Norman NC.
The guy never winterized.
Instead he had 2 bilge heaters that were set to go on at 32'.
They do get snow there, but it never lasts.
So it really depends on your prep.
If the boat is in the water, you need at least a couple of days of freezing temps to make more than just skin ice on the water. The engine room is surrounded by 35-40 (or more) degree water.
I once went to check on my boat one night when the temp was under 10. Inside my boat was at least 20 degrees warmer and since the boat was in a covered slip, it wasn't the sun that had kept it warm. It was the water it sat in.
The key is look at what states do insurance companies have freeze damage waivers. Boat US (Geico) waives for FL, GA and SC. So if you boat does have freeze damage in those states, you are covered. The thing I find is a boat in the water gets a lot of warmth (or lack thereof) from the water. Water temps in my area rarely drop below 45 degrees, even when the air temp is well into the teens which only happens for a few days.
I believe you are thinking of CA. Inland areas of CA lake boating can get quite cold. For FL, northern and central FL can get very brief frosts / freezes. Most too short to bust things. In South FL, frosts and freezes are not an issue.
Last year or the year before, 2 guys that I work with had the blocks of their I/Os crack because they did not drain them. Both were on the trailer. I never drained mine, but with the boat cover on and a 100w bulb in the bilge when it was going to get down in the 20s I was OK.
I live in Charlotte NC, and most winters a boat sitting in the water would do fine without winterizing. My previous boat (SeaRay 290) sat in the water, I kept a boat safe heater in the bilge. There is at least one cold snap each winter that could freeze things. Currently my boat is dry stacked in an unheated building - in 5 yrs it's gotten to freezing maybe twice inside the building. I winterize. I think Charleston SC and south a boat in the water is not a worry - except that once every 10yrs winter event that surprises everyone. But don't be fooled, Charleston is not a tropical climate they have seasons and winter can be cold - relatively. You really need to go to south FL to get completely out of the freeze zone. The problem with the south is not that we get these hard freezes, it's that we are not equipped to even handle a moderate freeze. I have heat pumps, and a night in the teens and they can barely keep the house warm at all. Remember just a few winters ago - 2010 I think - there was a point where snow was on the ground in all 50 states.
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