Most CG stations are severly overloaded. They are not there to take your routine float plans, and they really don't want to hear that stuff unless you are saying "This is the yacht Doubtful, our engine has failed, we are barely making headway, we are not currently in distress but would appreciate your keeping a radio watch with us, with ourly contacts, until the storm has diminished or until dawn."
As to float plans...that's something you have to decide based on the your abilities. A friend of mine was going on a week long delivery cruise, figured 7 days was optimum, 9 was allowing enough slack, and ten days meant something was preventing them from getting dlelivered. Our agreement was that I would call the USCG and report them overdue on the morning of the tenth day. Night #9 came and his wife called to ask if I'd heard anything, and that's when I called the USCG to say "He's not overdue, but they're pushing it, if I have to call you in the morning what do you need to know?"
The forms are quite a bit more extensive than you might think, if you plan to file float plans, you might ask for a set to pre-fill and leave on file.
Meanwhile, my local USCG station connected me to Group Atlantic, who connected me to the Caribbean station at their departure harbor, who said they understood but would ask to see if anyone know for sure they had LEFT on schedule. All on one local phone call!
On the morning of the tenth day I got a phone call from my friend. Hurricane detours, engine failure, tied up 700 miles south of their intended destination because that was as good as they could get.
But it is YOUR CHOICE, as the skipper, to decide when you will be overdue. In icy waters, you might want to make that a lot faster than in warm ones.
Just realize the USCG puts a lot of attention into every call--and they can't spare it for babysitting. Make sure you don't start a SAR response without good reason. And consider investing in a cell phone booster and antenna for the boat, as a way to place "nearshore" calls further offshore. Or, a SPOT device that can send an "I'm OK" message via the internet and email through satellite. Quite reasonably priced!
Also consider the VHf marine telephone operator channels:
VHF Marine Radio Channels: Use the Right Radio Channel for the Job!
It isn't cheap, it may cost you $5 for a one minute call, but as a way to say "Honey, don't worry, we're just going to be way late" that can make sense too.