"Launch and go" may not be totally crazy even in winter!
The two big considerations are:
1) Is the boat fit to go?
You can ask the local USCG Auxiliary if they can stop by to do a courtesy inspection
. If there's anything unsafe or lacking, they'll tell you. If everything is OK they give you a big gold star (OK, just a blue sticker) to put on the boat. Either way, there's NO penalty if anything is lacking.
If the boat seems safe, reliable, well equipped, take it out for an hour or two on a good day to see if that's really so. And if it is...then Boston to the east end of the sound is not a big deal. I'd want 2-3 crew with me, but they can also usually be found. (Along with towing insurance
and a working VHF
and cell phones.)
2-Some good weather
. I know, it is cold out today, but this is not going to be a killer winter
. Either plan for a warm couple of days, or put on appropriate cold wx gear
and take cold wx sleeping bags.
It won't be a Sunday cruise
...but for two grand? Hell no, unless there's major work
to be done on the boat, sailing or motoring it down should be something to think about.