• Do you stay overnight because you are sailing a long course (greater than 1 day trip)?
Yes and no. Sometimes it is because we planned a multi-day sail and sometimes it is because we just felt like anchoring out. It may be overnight or just for lunch and back to the slip. I know someone who leaves his dock and anchors out about 500 feet away, just to get away from the slip.
• Do you anchor out, or come back to a marina?
The way we use our boat, we can stay out two nights depending on how hot it is before all the ice melts. Then we find a marina to purchase ice, fill the water tanks, etc. One of the clubs we sail with has two cruises with one night at anchor, one night in a marina. Another club we belong to prefers to anchor out as long as possible.
• How big is your boat? How big is the cabin? Can you stand up in your cabin?
Old boat: 22 feet, could not stand up.
New boat: 30 feet, can dance an Irish jig standing up.
A 70-YO man in our sail club has a 19-foot boat that he takes all over the Bay and anchors out in it in all types of weather. His wife stopped going with him so he finds a sailing partner (usually of the same age).
The reason I ask this is because I always dreamed of doing this. We bought our first boat (the Merit 25) and tried an overnighter at the marina, and it was anything but relaxing.
Two adults, a child and a large dog would not be my idea of fun in a small boat. All of that on a hot day, not on your life.
We kept our 22 in a slip and it rocked and rolled at the slightest wake but we slept well. As long as we kept supplies to a minimum, we had enough room to stretch out below.
We want to do this, we really do, but we had a bad first experience!
Then you'll find a way. It may take some compromises.