My second boat (first 'big' boat) was a Newport 28. I was looking to move up from a Catalina 22 to something my family of 5 could spend weekends on. The Newport 28 was great for day sailing: easy to handle, capable of handing 25 kt wind and 6' waves, spacious, etc.
It was fine for a night (and OK for 2 nights) for my family (wife, daughters 11 and 8, son 5), and everyone had a bed. The problem was there was no room for gear when we were in 'sleeping' mode. By the second night I was tired of stepping over gear, moving stuff from the cabin to the cockpit, and otherwise having very little space. If you can tolerate those conditions for the length of your trip, then a 28' boat would work for you. The good things about 28' boats is that they are affordable, you can definitely find a good boat for under 20K.
For me personally, when I wanted to start spending a week or so onboard, I sold the 28 and bought a 35'. The extra length and width and interior space makes spending a week aboard very comfortable.
In 28' boats I like Newport (obviously) o'day, Sabre, Tartan, and a few others. Catalina 27 is very affordable, but may be too small.
Deep Blue C, 2002 C&C 110
Mt. Sinai, NY
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