A lot of good advice here so far.
Think very carefully about how you will use the boat. Will you trailer it or moor/slip? Do you need a tow vehicle? Do you have kids/family needs for the boat? New vs. used.
Each person will be different, I can tell you what I did. I live on the South Shore and spend a lot of time in Truro on the Cape. I have little kids and limited time.
I chose an 18' Center Console. 4 years used, Grady White on a trailer. Easily towable, launchable, solo handling, and storage (garage). Relatively low fuel costs. My experience has been good, going into my 4th season.
I find that CC Bay/Stellwagen is rarely calm enough on the few days that I have available to me, for offshore use. While the boat can handle 2-4' seas, it is not pleasant and I just don't bother. Going out in 1', fishing and then coming home in 2-4 is a different story... I'm not sure this would be any different in a 21' CC for ME.
I have learned a lot about boating, fishing (very different from surf casting), and how I might use a larger boat, without breaking the bank. The GW 18' is a big boat for its size, very capable. No problem running from Scituate to PTown on a good day.
I personally feel that in order to get alot more usage in the conditions we have, I would need to jump up over 25'.
One more thing as it relates to kids, if applicable. My kids love the open bow of the CC and have never missed a small cabin. With a smaller boat, 18-23', you need to hold the little ones when underway at any speed in any kind of seas or they bounce around. So for me, a cabin is not of much use in the smaller boats.
I would say a 20ish foot boat is a good starting size. Go used with a late model year and you'll save $$.
Enjoy the process, its a lot of fun.
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