If you had your choice, would you rather be at a marina on north or south side of cape? I'm considering getting a place at the cape. My initial thought would be Nantucket sound, as I could fish the Vineyard as well. Which side gets the most boating pressure?
I guess you better qualify your question as to the area like upper or mid or lower cape. If you are in the mid cape area then the bay side offers decent quality striper fishing thru the summer months where the sound gets too warm. But as mentioned there is always flukin and the possibility of Spanish Macks Bonito False Albacore and all the bluefish you could want. Trailering does have some advantages...
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