We too live south of Boston, and we have rented the past 5 years in different spots on the lake. We trailer our 20' Sea Ray with a cuddy cabin. It's is 27 years old and still runs great. So I'm all for Sea Rays even though a Grady White walk around is my dream.
I never thought of getting a slip and staying on the boat the whole time. Lots to consider doing it that way as previously posted. Has it's ups and downs.
We are actually downgrading ours, hubby has a sweet deal on a slightly used Bass Tracker so he can take it out more places near home without having to trailer the bigger boat. The only time we seem to use our boat is the week we spend up at Winni. We did take it out on the ocean and down the Charles river many times but I really hate salt water. And there aren't any decent size lakes without traveling an hour or more. I personally am not thrilled about having a boat without a port a potti and I do not fish so I don't think I'll be on the other boat other than the week up Winni, so nothing changed there for me.
Also make sure you know what your doing. Being new to boating with a big boat can be tricky. And Winni has many tricks to it. I always study the Bizer map prior to vacation so I know what's near where we are staying. I broke the prop last year. Thankfully hubby is handy and could put a new one on.
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