First, let me say welcome!
Having traveled Winnipesaukee over the last 50 years in everything from a rubber boat to the MT Washington and a whole bunch in between I will echo what has been said with a few more details.
Assuming decent weather and a chop of 1 ½’ or less I personally find anything that is as VitaBene says is a true 21’ hull up to the mid 20’s to be a good all-around boat for this lake provided it has is a deep V hull and a decent gunnel height. Obviously bad weather/high wind is a game changer and in that case ONLY size helps!
An example a poor Winnipesaukee boat is my 20” Glastron/Carlson ski boat which really has an 18’ bottom, a very soft V hull and super low gunnel height (at rest I can reach over the side from the drivers seat and touch water) This boat is super fun during mid-week when no one is on the water and there is no wind. Add a good breeze and typical Saturday summer traffic and you get beat up real quick in this boat.
My current boat is a 23’ Caravelle Interceptor cuddy. It is not a full deep V, but decent, and the 23’ does not include the length of the swim platform (which would make it like 25’ – 26’). So far we like boat this a lot, but it was a compromise from what I wanted, a 26’ Wellcraft Excalibur. We opted for the smaller boat to save a few dollars, to make trailering easier (I do not leave my boat in the water) and because with every foot longer hull you get, the boat becomes a bit more difficult to maneuver around the often crowded Winnipesaukee docks. (something to give consideration if you like to visit the many towns around the lake). The 26 Wellcraft would surly have been a better bad weather boat and offered a bigger cabin, but for 90% of our usage, the 23” does the job quite well.
I would also strongly advocate a cuddy cabin boat over a bowrider. I personally HATE having people riding in the front, it really makes me uncomfortable with the many poor drivers we see these days. I also find that having a place to store personal items, to change if needed, and just to get out of the sun. Its also a good place for a porta-potty, which can a life saver with a family. The is also the perk of another place lounge as the front deck allows you to stretch out and not have others climbing over you all the time as when on the read deck.
Well that was probably more than you were looking for. We have our most fun finding a sandbar and dropping anchor and breaking out the floaties, or maybe some light waterskiing or tubing, so our 350 Magnum power is more than enough. Don’t get me wrong, I like a big honkin motor as much as the next guy, but just don’t make any use of it these days with young kids, busy weekend traffic, and speed limits, so use caution blowing the budget on big engine options.
Oh and last item, make sure you get a big bimini top, its almost an essential with a family and if you want to spend any serious amount of time on the water.
Best of luck with the shopping, it’s a lot of work, but look at as many boats as you can before pulling the trigger. Money being no consideration the Chis Crafts look GREAT! Just way over my budget,,, (someday,,,)
Hope this helps, ATB - GH
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