gwood -- as many have said above -- you'll be just fine in an 18' jet boat.
The answer to your question of Sally's Gut -- is that it is a narrow "passageway" behind Stonedham which is a Natural Preserve Area that you are welcome to explore (hike).
As far as tubing/skiing -- most anywhere will do mid week. The waters (weather-wind dependant) are usually quite calm most midweek days before say noon.
I would not hesitate to venture anywhere on the Lake with your 18 footer as the others have said -- Wolfboro is a great take and easy ride (mid week) if the weather permits and will give Mom and the kids another shopping area -- head out of Merideth by 9-10AM and plan to spend the better part of a day on this trip!! When our kids were smaller we use to have them alternate skiing on the way over. To give you a feel for it -- at a comfortable cruzin speed (not knowing the Lake) it will take you 50 minutes to an hour, one way -- without sightseeing -- which you'll obviously be doing -- also NOTE the "Witches" on your map, behind Govenors Island before you start (and don't let them scare you away from the trip)!! As someone above mentioned -- even with just "wind chop" the ride back always seems longer and bumpier so be prepared (time wise).
Finally, another area that is fun to explore by boat are the "Islands" - have your map handy and run around "Mark, Timber, Round and Camp Islands". There is a no wake passage between Mark and Little Mark that is fun to run through.
My only word of caution is to be completely comfortable reading the navigation sticks (red - black) and have a compass aboard before you head out past Merideth Bay.
Don't be bashful Explore !! You'll love it !!
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