Are you an experienced boater? and in the size and type of boat you are renting??
If not, I would not consider it, Winnipesaukee is not the best lake to start your boating experience on. Maybe try Winnisquam, I think a good size pontoon on Winnisquam is a safer and more enjoyable outing for a novice.
In either case, beware that most boat rentals outfits no longer offer insurance, so if you hit anything you will pay the full price for the repair and maybe even lost rental time. So carefully read the rental contract.
If you are experienced boater, and committed to boating on Winnipesaukee, I personally suggest you stick to the south side of the lake. Get a map first study it and find the spots you want to see, and only go during the middle of the week!
If you start at Meredith, you can visit the Weirs, Lake Port sandbar, cruise by Governors island, then down to the West Alton sandbar, hop over to Wolfboro, down to Alton town docks, and then hopefully a nice safe trip back to Meredith and it can all be done in one long day. Or any subset of those locations.
Alternatively, you can also hire a captain and a party/pontoon boat and they can show you around, and help you build a sense of comfort before you try it yourself. A good captain would make the trip very enjoyable and safe, and its a good way to transition to making the trip yourself.
Hope you find an option that suits you, and have a safe and fun trip.
ATB
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