No need to worry about the 5 foot waves unless there is a strong north west wind. Winter Harbor is a great area & is perfect for tubing as you are not on the broads(the largest part of the lake). There also is less traffic especially during the weekdays. Wolfboro is very close to Winter Harbor so no trouble going to the town docks there.
Weirs Beach is no problem for you in your boat from Winter Harbor as long as the chop is not too high. Just check for that strong north west wind I mentioned earlier. I recommend you go on a weekday though as its very crowded in that area on weekends especially during July 4th.
Don't worry too much about it being rough. I know the area you boat in Essex well as I have boated the North Shore & Cape Ann for many years before coming to Winni. The lake is mild compared to what I have experienced in that area. I did alot of boating off Plum Island into the Annisquam & launched in the Merrimack in Newburyport. Its a great boating area.
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