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I have a classic Montauk and, to be honest, I think it is way too small for a family of 5 regardless of the kid's ages. A Montauk is a great 2 man fishing boat and is OK for two couples to ride in. The lack of storage space means towels, floats, tubes, life jackets, etc all have to be stored either under the console or in the bow anchor locker or left out on deck. Montauks are open skiffs, they are not family runabouts or ski boats. The pilot seat will hold 2 people in relative comfort and the cooler in front of the console will seat 2 more in tight quarters.

For a family of 5, I would look more to a Dauntless in the 20' range.