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I'd go a little larger, if you have the experience to handle a larger boat. 26-28' can be a little tight for a family of four, even for a couple nights.

A larger boat is also likely to have air conditioning, which could make a big difference that time of year. When we chartered a couple years ago, we thought AC would be totally unnecessary, but there was one hot, muggy, stagnant night where it made a huge difference. We rented a slip to get shore power and were very comfortable.

We used Haven Charters in Rock Hall.
 
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