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We also have a family of 5 (kids are 13, 11 and 6) and the previous boat was a 25ft trailer sailer. We stared looking in the 35-45ft range and my present boat (LOA 44ft) works well with the kids forward and us aft. We are also finding that the kids want to bring friends along so we often end up with 6-7POB's for weekends. We are looking at 2-3 week trips, so given your shorter timescale a 35-39ft boat would probably work well. A boat just under 39ft also fits into a 12m pen.
Ilenart
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