Look at local
MacGregor sailboats (22-26). Really easy to sail. They all accommodate a
head and have overnight capacity. And best of all, there are lots of
cheap, almost free boats available.
They usually come with a
trailer and a small
outboard and are easy to move around. They sail well in light air and can be sailed safely even if the
wind and waves pick up. The swing
keel means less to worry about in shallow
water and having the real
cabin provides a level of flexibility and
safety. And these boats have positive foam floatation, so they won't sink if you happen to fill one with water.
Whatever you get, be extremely careful with the young one. Crap happens on any boat, especially while
learning. And it often happens quickly. Easy enough for an adult to lose their footing and go
overboard. Recovering someone in any kind of
wind is a challenge, let alone a child. Even with practice (a good idea), it can take 10-15 minutes to get someone back on board. So try to leave the little one at home until you feel comfortable on the water.