Jeff, are you going to leave it set up on a beach or have to trailer it? The reason I ask, stepping the mast is a job and not one a 5yr. old can help with. I started in mono's too and then switched to cats, my first was a Hobie 18 with a rolling jib and I took my then 6 yr. old son out with me all the time. The rolling jib came in quite handy when it got too windy for both sails. The only draw back to a Hobie 18 is you will have some trouble righting it if you are alone on it.

I later moved to a Nacra 5.5 which is also a great boat, lighter, faster than the Hobie 18 but the mast stepping is just as hard and really requires two of you (will your wife be with you to help?). The Nacra 5.5 is harder to find and will probably cost you more as well. The Hobie 17 is nice too but also hard to find a good one, cheap. There is a classified link over there on the left.

The Hobie 16 has been the boat of choice for beginners for about 40+ years and is a great place to start, just be aware of the pitch pole potential when you are on a hot reach. Then once you figure out cat sailing, you can trade up to something bigger and faster, and your son will be bigger and more able to help as well.

And be sure you get Rick White's "Catamaran Racing for the 90's" even if you don't plan to race, there is LOTS of good stuff in there and is considered essential reading for any beach cat sailor. Click on the store link at the top of this page to order it.