My opinions - Weekender VS Vacationer. Basically they are the same boat, just different sizes. Both are pretty neat little unballasted sailboats that don't take a fortune to put together, although you CAN spend a bunch on them. Using reasonable materials, you should be able to create a Weekender,minus trailer but with sails, for in the vicinity of 2K$. They are NOT open water or offshore boats, but are designed for protected waters and seem from reports I've read, to sail very well although they are NOT gonna climb up to weather like a fin keeler:) The Weekender seems to be a great size as a daysailor or over nighter for someone with a backpacker mind set. Not a whole lot of room in either the cockpit or the cabin. Should float in around a foot of water, sail in just over two feet.. The Vacationer is larger and has enough room in it for a several night trip.

My wife and I could camp aboard a Weekender for several days - both of us are smaller people. I'm 5'8", 165 and she's 5'2, maybe 100 lbs. We could probably spend a week or so aboard a Vacationer.

I don't think the Vacationer would be that much more expensive. You should also look at the Pocket Yacht. It's a small boat about the W.E. size, but cat rigged- has more interior.