12:21 a.m. on March 2, 2013 (EST)

Eye candy? 18.5 feet of WW-1 vintage Old Town Otka
The wheel is made of 2 wicker baby carriage wheels. The other 2 wheels were made into another wheel for another canoe.
While i don't think a kayak or a canoe would work well for the trip some points to see may assist.
I made the steering and I made the sail from 1926 pillow ticking, because it was what i had. The battens are paint stir sticks and while it was 1984 when i made the sail I still have it today. The key is getting it dry. Ain't that just the way..... :-)
I still have that 'Folboat' aircraft alloy mast too, but it is no longer the mast I use, which is now spruce.
There are 3 lines visible. the center most is the halyard (haul yard) which raises the sail. The other 2 lines are shrouds or in this case back standing stays, and are used one at a time to windward.
The red boards are ply wood just hack waste and scrap and were painted a zillion times, known as Lee Boards, and the down wind side is the one that should be down, and if your scared they can both be down.
These are mounted on a oak dowel about 2 inches thick, which the wheel is mounted on, and 2 bronze cleats are also mounted on to hold the shrouds.

This of course was a shot taken years ago as well. I was over taking a larger sail boat and running from what turned out to be one hell of a hail storm. A women in the larger boat came to me as i was tying the last Lashing over the canoe on my car asking if I might like a picture.
This is what she sent. She says her husband said i was doing better than 17 knots. She said, her husband said, it is impossible to plane a rounded bottom canoe, and that i was exceeding hull speed!
Just leave it to me to break the laws of physics. The best i can say is i was scared... I was really scared, and this is the wind that caused the shrouds to come to be.
I also own 3 rudders in the bottom of this lake, and assume all 3 are still there. This sail is 63 sq feet and it is all the sq feet that are safe. I have capsized once in all my years, and dunked the gunwhale once but was able to save it with out being totally swamped and awash.
Now if it were me doing this trip there is no canoe or kayak I would consider but because of the 500 pounds of gear, and the fact sails would be used.
My choice would be a lapstrake design by Chappelle called Swampscott Dory. It would have a drop down center board in a boxed case which thwarts (seats) would brace the boat to be stronger.
I have more pics of this boat, but none in the water. The reason I placed this pic is you can see it is a more sea worth craft and it has a feature known as Tumbleholm which makes it as stable as a dory get get. The more you heel it over the more stable it gets.
I must say i tend to agree with Erich alot. I am new here as a day ago so I don't know anybody.

I lied here is one more shot, so you can get the idea of the difference. And this boat is also 18.5 feet long but far more boat and wider. You could deck this over several ways.

This boat has a wrap around stern seat, a center thwart and a fore thwart and 2 storage areas, one foremost and one at the stern. In this shot the fore deck bulkhead is open and shows as black, a shadow. The hatch cover is standing on it';s edge on the forward left in the boat.
The tan object is a the dagger board because it can be removed completely, as a table. It is lead weighted so it was a heavy table.
I did attempt to sink this at a fresh water beach in 5 feet of water, by pulling the drain plug, and having 150 pounds of pure lead placed in the bottom. That wasn't enough weight to sink it, and i was out of lead.
The reason for that was i wanted to know if it was a safe boat, and how much weight i might have to not worry about. In another time and place that boat carried a bronze gun that weighs 45 pounds, and Lake George is better than 200 feet deep in some places ;-)
The idea of dying in cold water, under gray skies has never been very appealing.