there is a rig in Bill Mason's "Song of the Paddle" film available on VHS
from the National Film Board of Canada or borrow from some public
libraries, of two canoes lashed together with poles, and a A-frame mast
also made of fresh cut green poles, using a spinnaker sail. A spinnaker is
light weight nylon suitable for packing on a trip. I looked on the Internet
within the past year and saw them second hand for about $200 US.

These days I don't know how practical it is to count on being allowed to cut
poles to use for the mast and the beams connecting the boats together.
One of the challenges is designing a rig with short light weight spars you
can carry with you. I've played with the idea of using the tent poles
because you'd never be sailing and sleeping at the same time.

If you want good performance there has to be enough open water between
the two canoes so the waves produced by the hulls don't interfere with
each other. The rule for catamarans is the width has to be at least half
the length. So if you want to sail two 16 ft canoes as a catamatan the
keels should be at least 8 ft apart.

If the wind is from behind or a bit to the side there is no need for
daggerboards sticking down into the water to keep the canoe-catamaran from
sliding sideways. If you want to sail crosswind or upwind you'll have to
have daggerboards or use spare paddles. Unfortunately daggerboards are one
more thing to carry on a trip which would be no fun on a portage.

Don't try putting one sail on each canoe to sail upwind as one sail will
always get dusturbed air wind from the other and make it pretty much
ineffective. One sail is best.

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