Here is G. Bailey’s FSKA report on a Mosquito Lagoon camping trip. Read the whole thing but look about half way down for "Mable, ever ambitious and optimistic " … and her tow. …
http://www.clubkayak.com/fska/tripreport.asp?trip=19
It is like dragging an anchor, don’t do it.
People seem to love little kayaks, until it is time to go overnight. Then they realize they don’t have much room for dogs, kids and a coleman stove. Kayakers always want rafters and people in canoes to take some of their stuff. A canoe is superior for overnight trips.
Not a good idea in general, although I have seen it done. A group of about 8 people used a canoe to haul tarps, a cooler, stove, etc to an island to camp. These were all seasoned kayakers with only a couple mile crossing in good conditions and on open water. They day tripped from the island.
You would not want to try this with high winds or rough water. It’s also not advisable where there is current, tight turns, rapids, or underwater obstacles or strainers. Towing a heavily loaded or wide boat can be very tiring and wind can make steering a pain. There is a danger of having the towed boat collide with yours if you have following current, wind, or seas.
I have towed quite a few boats in retrieval or rescue situations. I would never tow a boat without using a proper tow rig with a quick release feature. If something goes wrong with either boat you do not want to be tethered to another. I always carry a tow rig bungeed to my rear deck and if I am leading a trip I wear it.
Like pulling a red wagon behind you when backpacking…so you can bring along more stuff you won’t use.
HUH?
The roots and rocks in the trail will be like the wind , waves and current. So if you backpack on a paved trail. or paddle on a quiet pond…then go for it, and enjoy. It sounds like an experience that I, personally, don’t need.