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We have done a lot of group kayaking with Hobies, mostly in the keys and around Key West. We used our TI as a kind of mothership, then tow several hobies and othe kayaks out to remote islands (usually 3-5 miles) for the day.
We mostly only go out in really flat water and very low winds. At first we were all hanging into the TI with everyone peddling and just hanging on to each others boats, wasn't very fast, we would make maybe 3mph. The stock main sail only on the TI was of little to no help in very light winds, basically peddle power. Makes for a really long day in 95deg heat and sun.
I would imagine a side by side rig (two TI's hooked together), would have similar performance to the above party barge ,( what we called peddling as a group).
Later on we had much better luck and could go much further and way faster using our sooped up TI (with massive sailsets, wing sails, and twin big ole outboards) as the mothership. We then towed a 4person inflatable, that we used to store scuba tanks, coolers,etc on about 15 ft directly behind the TI (on the centerline). If we had other kayaks they would tie onto the raft in a line, or just hang onto the side of the raft. We tried lots of times having the kayaks hang onto the TI, next to us, but that didn't work at all. We couldn't steer the TI at all with any other boats hanging on the sides of the lead boat.
One thing that really worked out well for us with our hardened TI, was to tow other TI's out to the remote islands, once there we would all separate and do our own thing. Our souped up TI easily cruised 10-12 mph in very light winds, (actual wind direction and speed made little difference in speed, (even almost directly upwind). What we discovered is if the towed TI sails about 45 degrees off our stern, about 30 ft away, ( in clean air, we used 3/8" anchor line to tow with). Both boats together could easily maintain around 10mph, ( in open ocean). Add a third TI to the string we could still maintain around 8mph steady. The following boats are using the apparent wind generated by the lead boat with their sails, so there is very little power loss. We would often go up to Cotrell key (about 7 miles), A stock TI might make 4mph in those conditions, ( with much tacking, (these boat don't point very well when stock)). When towing, once at the destination, everyone separates and does their own thing.
I'm not touting or recommending anything here, just sharing what has worked out well for us.
FE
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