We have many years of sea kayaking on Lake Superior (long, slim, fast, stiff, lightweight kevlar boats--even the doubles). We began fishing more often and tried a couple of Hobie PA's for their fishability--we were surprised we liked them as much as we did--(short, wide, flexible). We bought sails with them, just for fun. The sailing started to cut into our fishing time and we added a Tandem Island. Four years later we are no longer car-topping, but trailering with a 6x12 ft aluminum enclosed trailer.
To pull it: At home, we use a medium size suv; For trips we use a 24 ft class B RV. Yes, as you noted, the total length is 38 ft. We take up two pull-through spots in a big box/supermarket parking lot. More importantly, the trailer is light enough that we can detach it, and move it by hand, to fit tight camp or launch sites. The trailer floor is also aluminum, so rust isn't a problem when we fish salt water. Everything but the TI is enclosed, locked and out of the weather. FWIW, we did not have the trailer when we picked up the TI, but it fit inside the class B RV (disassembled)--not a routine approach, but we used it once.
Here is a pict of us packed ready for launch to a Florida fishing trip later this week.
Here is the inside with the two PA's
We have two options to load the TI; one we learned from a fusioneng post: If we have 2 people, I run a line from the TI bow to the front of the trailer carrier pipes, through a pulley and then back to the TI bow, where the 2nd person can control the bow with the line. Then I lift the TI's bow (hull only--the amas, etc are removed) and set it on the roller at the rear of the pipes--maybe am lifting 1/3 of the TI's weight. With one person pulling on the bow rope and the other pushing/lifting the stern the TI slides fine along the pipes.
Here is the front pulley where we thread a bow line
If only me to load the TI, then I hook a very long folding ladder to the pipes at the rear roof. The ladder has coroplast covering its rungs for easy TI sliding. I replace the pulley on the bow pipes with a winch and use a hand-held wired remote to pull the TI up the ladder ramp. With the winch, I leave on the amas/seats/drives. Without the winch, I only lift the bare hull.
Here is a bad pict of the winch--it fits over the two bow pipes--winch above, battery under it
Here is a pict of the inside showing the PVC pipes and wood rack holding the PA's
We considered a trailer long enough to enclose the TI, but decided to go with the shorter/lighter option. At home, we have a trailer for just the TI (a wood deck (covered with coreoplast) with PVC pipes, set on top of a small boat trailer), so we can launch fully rigged with the ama's extended. For the trips when we take 3 boats, we use the enclosed trailer option.
If a trailer is used, the tow vehicle can get smaller, as gear can go into the trailer. For example a 20 ft class B like the Winnebago Revel, (has 4x4 drive and more ground clearance), would shorten the total length to 34 ft and allow travel on uneven/unpaved routes.