Lyman might fit the bill well as it was designed after the trip in mind. i have ridden both and thought the lyman was surprisingly loose despite its multiple fins.
as for the gator boards, not so sure what to say as i have not ridden them. the description on the caddy says, "Cupped, full-length center channels give this board more control" which makes me think it might be pretty grippy and not so "roamy" ???
as for "roamy," the (mostly) featureless bottoms of many of the flex boards make them the "roamiest" boards i know of and super fun to ride too. slingshot response, company recruit, humanoid oracle (when it comes out) or even the ROAM ;)
(Message edited by wakerider111 on February 16, 2009)