Originally Posted by Flying_Spaghetti_Monster
...I then discovered that although that I cleared it with them on many different occasions I still was not getting on the plane with my boat. ...
I used to call ahead, as recently as a year or 2 ago, but I no longer make it a point to call ahead. The oversized baggage policy for every airline is now so complex that the chances of getting someone who has the whole thing in their head is small. Just know the policy down to the smallest detail (even the plane size limitations are buried in there) and know your route to the smallest detail so you can say, no the oversized baggage embargo period doesn't start until May 30 or no, this is a 737 and they take this stuff.
More surfers are now stashing boards in their favorite locations and/or buying or renting locally (I left 3 boards with a friend in CR last time I was there). Surfers have always stashed boards around the world but it is more prevalent now. Kayakers should consider doing the same.
Leave a boat with a guide and tell them they can rent it out if they hold it for you. If you come back and they don't have the boat then kill them. If you aren't coming back then sell it before you leave (or buy one there). Quality oversized gear, like boats and surfboards are getting easier to find in remote locations because it is too expensive to bring them home.