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Flew with a playboat on southwest a few years back, barely got that past the checkin counter, because there is also a max size criteria (length+width+height) to contend with. I have a number like 120" stuck in my head, by a quick googling looks more like their current general size limit is 80", which seems like it wouldn't allow a playboat anymore, let along something 150" long. Probably worth contacting them directly, and then getting approval (if possible) in writing before attempting the checkin process...
 

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Nah, dude. Just buy a used surf board case, tell Southwest it's a long board, and if you're lucky, they won't know the difference. It has worked before.
 

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I have yet to see any coherent rational in the part of the airlines on what they do about kayaks. On one trip to Ecuador with a bunch of folks, we were in 3 different lines and each boat in the different lines got on for different prices. I gone to the airport and talked to one person at the counter a couple of days before my flight and got one price and came back 3 days later checked in with the same person and got another price. It has been a guessing game every time I've flown with a boat. Good luck
 
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