Can I bring my cruiser board with me on a plane plus my carry on?

I am flying Alaska Airlines for 2 hours, Delta for 10 hours, and ANA (All Nippon Airways) for 2 hours on the way there and flying JAL (Japan Airlines) for 2 hours, Delta again for 9 hours, and Alaska Airlines again for 2 hours on the way back.

I travel really often to visit family and in the area where I visit everybody walks and the streets are not very crowded. This year I learned how to ride the penny nickel board mainly for the purpose of riding it around and I saved up money so I could afford it. Only after purchasing it and learning how to ride it did I realize I might have trouble about taking it with me on the plane. I am already bringing a standard size carry-on but I know I am allowed to bring a personal item so I was going to bring a tote so I could easily access things like laptop, headphones, blanket, and so on. I was thinking to maybe put the board in the tote but it would stick out a bit.. I am pretty sure my tote with the board in it would both easily fit under the seat in front of me. My board is the penny "nickel" board which is 27" long and 7.5" wide. I would have gotten the original 22" penny but it have been to difficult for a beginner.

The totes I am thinking about getting are http://www.aeropostale.com/product/index.jsp?produ... or http://www.tillys.com/tillys/variants.aspx?prod=21...