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Would I be able to bring a backpack and my skateboard on as a carry on and personal item respectively, or would I have to check it in?
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You should be fine carrying both a backpack and a skateboard onto the plane. Here's Southwest's official policy regarding skateboards:
Skateboard, may be substituted for a carryon or a checked bag. If the skateboard fits under the seat, it does not need to be in a bag or covered, but it does have to be stowed with the wheels up so that it doesn't roll. If stowed in an overhead bin, a skateboard must be stowed with the wheels up and needs to be in a bag or have the wheels covered (trash bag is acceptable) so as not to damage other articles.
Many people carry on much more/bigger items so I don't foresee any problems for you. You should probably bag it as mentioned.
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anyone know if there's a length limit for this? i have a longboard that is about 4 feet long
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I don't have a specific answer for you -- just my personal opinion.
Since the max dimension of a carry on is 24x16x10, I suspect that something that is 48+ inches long might be stretching it a bit. You might get away with a 30 inch board.
If someone has anything more authoritative than my opinion, please speak up.
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I’ve got a 38 inch longboard myself, and was wondering if I’d be able to take that plus a carry on bag. About a year ago I had seen someone with a similar sized board with them and just wanted to make sure it’d be alright taking that size myself before I get all the way to the checking station and get told I can’t take it.
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@tmeyerrose wrote:I’ve got a 38 inch longboard myself, and was wondering if I’d be able to take that plus a carry on bag. About a year ago I had seen someone with a similar sized board with them and just wanted to make sure it’d be alright taking that size myself before I get all the way to the checking station and get told I can’t take it.
The board is too big to fit under a seat, so it would not qualify as a person item. Southwest says it can be a carry on, but you are limited to one carry on and not two. The question becomes can your carry on fit under a seat? If so, it's a personal item..
"
- Skateboard, may be substituted for a carryon or a checked bag. If the skateboard fits under the seat, it does not need to be in a bag or covered, but it does have to be stowed with the wheels up so that it doesn't roll. If stowed in an overhead bin, a skateboard must be stowed with the wheels up and needs to be in a bag or have the wheels covered (trash bag is acceptable) so as not to damage other articles.
https://www.southwest.com/html/customer-service/baggage/special-luggage-pol.html
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Well the bag itself is small enough to fit under the seat. But if I am unable to fit it then I’m not going to worry about the longboard then