Get out of winter and skate some place warm this January. While this WOULD be an amazing opportunity to bring your Skis / Snowboard along, TAP Portugal is insane with their Snow sports fee (100 euros each way). Carry your skateboard on to and avoid the hassle.
Boston to Barcelona is routinely $450+, this saves you better than 30%.
On the plus side TAP DOES give you one free bag and is considered a full service airline so letting this deal pass just because we can't bring the snow gear doesn't seem to make a lot of sense.
Particularly given the fact that Barcelona has got to be one of the top 10 skate (downhill or otherwise) destinations in the world.
Seeing is believing as far as the street features in Barcelona are concerned. Heres a few clips from GoPro to get the feeling right:
While this next one isn't IN Barcelona proper, it bears repeating, the whole city is on a hill. To make that even insane the Catalan government happens to be in favor of cheap public transportation from the bottom back to the top.
Here's Aleix Gallimo finding a little solitude a little further outside the Barca city limits.
While that specific road may not be open to skate, odds are 100% you can find some ridiculous hills that are.
Most of this stuff happens late fall and early winter but there is a reasonable amount of availability. Search around and you will find it. Oh yeah, avoid Norwegian if you don't want to pay bag fees.
As much as TAP sucks for charging for ski equipment, it sucks even more paying for your carry on (and everything else) with Norwegian.