Story time:
Back in 2004 i went on a five day trip to NYC with my girlfriend at the time. I was really into her and didn’t bring my board so i wouldn’t be tempted to skate and ignore her.
While on the trip she asked me why i didn’t bring my skateboard, and i will die regretting i did not skate the banks and other NYC spots we came across during our explorations, when i was young and energetic. (Even if i skated it now, it would not be the fucking same.).
So, last month, going to SF for five days, almost did the exact same thing of not bringing my board so i wouldn’t ignore my wife.
But this time, to hell with that. I brought it and am so glad i did: skated that UN plaza and in the middle of the streets of SF (no bombing hills because fuck that, y’all psycho, haha. Mad respect) i couldn’t do much, and got tired really quickly… but i won’t be living with regret now that i did some skate tourism. (Looked at Pier 7, and was happy to see it, i didn’t have a chance to see Third and Army, but that’s okay… no time for everything)
So, yes, always bring your board and don’t live with regret. The worst that happens is that you just don’t use it. Better to have it though.