I'm not sure if you're serious but are you telling your family about this choice? Family always comes first and if you usually go on a vacation during winter you will probably get a lot of shit for spending the money on gear instead. However, if You got some extra cash on hand and plan on surprising the family with a vacation I would get some gear and buy some nice gifts for the family instead.
If my kids want a dream vacation they have to earn it by educating me on what tone wood would be best for my dream guitar.
I'm just kidding you please know that....in all seriousness I am buying the guitar or amp. Life is disappointing and there is no reason for me to spend good money to convince my children otherwise by teasing them with a week spent somewhere they won't spend the rest of their miserable lives.... and the concept of a family vacation together died with the cellphone in every kid's hand.
And there is a new EVH striped and a 2023 Hanneman coming out. You're question couldn't have come at a worse time for me financially
I bought my dream guitars before he was born. Like when we were planning for the pregnancy, I was also drawing up my custom shop order(s). A little foresight serves the gear buying well. Just budget for the vacation AND the gear if possible.
But always choose the kids first. They grow up so fast.
I actually did get a new dirt bike out of our honeymoon. She wanted to go riding for our honeymoon, and there was no way I was doing that without a brand spankin’ new fuel injected digital tuner compatible 250 cc four stroke.
OP, why wouldn't you want a vacation? Gear is awesome, but experiences are great, too.
Anyway, the choice is kind of a false dilemma in terms of practicality, like you've got Sweetwater and Expedia open in separate windows with credit card in-hand while there's a gun to your head. Of course, family/household is a priority, but you can always budget separately for discretionary purchases. Put a few bucks in the vejichan guitar fund once in a while; put a few more bucks in the family activity fund, too.
Besides, it's not even that much of a price gouger to get the dream guitar. Thus, making it a win-win for both yourself and the family. Anything else is simply not worth the time, and definitely not worth the money.
IMO if you're in a position where you have to make a definitive choice between the two, you might want to reconsider doing either of them. "I will be broke and have no other expendable money after this" would be a deal breaker for me in both of those choices, so I would either:
a) do neither until you can do both
b) compromise on both so you can do at least some version of both
c) do the family thing, so that the kids grow up well adjusted, get good jobs, eventually buy you the gear, and then you still end up at A in a roundabout way.
But before all of that -
Are we talking about "I have some spare money and I haven't decided what I want to do with it", or is there an explicitly expressed family plan - something they said they wanted, or you've talked about doing - that you're denying them so you can buy stuff? Those are very different situations.