Thanks for all of the thoughtful feedback! I'm going to answer a few specific things here and there without quoting because I am lazy
I keep a separate vacation savings account for my vacation expenses and I usually come back from a Disney vacation with about $500-600 in non-prepaid expenses but I have the money to cover it (and yes, I budget well enough during the year that if it was 2-3 times that it's not like I'll go without food or carry a balance for the rest of my life, I just don't LIKE that!)... usually I have enough left in my vacation account to cover some part of the next vacation.
Things I can't really prepay are the before flight park-sleep-fly hotel, food before and after (not at Disney), additional transportation costs like uber or rental car etc. I also use gift cards but always shoot $200-300 lower than I think I will use because there have been times I have not felt like eating in TS as much as I had booked and I do not want to be stuck with gift cards after (even though I know I will use them SOMEDAY) so I usually run out of gift cards 2nd to last day or something and start charging things to my card.
I think part of my worry about the cruise is exactly what people have identified - the "bucket list" feeling that you will never do this again. Chances are pretty good I really won't though. I took 5 cruises prior to 2005 with my ex husband and I think we pretty much overspent on all of them, but we were DINKs so it wasn't a big deal to pay the bill afterwards, it was just the sticker shock. That wast he days when cruises were much more reasonable, we did an Eastern Cruise and a Western cruise and then were "done" but then after 9/11 there were incredible deals, I think $799 for 2 in a cat 11 room for a 7 night the following january/february with a certificate for a $99 per person 3 night cruise the following fall so that was cruise 3 and 4 and then we did the return after the first panama canal cruise in 2005. That was the last time I sailed until 2018.
Since being a single mother to a special needs kid, money has been a lot tighter than those days. Someone asked if I budget the rest of the year why don't I really want to on vacation and the answer to that is for a week I like to spend like I want to and not worry about it. It took me a long time to be able to afford to take my son on vacation and I took some extra time to save up enough to vacation the way I like to. I own DVC from back in the day so that helps but I wanted to do all of the TS I wanted to do, the character meals he wanted to do, extras like dessert parties etc... and it was awesome to just be able to do it all (and not worry about the money). I work crazy hard most of the year so it's nice to reward myself with a week of "anything goes." I'm not a gambler and I don't care for bingo so I'm not going to spend money that way (I went to vegas and did $5 in the slots before being bored, lol). I like a nice cocktail or glass of wine but can't see myself racking up major bills in that (mostly because it bloats and inflames me and I gain too much weight!)
Taking the kiddo on a SWDAS cruise was a total bucket list item for me and I had it booked in 2018 but then my parents wanted to join us but do a shorter cruise so we ended up doing a 4 night Dream instead with them and I rebooked onboard hoping I'd be able to swing the expensive cruise 2 years later and that goal is well within reach now. But I don't really anticipate being a frequent
DCL cruiser in spite of the number of cruises I've taken, it is just too expensive for me to do on a regular basis.
I just don't want to be worrying about it on vacation. I keep a few layers of savings - I keep a vacation savings account, in addition to a large surplus in my regular checking account and my regular savings so it's not like I imagine running up some kind of a tab that I won't be able to pay for, I just don't WANT to have much if anything that is not completely prepaid. It's not about restraint in spending, it's about planning for it (though I do restrain the kid as a lesson).
I am about 60% paid off on my cruise since my end of January trip to WDW and after my next work bonus in the next month, I will be 80% paid off for a PIF date of end of October, so I'm in fine shape for paying for things. I have $400 in southwest gift cards for the flights so I can probably hit whatever savings goal for onboard expenses I set without too much worry. I just want to get pretty close and not worry about it while onboard like I do with my WDW trips, where my handle on the budget is much better. I'm sure there will be a few extra merchandise purchases with the star wars stuff.
I do say "no" to my kid a lot throughout the year to the "I wants" so I like to treat him to extras on vacation like popcorn (which he has every night here, it's kind of a routine and the refillable buckets are a godsend!)... so if a refill is $2 I'm not going to make him eat french fries instead to save $15 over the course of the cruise. I'm just going to budget for the popcorn. We do go out to eat every so often here but I always make him drink water unless a beverage is included (it's often not because I live in a place with no chains... even chips are not included at the mexican restaurant)... on vacation I'd like to say "yes" to the smoothie if he wants it. So if I spend another $100 in smoothies and premium ice cream treats I'm fine with it. I just want to plan for it and not have it snowball to a horrifying total at the end of the trip
