How do you afford multiple trips?

We have a good upper middle class income. We live in a not super expensive home. We actually live in a farmhouse flip we just completed and will be selling. We are going to build a barndomium to 1. Meet our personal needs better and 2. We’ll have a huge down payment from the sale of this house, and be able to pay off the Barndo fairly quickly.
I am starting to get into the cc game, as much as I’ve scoffed at it for years. By next month I’ll have enough points to fly all 5 of us on next years trip.
I rented DVC points for that trip. But I’d I don’t buy a resale contract by then, then the bonus I get in January will go toward buying one.

we have taken some really, REALLY low budget trips in the past. I don’t want to say we don’t have to anymore, bc I still am budget/value conscious. But.... flat out we just have higher income now and less, almost no debt (outside of house and car payments). My car will be paid off next month and I plan to drive it for awhile and enjoy that. I don’t really “save” for our yearly trip, but I do book it pretty far in advance typically. And then once I get about 5 months out or so, I start making big payments on it.
we have a lot going on the last half of this year, so I have a different strategy for the rest of the year. But my ultimate goal is to have a decent dvc contract of my own, and my husband and I to have AP’s once they return. I think being able to justkind of get ahead with those couple things, will make a huge difference.

also I will say- I’ve also been able to go to a conference in the fall, that is paid by work. I haven’t taken my family yet with me (a friend is coming this time) but plan to use that as our food & wine trip eventually.
 
We are a family of 8, and opting for one larger trip is definitely cheaper than two short trips. We went for a week last March and spent $12k and have a trip booked for two weeks in late September and it is about the same price even though it is double the days. We aren't DVC, but two rooms at POP is actually the cheapest part of the trip. Tickets are $5k and yes food for two weeks at the parks is very expensive, even when only doing one QS and some snacks each day. I miss the day when we could take a trip for $2,500 (lower prices and less kids).
And to kind of piggy back on this- I truly feel other destinations, are just as, or very near as, expensive as well. You’re just being nickel and dimed so it doesn’t seem like it. I can say in all
Honestly we have spent just as much trying to entertain ourselves in Myrtle Beach and Gatlinburg. And having to pay for each and every single little thing we do in those places, all day long, stresses me out and annoys me so much, it’s really not even worth going for me. By the time I get to Disney, it’s paid for and we can just do it, and not think well this ride costs us $75 for all 5 of us to do.... we end NOT doing all the things we want in other places bc of that.
 

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