We are pretty "loose" with our vacation planning, although I've learned if there is someplace we really want to go, we need to plan ahead.
For the past 5 years we've spent a week or two at a cottage on the southern Maine coast, about a 5 min walk to the beach. However, the owner sold her properties to another company and the price has increased almost $1000 a week, so we are reconsidering. I'll miss it- it's a sunny, cheery place to be and my sister, brother, and their kids (all adults now) live in that town, and it puts me within an hour's drive of extended family, so it's a nice vacation, especially when we go for 2 weeks- good balance of family time, beach time, "us" time, but that'd be another $2K. Not sure we can swing it.
I (or DD and I) also go to Disney once a year, but they are very budget-based trips. Sometimes we don't even get park tickets, just go to stay onsite and soak it all in! However, we are planning a week-long trip in January '24 to take the resident 7-year old on his first Disney trip. This will NOT be a budget-friendly trip, but it's also not an "over the top" trip. All airfare is on points, we have rented a 4 bedroom pool home for $230 a night, we have about $1200 in ticket money on account with Disney (from trips canceled due to covid). We always do breakfast "in the room" but this trip we'll be doing most dinners at the house, too. OH and I have about $1100 in Disney Visa rewards to offset other ticket costs. Only thing I'm struggling with, budget wise, is renting a large SUV or minivan.
I guess I should also mention that i JUST booked a solo trip for me, 4 nights in November. Staying at ASMu, with a 2 day PH. I've been to Disney enough that I know what rides I want to do (nothing that goes around in circles or has big drops) so half-days in a park is usually enough. I'll do a park day, have a break day, do a park day. I'll probably hop to Epcot for Food&Wine for dinner both nights. It's "been a year" here and I need some alone-time, so Disney, here I come!