Am I the only one that has a hard time spending money for vacations? I recently retired but even before that other than going to see family I have not took a vacation since 2002. Every time I add up the dollars just can't to it. Be easier if had someone to go with. I am ahead of my budget for the year and trying to talk myself into something. Actual trying to talk myself into Mexico. I have had my shots but looks like still need to be tested before return trip.
I have some trouble but mostly because it's not "my" vacation only hahaha.
I was also looking at Mexico but that test before return has me apprehensive.
I would suggest starting small with something like a baseball game at like Fenway Park, Wrigley Field, or somewhere else iconic for a weekend trip with a big event. Choose a different sport if baseball isn't your thing but you get the idea.
Another small but fun thing is to find a festival or some other activity you would like to attend for a weekend.
I've traveled a ton for work and also been able to do it for leisure and I can tell you that 95%+ people who "love to travel" don't do it in a way I would consider enjoyable but more for the reason of posting pictures online and being able to tell a story. I prefer to have an experience vs a story to tell.
So starting small is sticking with an event. Or choosing a relaxation destination where you can fish, relax on the beach or in the mountains etc. AlsoI highly recommend you plan no more than 1 event and 1 meal per day or else you end up spending your whole vacation running from event to event and managing a schedule.
Finally location, location, location. Don't EVER skimp on location. If you want to go to the beach STAY ON THE BEACH.
If you want to go watch a sporting event STAY WITHIN WALING DISTANCE of the event!!! Stay where you want to be.
Also don't shrug off local stay-cation stuff. You can do 10x more stuff ubering and staying locally than buying a plane ticket and staying in hotel rooms for nights on end :)
Try some stuff out and let us know what you think.