How have you spent more money than you needed to on a trip?

Extra leg space in aeroplanes.
In the ‘old’ days sometimes people with ‘normal’ seats could occupy an extra-space seat, when they weren’t sold.
Nowadays not.
If they are empty when the doors close, they stay empty.
I always book one of those seats.
6’5”

I find that doing a lot of research before the trip helps tremendously. For example: are there washing machines available at the hotel, for guests to use? If so, bring some detergent pods and you can travel lighter and do a load or two while you’re staying in the hotel. You can also buy detergent in a store when you are at the location, but if you have it in advance, you are likely to have paid less for it (rather than buying it in a tourist trap store which charges higher prices). That’s just one example.

As far as spending, I tend to be fairly frugal and consider anything I spend on as far as meals or tickets to be part of the cost of the trip. Sometimes I may buy a package (for example, there’s something called “City Pass” which is available for many cities in the US, and it is comprised of tickets/admission for five or six things). Even if I don’t use everything in the package, still, if I use ⅔ of it, it still comes out to be cheaper than if I paid individually for the different things I did use.

That’s pretty much the definition for every trip, and the virus was required to get my attention. The money we did NOT spend due to the lockdown is a shocking surprise.

Worse. Visiting my sister overseas. Hotel was supposed to be included in the travel package. It wasn’t. Big buck surprise.

I usually research before and avoid spending too much for something, but I’m sure there have been times I could have saved and didn’t.

I actually have had more regrets not spending to be comfortable. As I get older I spend more money up front rather than hope I’ll get a free upgrade or luck out. Even when I was Titanium level Marriott frequent traveler with a strong likelihood of being upgraded I often paid for a suite at hotels like Residence Inn if I was traveling with my husband.

I leave things to luck for short flights or one night stays.

I paid for tickets on line for a modern looking train ride that went from Budapest, Hungary to Bucharest, Rumania. When I got to the Budapest train station I was told I had to pay again and when the train arrived it was an old relic and a piece of shit. No air conditioning and the toilets employed onto the tracks. I should have taken a plane flight (cheaper and a lot faster).

^^I would love to see those same destinations. Thanks.