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I am going to be in Madrid for a week or so next summer. Mostly work, but probably also some free time. I have been studying Spanish for a while now, and I got to the level when I am mostly understanding written text, at least up to the newspaper level (though some rarer words are missing, but mostly I get through), but when I listen to the radio it's about 50/50 chance I can understand. I know most people these - especially in tourist places and hotels and so on - would speak English likely, but I think it'd be cool if I could speak Spanish to them - and especially understand them speaking Spanish to me. Any suggestions about how could I increase the likelihood of this happening?
Relevant map.
I had the same experience as @charlesf whenever I was in Spain or talking to Latin Americans. Most people seemed happy to hear me attempt to have a basic conversation in Spanish and were very patient and helpful with vocabulary, except for Catalonians who however lit up with joy when I said a few words in Catalan and then promptly overestimated my ability to understand their language.
That's my problem too - I can squeeze out some basic Spanish phrases (donde esta la biblioteca?) but my capability of understanding the answers goes down quickly. Especially if the environment is noisy, as my hearing is also not what it used to be (it's mostly ok but I could miss some details and when trying to parse a language I am not well versed with, it starts showing).
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My experience has been that people in Spain react pretty well to being addressed in (competent) Spanish by visitors. In fact this has been my experience in every Spanish speaking country. Especially since English isn't anywhere near as common in Spain (and Italy) as Germany or the Nordics (I suspect France as well, but they'll never admit it). Depending on how you learned Spanish, you might want to brush up on some of the word useage and phrases common to European Spanish. I've found the Madrileños fairly easy to understand once you get used to the seseo. You can watch Spanish news broadcasts to get an idea. Other parts of Spain I've not done as well understanding them, mostly Andalucia, despite it being my favorite part. Most educated Andalucians can switch to Castillian without issue though.
I've only been to France a couple of times for work, and of course IT professionals all spoke very decent English, but from the people in service (waiters, ticket clerks, etc.) it was very much hit or miss. Some spoke absolutely zero English and basically refused any attempt to bridging the language gap. Once I had to use ticket machine instead of the ticket booth because the clerk refused to understand anything (which is kinda weird in a railway station - they must have significant tourist traffic there) and once I had to go to another restaurant because they didn't have any non-French menu and refused any attempt to discuss the order in English (it was before Google Translate time of course). It wasn't too bad in general, I found my way around to food and transport fine eventually, but I got the impression that some people in France definitely don't want anything to do with English. In Germany I had an opposite experience - we once got lost on a train station and asked some German ladies (in English) about it and they gave us super-detailed explanations and refused to part with us until making sure we made to our train, and their English wasn't that great (better than my German for sure!) but they were extremely enthusiastic about using it. We felt a bit uncomfortable that we took much more of their time than we planned to.
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Most people in Spain do not speak good English. The spread of English in Europe has been exaggerated (with a few exceptions). Yes you'll be partly understood in tourism heavy locales but you won't be having particularly satisfying conversations in English with the average Spanish person. A lot of subtleties will be lost.
Learning the local language is usually a better bet. Regular exposure is the key. I would try to find one or several practice partners for voice chatting. Watching Spanish movies with and without subtitles every week might help. Maybe voice AI could be of help too. I'd try to branch out from learning the written language. Actually speaking it yourself is important to get used to.
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