I'd like a model of the benefits that holidays (vacations) can have, so that I can plan accordingly. Relevant questions that I have, although feel free to answer ones not listed here:

  • Do holidays teach you things about other places that you couldn't learn from Wikipedia?
  • Why are holidays more relaxing than just lying in bed at home and paying somebody else to take care of you?
  • Does visiting family count as a holiday in the relevant sense?
  • Are the benefits of tourism and/or pilgrimage the same as the benefits of holidays? What are they?
  • How much money should I be willing to spend on holidays?
  • Is 'holiday' a coherent enough category that I can treat it as primitive for the purpose of this question?
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I'm going to use the word "vacation," because it isn't overloaded with the meaning of "holy day," and you seem not to be asking about the latter.

Civilized working people spend a lot of time doing routine tasks, and don't do a lot of learning or encountering new things or places, relative to the ancestral environment. We also tend to stay indoors or otherwise in environments unlike the ones we evolved to enjoy.

People often feel better when they leave their usual place, and go somewhere they can experience either a lot of novelty (being in a new place and seeing lots of new things and people) or a place that would have been especially advantageous (and therefore pleasant) in the ancestral environment (e.g. mountains, hills overlooking rivers, seashores). Since most people cannot afford to run a household while doing this, they do it at short stretches. This is called a vacation (or "going on holiday").

Visiting family is another thing people tend to do in short intense bursts like that, as we tend to live much farther from family than we would have been in premodern societies.

Going somewhere to see or do a specific thing that's of affirmative interest (e.g. pilgrimage) can be very different, though it's often a pretext for a vacation (e.g. Canterbury Tales).

I think compared to other forms of fun, the novelty of vacations makes it easier to form memories of fun times (which can be revisited / discussed later at will), and that's probably the main reason to have vacations.

How much money should I be willing to spend on holidays?

You can start with local/cheap vacations and increase your range/budget as the local novelty is used up.

  • Benefits of vacations: they’re fun!
  • Drawbacks of vacations: sometimes they’re not fun.
  • How much money should you be willing to spend on vacations: as much as fun is worth to you.

What's fun about vacations though? Is it just that other places have more fun things than the place I live has and/or I'm now used to my local fun things?

How much money should you be willing to spend on vacations: as much as fun is worth to you.

This might be an even more naive question than those in my post, but how does/should one figure out how much fun is worth to them? In practice I just sort of use my gut intuitions, but I go on holidays rarely enough, and they involve large enough sums of money, that I don't have reliable gut intuitions. Do you just develop those intuitions by spending money on a TV and a holiday and see which one you like more?

Is it the case that you basically have not taken any vacations? If so, then I think a better question to ask is "what are some suggestions on how I might rapidly learn which sort of vacations are valuable to me and for which reasons, on a limited budget", since it's going to be pretty idiosyncratic.

My experience with holidays/vacations is that they're not worth it. However, I exclude a lot of things from the category of vacation that others might include. I exclude:

  • going to visit family
  • going away to a conference
  • going on meditation retreat
  • generally visiting someplace to do something

All of these are activities that can be fun and may count as "vacations" in the sense of "I took vacation days from my job to go do them", but they aren't really about relaxing or getting away.This may be due to my personality preferences, but I find the only thing I really think of as a vacation is having a long (at least 3 days, and the vacation only really starts on the 3rd day) period of unstructured time with no responsibilities. The more external pressure that gets applied to me, be it from the need to visit family, the need to keep to a schedule, the need to not lose out on money already spent on tickets to do something, the less it feels like a vacation.My ideal vacation is probably something like going to an all-inclusive resort for 1-2 weeks.If you have a sufficiently similar personality (I can guess at what factors affect it, but my overall personality dimensions are high openness, medium-high conscientiousness, medium-high agreeableness, very low neuroticism, and medium extraversion), you may find like me that there is a very small set of things that will count to you as a vacation worth taking; everything else will just be things you may value doing for other reasons but not for what I see as the purpose of a vacation—experiencing true, deep freedom.

One thing that I typically get out of holidays is having experiences associated with my interests that I would otherwise not be able to have. For example: musicals on Broadway typically have more talented casts than musicals elsewhere in the United States; looking at artwork in person is generally more emotionally moving for me than looking at it online; I met some famous people, watched interesting panels, and went shopping at WorldCon; and Disneyland has rides and the opportunity to interact with costumed characters.

I assume if you had interests such that going on vacation would benefit you in this way it would have made your list of benefits of vacations. But that is definitely one thing some people get out of vacations that might not generalize to you.

Another advantage of vacations for me is that many of my closest friends live very far away, and if I'd like to see them in person either they have to visit me or I have to visit them.

This is highly individual. I never go somewhere to "learn". (I completely agree that you can read the Wikipedia, and most of the time I don't even care.) Some people seem to have different preferences, hence the profession of a tour guide.

From the perspective of feelings, being somewhere provides you the full 3D experience, which is stronger than just seeing a picture on the screen. Even watching things in a museum or a gallery feels different than looking at pictures on the screen.

Some places provide you things you don't have at home: a sea, a mountain, a forest, a jungle... My typical vacation is going somewhere close to nature.

Sometimes you want to experience a different culture. Could be any kind of difference, just to have a novel experience; or could be a specific culture that you enjoy. People have emotional associations with some cultures, based on stereotypes, books, and movies: romance, adventure... You may want to practice a language.

Traveling somewhere means that you don't sleep at home. If you stay at a hotel, you have to pay for the bed and food, but you don't have to do the dishes and other annoying work; it is expensive, but pleasant. (Yeah, you could also rent a hotel room right next to your house, but this way you combine the necessity of living somewhere on a vacation with the luxury of having more service.)

And then there are the thousand different details, many of them unpredictable, that you can find in a different place. You may find a nice park, a nice cafeteria, or perhaps just a nice view, at the new place. Around your house, you probably already know most of these things.

Sometimes you go to a specific place to meet people who live there. Sometimes you coordinate with people who live far from you, to spend the vacation together at the same place.

...I probably forgot a few things here, but the idea is that a vacation is many kinds of things. Different people put different weight on individual components, thus you get different kinds of vacations (hotel vs camp, distant country vs nearby place, etc.).

Does visiting family count as a holiday in the relevant sense?

Depends. It will be closer to the "archetypal vacation" if they live far away from you, in a different kind of place (e.g. big town vs village), if their neighborhood is interesting, etc. But there is no official definition, and in real life it probably depends on how your partner feels about it.

How much money should I be willing to spend on holidays?

Depends on your income and spending habits. And what type of experience you aim for. Foreign travel will be expensive; local train can be cheap. Hotel will be expensive; you can also find a cheap accommodation. Some countries or regions are expensive, some are cheap.

My algorithm is something like: First, choose the type of experience, e.g. "somewhere near a forest, where I can take walks in multiple directions; also not one of the places I was at recently". Then choose the minimum level of comfort you can live with, e.g. "no cooking, a comfortable bed and a warm shower". Then look for the options, prioritizing for seeming interesting and being cheaper.

Is 'holiday' a coherent enough category that I can treat it as primitive for the purpose of this question?

Yeah, I think so. "Going to a different place, with the intention to have pleasant and/or novel experience." But of course some examples are more central (a hotel at the beach; a hike in the mountains; a guided tour in a foreign country).

Seems to me that "not being at home" itself makes a large part of the definition, although people can also go on business trips. (And you can make an edge case, such as a business trip in an exotic country, where the work is mostly a pretext to be there.)

feel free to answer ones not listed here

Try different things, find out what makes you happy. If you want to go with other people, different kinds of vacation may require different people.

You missed conversational and social signalling value. Travel is an excellent conversation topic as almost everyone has some memories that they'd love to share. Or at least I find it more interesting than most other smalltalk topics as you're at least learning about other parts of the world. And people who have travelled a lot are seen as more adventurous.

I deliberately excluded signalling value, since usually signalling activities have a pretext of usefulness, or are founded on that pretext, and I'd like to understand it more.

Almost everyone has some [travel] memories that they'd love to share.

Why do they want to share travel memories more than other memories?

And people who have travelled a lot are seen as more adventurous.

Adventure does seem like a function of travel that's hard to otherwise satisfy.

  • Why are holidays more relaxing than just lying in bed at home and paying somebody else to take care of you?

They're really not. If we just wanted to relax, we would continue our daily routines with fewer obligations. Holidays are about seeing new things, often accompanied by earned relaxation. E.g. it might be relaxing to lay around on the beach, but it'll be more satisfying if you've first gone to some effort to get there, explore, learn things.

  • Does visiting family count as a holiday in the relevant sense?

I wouldn't count a family visit as a vacation as it doesn't (typically) mean visiting a new place. Whether it's relaxing would depend on your family.

  • How much money should I be willing to spend on holidays?

Start with something very cheap and see whether you like it.

In general, people on vacation tend to pursue the same activities that people not on vacation do. So, if you like eating in restaurants, drinking, talking to strangers, going to museums, hiking, biking, reading, walking around cities, going to concerts, or spending time with friends in your normal free time, you'll probably like doing the same things on vacation.

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There are some types of learnings that require experiences to impart them. In that sense sometimes a holiday is effective at causing this to happen. It would be remarkably hard to cause some of those learnings otherwise.

What types of learnings? Why are holidays effective at causing them to happen? What should I do on holidays to get more of them?

Since it seems relevant to know where I'm coming from: I've been on holidays before, but almost always with my family, which I assume isn't as good as going on a holiday that you largely control the itinerary of with company that you choose. Sometimes, I get the impression that holidays/travel/tourism can have benefits that aren't obvious to me, like learning new things about different cultures or relaxing. If this is true, then trying out going on holidays without aiming for these benefits might be misleading about how good holidays can be.

I think most of this discussion is sidestepping a very simple, very obvious point:

Do you want to go on vacations to travel to various places?

If you want to, then do. If you don’t want to, then… don’t. What’s the problem, exactly? No one’s forcing you to go anywhere. Some people enjoy these sorts of things; other people do not. And that’s fine! It’s totally fine. People like different things. (And for different reasons, too! None of your questions have single, canonical answers—because people are different, and enjoy different things, for different reasons.)

I think you've summarized the question we're trying to answer pretty well. Does Daniel want to go on vacations? We don't know. How would one go about deciding whether they want to go on vacations? You seem to be missing the fact that one might be unsure about their preferences.

I assume that Daniel doesn't currently travel, is thinking about it but it seems expensive and is trying to build up a model of whether he'd get anything out of it.

I think that it’s best not to assume; questions like this are fairly pointless unless we know what OP’s reason for asking is.

And if he currently doesn’t travel, he should try it! Travel somewhere not too distant or expensive, see how it is.

And if he can’t afford to do even this, then what’s the point of asking the question? What does he plan to do with this information?

(Maybe these questions have good answers! But we don’t know what they are. So this whole discussion is unlikely to be productive…)

I thought my response to this mostly deserved its own thread here. Regarding the financial aspect, I can afford to travel, but it impacts my finances enough that I want to be careful to make good travel decisions, whatever that means.