Still, you guys assume this would be within the US, only. Excuse me for saying that, but that's some typical, US-centric kind of thinking. There's really whole world out there. If you're going to go for 2 weeks, go to Asia, South America or Central/South Europe and pay a third of the costs. Heck, do you know how cheap country side airbnbs in Portugal or Italy are? THAT'S how you build lasting memories.

Time becomes expensive then too… Jet lag is also a substantial issue. You have to accommodate the lowest common denominator in these situations. (People who have substantial family, don’t do well with jet lag, and aren’t very fond of long flights in economy)

Personally, 2 weeks is the minimum in my book for any kind of substantial time difference (4+ hours) and substantial flight time (8+ hours each way). I’m sure others feel even more aggressively than I do. I cannot imagine how people with kids would feel. The food and bacteria issues also just make things really challenging for many people.

There’s also the issue that you’re usually there for work, not just fun. Thus, you don’t really get to enjoy the spectacles as much because you’re gonna be doing 40+ hours working. I’ve been in exotic destinations before and had work stuff come up. It is not fun anymore. Terrible if anything. Rather be home than be in amazing place but unable to enjoy it.

You make some good points. Time difference is definitely a factor, but the thing is that with people WFH, you presumable are already dealing with people working in different timezones. So you organize those trips to always be somewhat within +-4h of the most of your employees. And those who can't join, will join into another destination. It would surely be one of those things you'd have to have a team dedicated to organize. But that's a team that would replace a bunch of existing, office-specific operational positions.

Food and bacteria – well, that's true. Although not everyone is affected and these come mostly from poor hygiene of either cooks/staff or the employees themselves. You make sure you choose a trusted and tested locations and educate your employees over tap water usage. I guess not much more can be done.

> There’s also the issue that you’re usually there for work, not just fun.

I think it's a matter of the vision. I absolutely would have made it to be more fun than work. First of all, in my example those would be frequent, so there would be less or no FOMO and not everyone would go to each of them. Which means you could definitely delegate the line support to those absent. If you ended up getting called in for help after all, that's just life. But, that's also unlikely to happen each time you getaway.

> you’re gonna be doing 40+ hours working

Well, no. I understand it may have been like this in your case, but it shouldn't be. I see those getaways more as a concentrated leisure/team-building activities you otherwise do throughout the year in the office and still get paid for. Except here you have an added benefit of actually being able to hold some really cool, out of the "cubicle-box" brainstormings/hackatons. Plus all the team building games, parties, etc. – again, all those things you'd normally do in the office to actually bond with people.