Reposting a relevant answer that I wrote last year on Quora (http://qr.ae/I5tZ7 http://qr.ae/I5tZ7): I work at Factual, which has an unlimited vacation policy.

Reposting a relevant answer that I wrote last year on Quora (http://qr.ae/I5tZ7 http://qr.ae/I5tZ7): I work at Factual, which has an unlimited vacation policy. The amount of vacation that people take varies greatly. At the high end, I've taken about 8 weeks of vacation during each of the last two years. I tend to do some work during vacations, however, so it's more like 8 weeks abroad in which I happened to squeeze in 4 weeks of work at odd hours. I think a few of my coworkers also take 4-6 weeks per year. Most of these people are pretty disconnected when they travel. On the low end, some of my coworkers don't take vacations at all, or take one week per year and then feel guilty about it. I understand their guilt about as well as they understand my wanderlust =). Things that affect how much vacation people take: * How long you've been at the company. Someone who just joined is much less likely to take a vacation than someone who has been around for a few years. * Your place in the company hierarchy. More senior people seem more comfortable with taking vacation than more junior people. * Schedule pressure. If you're working on a huge project that will take 6 months, you probably won't try to take a vacation during that time. * Being the only person on a project vs. being one of many. If you're the only person who knows how something works, you tend to worry a lot about what can happen while you're gone. * Personal budgets and travel preferences. If you like hiking trips, 6 weeks of vacation won't set you back very much. If you like overwater bungalows in Tahiti and private cruises in the Galapagos, then you need to have a lot saved up to take more than a few weeks off every year. * How much you like to take vacations (or how much you love your work). Some people like work enough that they don't want to take vacations. Others don't really care for vacations, so they might take a personal day or two but not go on longer trips. * Your, ahem, cojones. Generally, if you ask your boss reasonably, you will get a "yes" 90% of the time. A lot of people are afraid to ask. When our unlimited vacation policy was established, it seemed like people were waiting for their peers to set the boundaries of what was appropriate and what was not. Over time, I've realized that people are just different. People who don't take breaks don't seem to change their habits even when they see others take frequent vacations. Conversely, people who take frequent vacations don't seem to tone things down in the presence of non-vacationers.