We've talked a lot about vacations over the years — how to prepare your workload for a vacation, how many days you get to take vacation, whether you repeat vacations, how to travel solo, etc., — but we haven't really talked about how you pay for your vacations. Readers were discussing this a bit recently, so let's get into it!

How do you pay for your vacations, readers? With your bonus or other “found” money, by saving money either in the abstract or belt-tightening in the months leading up to the vacation, by putting it on credit card and paying it off as you can, or some combination thereof? Do you save for the big things like flights and hotels and then give yourself a daily budget while traveling? Where do you think vacation spending (or vacation saving) falls with your other spending and saving?

(If you're coupled, how did your vacation goals change once you got married or partnered? For those of you with children — how have your vacation goals changed as they've grown?)

How I Pay for Vacations

As I've mentioned before, my family and I heavily use automatic savings to save for these kinds of goals — we figure out roughly how much we want to spend on vacations, then divide by 12, and save that amount monthly.

Other friends set aside a big chunk of their bonuses in order to pay for relatively lavish vacations, and I definitely know friends who have chosen to focus on other financial goals and thus don't travel a lot.

I didn't travel a ton in my 20s because I didn't feel that comfortable traveling by myself, and coordinating with friends seemed overly complicated at the time. To be honest, I just kind of assumed there'd be time to travel with my future husband — but other things took priority once I found my guy, such as buying a home and having kids. And since then a lot of the travel budget has gone towards visiting family members so they can spend time with the kids.

Readers, how about you — how do you pay for vacations?

Stock photo via Stencil.

{related: not sure what to do first/next in your personal finance journey? here's our money roadmap}

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Readers, how have your vacation strategies changed over the past few years? Are there places you won't go now (or times you won't go there) that you might have gone in years prior? How much are extreme weather/climate change, politics, pandemic response and restrictions, transportation problems, and other issues affecting your decisions? Are you trying to plan as many vacations as possible right now because you've maybe missed, skipped, or limited vacations since 2020?

For my $.02, I am trying to be more aggressive about planning vacations for the family, but a lot of the above factors are affecting our decisions. My husband strongly prefers direct flights, and with the airline woes that seems wise. The pandemic restrictions have limited our hopes of international travel until recently (I've had too many friends stuck in Switzerland or places because they tested positive before they returned), and I think it'll be years before we feel comfortable taking a cruise (but then it's not like we were cruise people to begin with — we've never taken one). Even now for kiddie vacations we strongly prefer outdoor waterparks to indoor-only ones.

Do tell, readers – how are all of these things affecting your vacation decisions?

Stock photo via Stencil.

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It's been a while since we talked about actually taking vacations, but with Memorial Day almost upon us (yay!) and lots of people gearing up for big summer vacations, let's discuss. Readers, what do you do at work to prep for your vacation? Do you think there are different things to do to prep for your vacation if you're fully in-office, hybrid, or remote?

(Another question: Are there any positions or workplace dynamics in which you really just feel comfortable checking out completely for a week or more without significant prep — and what do you think those are? More senior, more junior, not customer-service oriented, etc…)

{related: we asked the readers: how many paid vacation days do you get every year?}

Things to Do at Work to Prep For Your Vacation

Some suggestions:

Plan, plan, plan. Know what's due before you leave, when you're gone, and when you return. Prioritize things based on the schedule, but also based on how much work you can get done, if needed, while on the plane or (heaven forbid) the vacation itself. For example: that fact-based project with a zillion binders, moving pieces, or many people involved in the decision chain? Get that one done at the office. That article you're writing — for which the research is done but the article is heavily in need of editing? — that's a great project for the plane, if it comes to that.

Let other people know that your planned vacation time is coming soon. This depends a lot on the dynamics of the office — I've done everything from emailing my superiors (and subordinates) to let them know it was coming up a week or two ahead of time, to leaving a travel guidebook on my office desk (as a silent reminder).

Leave your office well-prepared. If you're working on three or four different projects, leave a pile for each on your desk so that if a question comes up in your absence, your coworkers have at least a fighting chance of finding the answer themselves. Also, I've always left a printed sheet with my itinerary, my hotel information, my cell number (and my traveling companions' numbers), and anything else pertinent. You may want to even “schedule” a time each vacation day to answer emails and voicemails, so other people know when they can expect a response. (Obviously this depends on your seniority and on how many fires are going on at the office when you leave.)

{related: what to know about taking vacations alone}

Some more suggestions from the commenters on previous discussions about this:

• My coworkers and I try to make each others’ vacations a little easier by divvying up each other’s work while we’re out. So, if I were going on vacation next week, I would meet with my two coworkers and split my ongoing projects between them. For each project, they get the latest drafts (or instructions if there is no draft), the client contacts, and I tell the client to contact Coworker Jane with any questions or issues about their matter while I’m gone. When Coworker Jane takes her vacation, I reciprocate. Coworker Jane and I trade cell phone numbers for emergencies, but we rarely use them. This works so well for us that we can generally take an entire week-long vacation w/o a single call from the office. If you can work out this kind of shared-work arrangement with your colleagues, it’s a great way to make sure you don’t have to kill yourself trying to clear the desk entirely but can still really unplug when you take your vacation.
• I build an extra day when I return. We fly back in on Saturday so we can adjust to jet lag and do laundry, catch up on email, triage the inbox. If things got so bad on getting things in order before I left, I would consider building an extra day on the start of vacation, plan to take Friday off to adjust people to my time off. Finish things up at home to help transition out. But really, something always happens. People can survive without you. They don’t want to, but they can.
• I usually try to draft a quick note on each case/issue that might possibly come up and email them to anyone who might get involved. For example “The Smith case involves (subject), and nothing’s due until X, but client may call about Y.” Just so they’re not entirely lost if something does come up.

{related: do you repeat vacations, or try new vacation destinations?}

One lawyer had some great tips:

I’m a lawyer, so different but still similar issues with vacation – unpredictable deadlines, focus on client service, demanding bosses and colleagues.

I leave a detailed list of every matter that I’m working on if I’ll be out of the office for a week or more. I give it to my assistant, and it includes a short description of the matter, the status (i.e., letters have been sent, waiting for response), the external contacts who may call about the matter, and the internal contact person who can handle it while I’m away. I find it to be a helpful way of making sure I’m not missing anything, and helpful when I return so I can just pick up where I left off. My assistant likes it because she has something to say when a client calls (“Mrs. Emcsquared is out of town, but Mrs. Jones is aware of this matter – may I forward the call to her?”)

And I like to set aside a half hour each vacation day to clear out my e-mail. I don’t generally respond outside the firm; I just forward to my internal contact and let them respond. I hate coming back to a full e-mail box. Finally, try not to send any e-mail for 3-5 business hours before you leave town (meaning, if you leave at 6 am, don’t send e-mail after 3 pm the day before). The more e-mail you send, the more you get back…and if you do have to send an e-mail in that window, make sure it’s a complete and organized description of your conclusions and proposals, not just a “let’s talk about this” e-mail.

And while you’re on vacation – put your phone in the safe and turn off the ringer. Or switch off the e-mail synch function, or disable the e-mail notifications. I did this accidentally once, and have done it intentionally ever since. Truly worthwhile.

Readers, what things do you do at work to prep for your vacation?

These are some of the Corporette readers' favorite items for business travel…

Stock photo via Stencil.

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I don’t think we’ve had this conversation in a few years, so let’s discuss: What “vacation time” comes with your job? What happens if you don’t take the time? How much time have you taken off in recent years, as a percentage of what you're eligible for? (If your company allows remote work, do remote workers have the same vacation time packages/expectations as in-office workers?)

I’ve seen four main kinds of paid vacation days given by companies:

Earn your vacation time: You have to work to earn your vacation time. At a smaller office, a newer hire may be prohibited from taking extensive vacations, especially around holidays, as more senior members get first pick of when they’ll take time off. Sick days may “blend” a bit with vacation. (I just saw someone tweeting about how she had worked a zillion days straight while trying to “save up” for her maternity leave. Whee!)

Use it or lose it: Your company may give you a set number of days for vacation — and if you don’t use it you’ll lose it. In my experience, people with these packages are the ones who take vacations the most, even if they’re just restful staycations, because it’s part of the company culture that everyone takes that number of days off.

Rolling over vacation time: Some companies grant a set number of vacation days, and those vacation days can roll over from one year into the next if they go unused. This can be ideal in a situation like a pandemic, where travel can be difficult — but also if you want to bank your days, either for a big trip (honeymoon!) or to extend a limited maternity leave, especially with a small company where FMLA doesn't apply.

”Unlimited” vacation days: These benefits SEEM like they'll be amazing at first because, woohoo, unlimited vacation! But in my experience a lot of people in these jobs take less vacation than people with limited vacation days. I think this happens for a few reasons, the biggest of which comes to company culture — without the “use it or lose it” mentality, a lot of people just don’t take vacation. (On the flip side, I know one friend of a friend who's the top executive at a hospital who has taken probably 10 weeks of vacation between January 2021 and now … so if you can actually take it, good for you!) If you have unlimited vacation days, I'd love to hear how many you take, and what a “reasonable number of vacation days” is (unofficially) among your coworkers.

So let's discuss, readers: What do your vacation benefits look like? Does your office or team have rules (written or otherwise) on who can go on vacation at what time? Finally, how much vacation have you taken in recent years (and how much are you planning to take over the next 12 months or so)?

Stock photo via Stencil.

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We're talking about family vacations in 2022 over at CorporetteMoms, and so let's discuss here — even if Omicron is changing your holiday plans (as many are noting in this morning's open thread), are you still hopeful enough for the State of the World to plan travel in 2022? And if so, where are you going, and with whom? Are you planning solo travel? Destination friend weekends? International family meetups? Do tell…

(Also — where are your favorite resources for researching possible travel restrictions? Are you doing the “trip stacking” all the travel sites are talking about? What kind of travel insurance/cancellation insurance do you trust?)

For my $.02, nothing is planned yet, but I'm hoping that now that we're all vaccinated and boosted we can consider flying at least a bit… that said, one of the commenters on CorporetteMoms noted that her family cancelled a beach house vacation rental because they were concerned the local hospitals were overflowing, which is a consideration I hadn't really focused on previously — and it's enough of an “of the moment” concern it would make me worry about planning. Deep breaths…

Readers, over to you — what are you planning for 2022, and how are you researching travel restrictions and cancellation insurance?

(Stock photo of Kyoto via Unsplash / @blackodc.)

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Here's a fun question today: Where did you go for your honeymoon, Very Romantic Vacation, or the best vacation of your life? (Was your honeymoon the best vacation of your life thus far?) If you could take two to three weeks right now to go anywhere in a perfect world (free of COVID and conflict and climate change woes), where would you go?

I was updating an older post on wedding registries and this struck me as a good topic, and one I don't think we've discussed before. Where would you recommend people go for their honeymoon?

For my $.02, we were married in 2009. We went to Aruba for a week, in part because my wonderful FIL promised to pay for it, which was amazing, but I felt a bit more constrained in budget than if I'd have planned it myself — I might have sprung for a two-week trip somewhere farther flung like Bali or the Maldives. (Looking back, I wish I'd just asked him for a budget contribution or something that we could then build off of, but… ah well.)

Aruba was a lot of fun, and honestly just what we needed after the stress of the wedding and week prior. My “I'm going to plan the entire wedding myself with lots of small, thoughtful details” devolved into us imposing on close friends to complete projects, like the seating chart, the night before the wedding. (Thank you, Martin!) There was also some fun with the blog — I was still Very Anonymous, and the big NYT article that really put us on the map came out about a week before I got married. The reporter's email went to spam… my hosting site shut us down because of too much traffic… fun! My husband also got sick right before the wedding and lost his voice.

In any event, with all the stress of the wedding, there's no way we could have done a big sightseeing vacation with multiple stops or complicated travel — sitting on the beach with piña coladas was kind of just what the doctor ordered, you know? It was lovely, but more because of new husband + beach + cushy accommodations + finally being able to eat garbage after being, perhaps, overly strict with my diet before the wedding.

In terms of what my BEST vacation ever was, it's hard to say — my Sedona girls' trip is up there, so was the first time my husband and I went to Paris together. After being disinclined to travel for the past year or so, now I feel pressure to plan the Best Trip Ever.

So readers who've been on the Best Vacation Ever, please shower me with some ideas! In general, though, I'd love to hear where everyone went on their honeymoon, what it was like, and where you'd recommend other people go…

Stock photo (Maldives) via Stencil.

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