Strategies for Paying for Vacations

Kyle and I committed to attend the black tie wedding in Chicago that I’ve mentioned a few times.  In addition to attending the wedding itself, we are going to make it a long weekend to see some of our good friends who live there as well as sight-see as we have never been to Chicago before.  We are excited to make some amazing memories!


Financially, though, the trip is going to be a stretch.  We haven’t totally planned our itinerary yet but we’ve already spent $225 on the wedding gift and a tuxedo for Kyle.  We can cover our lowest estimate with the money in our Travel and Wedding Gifts savings account, but that will require bringing our lunches with us from Durham and maximizing our couch-surfing opportunities.  If we want to upgrade some aspects of the trip or can’t keep things quite as tight as we would like, we might have to find some other sources of money like our recent gift or our budget leftovers from last month.


Scheming about how to pay for this vacation made me reflect on the ways I’ve paid for vacations in the past and other approaches as well.


Strategies for paying for vacations:

  • pick up additional work (overtime, side hustles)
  • save every month
  • use bonuses/gifts/found money
  • get someone else to pay for you
  • use debt


I’ve used all of these strategies except using debt (thank goodness!).


on our cruise vacation from 2008

I paid for a cruise vacation in 2008 through my side hustle as a clinical trial guinea pig (i.e. healthy volunteer).  As we are salaried and currently have no side hustles for which we control our rate of income, we can’t drum up money this way at the moment.


We now have a travel saving account that we fund every month and we also sometimes supplement this account with cash gifts and found money.  We’re paying for our Chicago trip through both these methods.  The savings account is how we pay for far and away the majority of our expense and it really reduces the stress of whether or not we can afford a vacation.  It works out well because we take small trips throughout the year so we’re fairly constantly spending money from it.


Last summer my parents paid for most of a vacation for our family (tickets to an event, hotel room, and some food, so we paid for only incidentals and other entertainment) and later this summer they are renting a beach house for our whole family.  Kyle and I are a little iffy on how we feel about being treated to these vacations as we view ourselves as financially independent from our parents.  My parents instructed us to view these family vacations as birthday gifts so that makes us feel better about it.


I think that if vacations are a regular part of your year, an every-month savings rate is the best way to make sure you can afford it when an opportunity presents itself.  But a vacation can also be a great motivator to hustle more for extra money or save found money/bonuses toward that purpose.


How did you pay for your last vacation and what is your preferred method?  Would you ever pay for a vacation with debt or let someone else pay for you?  Do you have any additional strategies for coming up with money for wants?


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24 Responses to "Strategies for Paying for Vacations"

  1. Daisy says:

    I have only ever paid for my vacations with money that SHOULD have gone into savings but didn’t. Other than that, I haven’t really taken many vacations, but I’m doing a side hustle for my NYC trip.
    Daisy recently posted..Tips for New Grads on Getting a Job

    1. Emily says:

      The money I hustled for my vacation in 2008 should have gone into savings because I didn’t have an emergency fund at the time. What’s your current side hustle?

  2. Emily too says:

    We usually pay for our vacations by planning and saving in advance – apart from our honeymoon, these have only been long weekend wedding trips, camping, or family visits, though. We’ve never done a long-distance vacation, which keeps costs down – our honeymoon was the most expensive because we stayed in B&Bs instead of camping, but we still stayed within a few hours’ driving distance and pretty much just chilled out.

    We’re saving a portion of our “found money” for a future big trip (or two?) pre-kids, though, and if we have any leftover in our tight budget this year that’ll be a priority. Also considering planning a vacation around a conference in a neat place this fall because if one of us is presenting, we can at least get that person’s flight and potentially some fraction of the lodging reimbursed.

    I think you shouldn’t feel bad about family wanting to help out with trips you take together. It’s a sign that they’re thrilled to be able to spend time with you, and as my dad said once, “We used to be in a position where things like this were a much bigger deal, and it is really rewarding to be able to do something that is small for us, but major for you.” (We don’t do family vacations but they sometimes like to help out with costs when I visit home, too.) There’s a difference between depending on your family and graciously accepting gifts – and what makes it a gift rather than dependence is that they’re excited to give it, and it’s not regular or expected. Your turn will come to help out your parents and your own children someday.

    1. Emily says:

      Our last big big vacation was our honeymoon too. I think we’ve only been gone for a week once since then, and that was to visit family and attend a wedding.

      That’s great that you’re saving already for a big pre-kids vacation! I have dreams of taking one but we’re not saving specifically yet. I love the conference-and-vacation combo opportunities that academia provides. So far we haven’t gotten to take any together but maybe we will before we graduate.

      Yes, my parents are definitely bribing us to spend time with them. 🙂 Last year was the first time they offered to pay for us to go on vacation with them so there isn’t an established pattern yet. We stopped going on family vacations around 2000 because all of us got so busy with summer activities so I think my parents are trying to resurrect that tradition.

  3. This is kind of an interesting circumstance that I wouldnt call totally a “vacation” – though it will still be at least partially one. I went to about 6 weddings last summer/fall, and considered very few of them to be vacations, but ended up leaving the state for all but 1 of them.
    The way I usually fund my vacations is to plan early and cash flow. For instance, if I know I want to go somewhere in december, I’d get the plane tickets with my spare cash from july’s paycheck, cover lodging with the august check, and then keep an eye on spending while on the trip for things like food, as not to go over my december cash flow. I’m sure this will get harder and harder, but for now, it’s worked fine.
    I think in 2013 will be the year that H and I establish a “vacation” savings account. (or I may go do it right now, who knows)
    Jeff @ Sustainable Life Blog recently posted..Lending Club Review

    1. Emily says:

      For the purposes of this article traveling to weddings would still be “vacation” although I probably should have called them trips instead. The vast majority of our trips are for weddings too, though probably not six in a year! That’s intense!

      Your cash flow plan is sort of what we do except that we do it out of a savings account. Particularly with trips that require flights, it’s straightforward to pay for them in stages, which helps with planning and funding.

      We didn’t establish a travel savings account until after we were married. Somehow paying for double travel on two incomes felt bigger than single travel on one income and we wanted more advance assurance that we could go. I love targeted savings accounts!

  4. reneeg says:

    We pay for vacations with…. all of the above! 🙂 (except debt…)

    I don’t think it’s odd or wrong to take parent-sponsored vacations. I think it’s a long-standing tradition and very common amongst families for the older generation to sponsor reunions or special dinners for their kids and kids-in-law – it’s probably their best chance at spending extended time with us!

    My dad was a pastor when we were growing up, and we didn’t have much money. My mom’s family lived on the east coast and we were in Seattle. My grandpa would fly my mom, me, and my brothers out each summer for a few weeks. By no means did this reflect poorly on my parents’ money management or financial independence.

    1. Emily says:

      We wouldn’t be able to take these vacations with my parents if they didn’t pay for us so it does buy them this special time with us. 🙂 And it’s really fun for us to do something other than attend weddings!

  5. I still haven’t paid for my own vacation yet because BF makes huge payments towards his loans each month. Even though I save each month towards my travel fund, I want to wait to go on a vacay with the BF. I can’t pressure him just yet, but he has promised that he will acquiesce if I take control of both of our finances, and make sure we are covering our bases. Right now we do our own separate finances but we know about the other’’s just that his priorities are not vacation saving, but more throwing towards debt =( I told him after I graduate law school, we will deserve a vacay. He agreed, so I’m really looking forward to it.

    Just gotta keep truckin’!
    From Shopping to Saving recently posted..PF Link Love: Fave Reads of the Week, The I Have 2 Dads Edition

    1. Emily says:

      That’s a long time to wait for a vacation! Are you sure you won’t be taking some in between school and internships? My observation of my law/professional school classmates is that they go on vacation 2-4 times as much as I do! Sounds like your boyfriend is intent on paying down his debt – that’s great!

    2. Emily too says:

      Aw, hang in there…it says good things for your future that you don’t want to go without him and he’s trying to be as responsible as possible, even if it’s frustrating right now. It’s great that you’ve got something to look forward to, hope it isn’t too far away!

  6. Vacations have kept me from paying my debts off as fast as I can. I have definitely taken my parents up on offers to pay for airfare, and in the past, have paid for vacations on my credit card. No more! I’m only planning one trip this year, and that’ll be not too long after my student loans are paid off, so I’ll delay upping my car payment in order to have a little cash.
    Kathleen @ Frugal Portland recently posted..What’s the difference between banks and credit unions?

    1. Emily says:

      What a great reward for killing your student loans! It’s nice to get a reward to rejuvenate you to pay off the rest of your debt.

  7. We pay for our vacations by saving for them all year, setting a budget, and finding vacations that fit within that budget. This is the first year that we have felt financially confident enough to take two long beach vacations on top of several small weekend trips.

    I would definitely not suggest that a person go into debt to fund a vacation. If you cannot afford to pay cash for your vacation, you cannot afford it. Period.

    I also go on vacation with my parents every year. It is a great bonding experience between my parents and children (ages 1 and 3) and creates some wonderful memories. Although I see this as a way to spread out the vacation expense, I would not feel comfortable letting my parents pay. As an adult with my own person finances, I would feel like a big “mooch.” I wouldn’t be proud if I took advantage of my parent’s generosity. We generally rent a beach front condo and split the cost 50/50.

    1. Emily says:

      I agree with your sentiments about debt and vacations… and debt and anything that’s not an investment!

      I hope that by the time we have kids we’ll be paying our own way for vacations, too. I guess for now we’re playing the poor student card. 🙂

  8. Michelle says:

    I usually use side income for my vacations. Blog income, mystery shopping and taking surveys have been helpful.
    Michelle recently posted..Get to know me!

    1. Emily says:

      That sounds like a good plan. Extra work for extra fun.

  9. You have done some very interesting side hustles that is for sure. We actually build our vacation into our budget so each month a certain amount of money is set aside. It works out pretty good and we don’t have to work extra to make it happen.
    Miss T @ Prairie Eco-Thrifter recently posted..Reader Question: How Much Money Do I Need To Buy My First Home?

    1. Emily says:

      I agree that strategy works out well! Now that our budget is more mature that is what we prefer.

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