Tales from the Wallet: What’s Your Vacation Money Strategy?

vacation money strategy tips and tricksHere’s a fun question for today: what’s your vacation money strategy? What’s your overall strategy about vacations and budgets — how do you plan to budget while on vacation — and how do you pay for vacation? There are a lot of questions here, such as:

  • Overall vacation money strategy: What do you consider getting the most “bang for your buck” — frequent and small vacations, one big vacation every year or two, or something else? From the “time vs money” perspective for vacations, do you gravitate towards the more expensive but all-inclusive cruise, resort, or tour so that you save time at the research phase — or do you prefer (for money or enjoyment) to DIY your vacations? For those of you who go to the same place often (such as spending a week every summer at Cape Cod or the Jersey Shore, or heading to DisneyWorld once a year), how big of a role does budgeting play in that decision?
  • Budgeting while on vacation: do you have ways of saving money while on vacation that you use no matter where you go? For example, bringing protein bars with you so your breakfast is covered, or making sure to hit the “included breakfast” at your hotel and eat a ton so you don’t have to eat a big lunch?
  • How to pay for vacation: Do you save in advance for your trip, or put it on credit card? Does anyone use automatic transfers to savings to set aside money regularly to keep for vacations? Is anyone heavily into airline miles or points?


Pictured at top: Love this Marc Jacobs wallet, now marked 33% off as part of the ongoing Nordstrom Half-Yearly Sale! (Affiliate links.) See our workwear roundup as well as our accessory roundup.)

For my $.02, I am lousy at planning vacations for my family, and I wasn’t so hot at it before I was married with kids either. I’ve gone to Paris in August (don’t), left major research like day trips out of town for the last minute… and in general we just haven’t gone on vacation a lot. Before I was married, my work schedule was so prohibitive that the idea of planning a “big vacation” was difficult and fraught with stress (what if something came up at the last minute? would someone come with me, or would I be traveling solo? if I talked a friend into coming with me and then work prevented me from going, how pissed would the friend be?) — so instead I tried to get away whenever I had a weekend free, and made a lot of small trips.  (I wished I’d known about some of these vacation packages for busy women back then!)  Nowadays, with two kids who have to be in bed by 8 PM every night, one of whom is still napping for 1-3 hours at midday, it’s harder logistically to think about getting away anywhere — packing the gear alone is overwhelming. (We actually did a roundup over at CorporetteMoms of companies that rent baby gear like strollers, so you don’t have to pack/bring your own.) We’ve also done AirBnB with kids, but that comes with its own challenges. So I keep gravitating towards an all-inclusive vacation or resort — but we haven’t bit yet. (Here’s an older post with reader advice on how to plan a vacation, as well as an older discussion on how to take vacation without losing your mind.)

As far as how to stay on budget on vacation, I am definitely one of those people who brings enough protein bars (or beef jerky packets, or even peanut butter packets when in a pinch) that I don’t have to worry about breakfast. I also try to take any free apple I see offered (such as at the hotel concierge desk), I try to reuse water bottles wherever possible, and I try when possible to only eat “one big meal out,” both for the caloric budget as well as the monetary budget. I’ve brought library books on vacation with me rather than get sucked in at the airport bookstore, and I’ve gotten audiobooks and comedy CDs out of the library ahead of time also for road trips. (In some library systems, if not most, you can also check them out via Overdrive or whatever digital collection service your library uses.)

We do automatic transfers for vacation savings, though — we have a special account in Ally for vacation money; at times we’ve moved as little as $20 a month over. This serves dual purposes for me: the first purpose to our vacation savings account is to actually save money for vacation and having a dedicated stash so I don’t freak out when the credit card bill comes in and is so much higher than it normally is — I just move over the money from that dedicated account so I can pay the credit card bill off in full like I normally do. The second purpose is an element of shaming myself — if the account grows too large I know it’s high time time for the family to go on vacation!

While I am not into the points game (I like my Amazon credit card too much and stink at planning vacations to switch to a card for mileage points!), one of my best friends, J, recently got into the whole airline miles/points issue through his boyfriend, N. J had never traveled extensively or gamed the system, but N is an expert at it! They just got back from an awesome trip to Japan (from NYC) that would have cost $20K but instead cost them pennies — and they’re already making plans to go again.  Color me impressed!

Readers, what’s your vacation money strategy? What’s your overall vacation strategy? How do you pay for your vacations? How do you stick to a budget while on vacation? 

Social media image credit: Stencil.vacation money strategy tips and tricks for busy women


  1. MM.Lafleur WTH? :

    I finally ordered an MM. Lafleur dress, the Etsuko in olive… and was shocked it wasn’t lined. The shoulders were also nightmarishly poorly constructed… but what really got me was the gall to charge $195 and up for a thin, un-lined dress.

    Here’s a start-up idea: stop.cutting.corners.and.being.cheap

    • Anonymous :

      Shrug. It’s a dress that is meant to stretch (hence the spandex). That’s not the type of dress I would expect to have a lining.

    • Marshmallow :

      Right… I wouldn’t want a lining in my Etsuko dress (or in most dresses, frankly). Linings are hot and non-stretchy.

    • Anonymous :

      A stretchy synthetic dress like this doesn’t need a lining, but I do think the Etsuko is MM’s worst item. I own and love several of their other styles, but I don’t like the cut of the Etsuko and I do think it looks cheap.

    • Question about this dress: In all of the pictures it’s styled with a belt. Does that come with it?

    • I actually prefer the lack of lining. You can’t machine wash a dress with lining.

      • Anonymous :

        Uh…sure you can. Occasionally, some lining fabrics can be wonky with wet wash, but it’s not an automatic disqualifier or anything.

  2. Anonymous :

    I have a rough idea of the amount of money we can spend on travel per year, but generally we travel as much as time will allow, and we don’t stick to a strict budget. This usually works out to one or two week-long (sometimes one two week-long) international vacations and four to six long weekends within the US (usually at least a couple of those are for family obligations or weddings). I’m not a hotel snob and I generally try to find affordable hotels (although I will pay for cleanliness and location when necessary and we’ve occasionally done vacations that were built around an expensive hotel, like an overwater bungalow in French Polynesia). We generally go to whatever destination we want don’t worry about food and activity spending while we’re there.

    We don’t save specifically for travel, we just put a good chunk of the money that’s leftover after our bills and savings towards it. Travel is our #1 indulgence though and it’s the only fun thing we drop serious cash on.

    I get a great deal out of enjoyment of traveling planning, so we tend to avoid cruises and all-inclusive resorts although we have done them on occasion when they seemed like the best option for seeing a particular place – glacier cruise in Alaska, adults-only all-inclusive in Mexico for a couples getaway – and enjoyed them.

    • This makes me feel better because my answer was…we don’t save for vacations, we kind of just go and spend whatever it takes to get to our base level of comfort.

      • Same here – our main limit is time, not money, although our inherent sense of self-control prevents us from dropping $25K on a luxury safari!

      • Same.

        Though to some extent the choice of destinations is a form of budgeting. This year we’re taking a big trip to Aus/NZ and the tickets alone are exorbitant. We can’t do that kind of thing two years in a row though. Next year’s vacation will just be someplace we know will cost less to get to/be (possibly somewhere within the US or driveable). Either way, once to the vacation spot we try to just be comfortable without being luxurious, see and do things that are reasonably priced, and don’t worry excessively about sticking to a specific daily budget.

    • You are very smart. My philosophy is to FIRST convince the manageing partner that he can do WITHOUT me for at least a week. So far I have onley been abel to do this 2x in the 8 years I have been doing this. Once I get over this hump, I next have to pick a week. This year, I am workeing on having off between the end of August and the Beginning of Sepetember, includeing Labor day. I want to spend time in the Hamton’s once the peeople leave and I do NOT have so many peeople stareing at me. Dad says after Labor day, all of the leches will be back at work. YAY! I do not want a lech stareing at me, or worse! FOOEY!

      So if I get the week off, I will ask Dad to prepay for as many expenses as I can have ahead of time, so that I do NOT have to deal with cash or credit cards or worse yet, traveler’s checks! DOUBEL FOOEY! Once he pays for my hotel and food and incindentals, I should ONLEY have to pay for impulse purchases, which I will keep to a mimimum, since I am now saveing for a 3 bedroom apartement. Dad has his eye on a new place, but it is on the WEST side. FOOEY! He says I can get more value for my money, but that would mean I will have to go crosstown to get the Subway. DOUBEL FOOEY! He says I should be walking anyway. FOOEY on that, especialy in the winter! I will not freeze my tuchus off just to keep him happy, but he wants a free place to stay when he and mom come into the City. That is fine, but it will NOT be deducteable by me, he says. FOOEY!

    • Anonymous :

      Same. The thing limiting us from traveling is time, not money, so we don’t budget or set aside amounts. We go as often as we can and then spend what we want.

  3. My 2 cents:

    – Prefer to take 1-2 longer (1 or 1.5 week) trips per year, with 1-2 long weekends as well. If we only have the time or budget for 1 long trip, it is definitely going to be a beach-based vacation.
    – Although it doesn’t technically matter since we don’t live paycheck to paycheck and pay off our credit card in full each month, it feels better psychologically to split up the bigger expenses, so for bigger trips, we’ll book flights in a different credit card cycle than making our hotel deposit.
    – We like to travel *just* off peak. Caribbean in January or February is cheaper and less crowded than December or March, but you still get the benefit of ideal weather. We tried an “off season” vacation once (Turks in November) and it was a rainy mess and some restaurants were closed… no sense saving money to be stuck indoors on a beach trip.
    – We pay attention to spending on food, but aren’t ridiculous about it. We’ll plan for 1-2 “fancy” ($150-200) dinners for a 1.5 week trip, and otherwise keep lunches under $50 for 2 and dinners under $100 for 2.
    – If a fancy restaurant is also open for lunch, you can often enjoy many of the same options for less money.
    – We venture into grocery stores and buy local breads, pastries, fruits, yogurts, etc. for breakfast, and local spirits/mixers/cocktail snacks for a drink before dinner.
    – We DON’T try to budget by bringing food from home. I can eat Belvita biscuits at my desk every day; bringing that memory with me onto my ocean view terrace is NOT going to happen.
    – If spending extra money is going to afford us more time to enjoy our trip or less hassle when traveling, we will usually do it (within reason) – e.g., spending a little more to get a direct flight or an earlier/later flight.

  4. My partner and I have a joint account specifically for travel. We both have automatic transfers set up each month to fund our travel. We found that this is the best way for us, that way when we see a great deal, the money is already there and set aside for it.

    We don’t usually have our hearts set on any specific place or time, we just keep an eye out on the travel deal websites and whenever we see a deal that we cannot resist for a place we are both interested in, we book it. I have found that this saves us a lot of money since we are much more flexible. I have also done deals where you don’t know the resort or hotel you will be staying at until after you book- this is a huge money saver and has not failed me yet (just read all the fine print)

    We usually do not worry too much about what we spend while we are there, it helps that neither of us do much shopping. But we limit ourselves to only 1 or 2 nice dinners. I also (more out of convenience then cost) have no shame in bringing a jar of peanut butter and buying a loaf of bread when we get there for breakfast/lunch/snack

    This works out that we are able to do 1 or 2, 1 week international vacations each year and a few long weekends

    • givemyregards :

      Very similar approach except my SO and I have separate savings accounts. What travel deal websites do you like?

      • I check TravelZoo and The Flight Deal the most. But I also have used Cheap Caribbean, European Destinations and Groupon. What are your favorites?

        • givemyregards :

          I also like the Flight Deal, but my SO’s schedule is not at all flexible – he gets a lot of time off throughout the year but cannot otherwise take vacation days – so I’m not able to take advantage of their offerings as much as I’d like. When I’m bored, I like to lazily browse Kayak’s explore feature and other sites to research potential places I’d like to visit so that I have a general idea of how much it costs to travel there (and during which times) that I can keep in mind when we do have free weeks that come up. I also like the Travel Codex blog. They’re mostly about getting the most out of miles, etc. – a game that I don’t play much – but they often link to other sites or alert me to sales I wouldn’t have otherwise known about. Oh, and I book a lot of hotels through Mr and Mrs Smith. They’re not bargain basement cheap, but they usually have the same price as other places (and if you find the room cheaper elsewhere you get $50 towards a future booking) and I like their little booking perks, usually a free glass of wine or breakfast each day.

          I forgot that Groupon does travel, but I have a credit with them from their class action suit, so I’ll have to check them out!

      • I have found some terrific deals on Scott;s travel newsletter. The places are very random, but that makes it fun.

  5. Planning for vacations extends the fun of the trip for me & my partner. We try to go to Europe once a year & maybe one tropical (Hawaii/Caribbean) or smaller U.S. trip each year, & travel is what our savings (x amount per paycheck, automatic deduction) & credit cards are for. We prefer to stay in one place for a week or more, rent an apartment, get groceries to make breakfasts/lunches, & splurge on dinners. Then it’s all sightseeing & relaxing.

    • I’m chuckling that Hawaii is lumped with the “smaller trips”. My husband and I are saving to be able to go to Hawaii for our 10 year anniversary (several years away…). We love travel but have not gone anywhere fancy since kids.

  6. TO Lawyer :

    I transfer money out of each paycheck that’s sitting in a travel account but it’s accumulating because I haven’t been anywhere in a while.

    I do have one trick for fun money on vacation – I try to use the US ebates (instead of the Canadian one) wherever possible. When I get those checks, I put them in a separate USD account so when I’m going on vacation, I just withdraw that money. It’s not a ton of money but usually is a little bit of extra fun money.

  7. LadyLitigator :

    I try to use my own credit card for work trips (now use the Chase Sapphire Reserve) so I can accumulate points to use on personal travel. I get reimbursed in full, so the benefits are great. Some firms have a policy against this; mine does not. If a client flies me two or three times a year business class, that earns me enough points to get round trip coach tickets for vacations – plus frequent flier status that means I don’t have to stand in line, etc. Once you get higher level frequent flier status, you accumulate points faster. I also work points to make sure that I get credit card points AND airline points for every paid trip I take. To give you an idea of how quickly this pays off, I will take three international vacations this year, and pay less than $1000 total for flights for me and hubby.

  8. Anonymous :

    My job averages about 20% travel, sometimes more and sometimes less. For the past several years, much of this travel has involved relatively short flights or has been by car. I am generally loyal to one airline, but stay at multiple hotel brands depending on the destination. I use airmiles and hotel points to help cover family travel.

    We have a regular “points” credit card, not an airline card, that allows us to use points to purchase airline tickets or transfer points to any frequent flyer program. We use this card to pay for everything. Between the credit card points and the relatively modest number of airline miles I rack up every year on business travel, we are usually able to cover plane tickets for our entire family for a vacation every other year, plus one or two solo trips a year for my husband or kid.

    I used to do pretty well with hotel points and free nights earned through Marriott’s MegaBonus program, but MegaBonus has gotten a lot stingier (no more free night earned after two stays) and the point requirements for hotel reward redemptions have gone up. Several years ago I was able to cover entire vacations with hotel points. Now I typically get a couple of free nights per year, which we use for weekend getaways or kid sports trips.

  9. The perfect cardigan :

    I have this problem with all my cardigans- by the end of the day the sleeves and elbows are all stretched out and the cardigan looks like a mess. I suspect this is because I am buying fully cotton pieces. Any suggestions for synthetics that look modern, clean lines and won’t stretch out beyond recognition?

    I swear I am not arm wrestling or anything weirdly strenuous!

    • look for something with spandex in it

    • I’m currently wearing the August Silk Crew-Neck Cardigan from Macy’s and I love it for just the reason you described- it keeps its shape and looks sleek all day. That said, it is a very traditional cardigan, so the cut itself isn’t all that modern, but sometimes all I want is a reliable basic.

      • Link to cardigan described above

      • August Silk cardigans are my favorite. Stumbled into them by accident, but they are so soft, lay smoothly over clothes and keep their shape.

    • Anonymous :

      Maybe not ideal for summer, but look for a wool blend. Uniqlo has super thin merino cardigans that I wear during summer.

  10. I budget $500 a month for vacation (usually ends up being in the $6k/year range) and typically take 2 one-week international vacations, fly to visit family over the winter holidays, and probably 8 domestic weekend trips a year. I use Scott’s Cheap Flights for cheap airfare. For lodging, I stay with friends/family, or in AirBnbs, or occasionally in cheaper hotels (even a hostel if I know it’s a good one and I can have my own room).

    I tend to prefer to take lots of vacations and not spend tons of money. I use the Chase Sapphire Reserve card for everything and will book travel through their portal when I have enough points. My travel budget covers transportation and lodging. Food and activities gets built into my regular budget. I eat out a lot when I’m in my home city, so eating out at nice places on vacation doesn’t make much of a difference. The big difference I’ve seen between my travel spending and friends of mine is that I don’t like to spend much on lodging (I want it to be well-located, clean, and don’t otherwise care about the niceties), and I don’t do expensive activities, so I’m able to do lots of travel for not much money.

  11. MissJackson :

    I feel like a little bit of a jerk, but saying that I budget for vacations is a bit misleading. I take approx 15k from my yearly bonus and we typically plan one big (two week, international, luxury) vacation using that money from the prior year – that way we can plan ahead of time and I don’t have to worry about “what will this year’s bonus be?!?” If what we want to do costs more than that, we still tend to just do it and pay for it with slack in our budget. We take a few smaller trips throughout the year (long weekends usually) that I don’t budget for at all, but we have sufficient buffer in our monthly income to just pay for these as we go. This was a much bigger challenge a decade ago when we were on a tighter budget. Now, vacations are basically our biggest joy, and we’re willing to spend a good deal and enjoy ourselves. We have a relatively cheap mortgage and only one (cheap, paid for) car. So we pick and choose our extravagance, and vacation is basically #1 on that list. It’s also easier to get away for 2 weeks as in-house counsel than when I was in BigLaw (those were some very dark, vacationless times!) In-house I’m still more limited by my vacation days than by money so I don’t worry about it too much. I should say that this is clearly easier as a couple than as s family because I can see how we might have to actually consider costs if there were 3 or 4 of us instead of 2.

  12. My vacation money strategy is to not go on any until my student loans are paid off.

    *mic drop*

    January 1, 2018 will begin my new life of doing what I want with my money because I won’t be beholden to anyone!

  13. I’m single and childless, so I can be a bit more flexible than someone with a family.

    I don’t really specifically budget for travel. I live in one of the most expensive places to fly from in the country, so I know there is no such thing as a “cheap flight” for me – minimum $300 no matter what. I tend to plan things well in advance though, so I’m booking the flight and paying it off well before the trip. Then I’ll book an AirBnB and pay for that before the trip too. Spreading the charges over several months is kinda like budgeting, right?

    I tend to take 4-5 long weekend vacations most years, and I try to take an international one every 2-3 years (hoping to increase this frequency as my salary increases). For a lot of the long weekends, I will plan to stay with friends so I’m not paying for lodging. If I am paying for lodging, AirBnB is my first choice (especially if I can split it with friends). That makes it easier to save by eating breakfast and maybe a couple other meals in. I’m pretty low-maintenance when it comes to hotels, as well. My splurges tend to be on activities and a few nice meals – those are the things I’ll remember from the trip, not how nice the hotel was.

    I’m currently planning a 2 week trip to Europe with my sibling and cousins, so we’ll see how well my spend vs. splurge preferences mesh with theirs. I get almost as much joy from planning a trip as from taking it, so they’ve kindly let me take the wheel . The idea of a cruise or group tour sounds miserable to me – I highly value freedom when traveling.

  14. Travel is our biggest indulgence. We spent 10% of our annual take-home pay (after insurance premiums and other pretax allocations) on travel in the past calendar year. We have automatic drafts from our main account that receives our direct deposits to a Weekender account and also a Major Vacation account. Our income is co-mingled and all our accounts are shared. I plan almost all our vacations. Family of four. We tend to stay in mid-range hotels with the occasional splurge hotel. For example, we stayed at the El Conquistador in an oceanfront room for a few nights while in Puerto Rico but then we also did an interior statement on the cruise ship that left from Puerto Rico to balance out the spending on that trip.

    I travel for work about 20% so I do rack up reward points on my credit card which helps. (I have to submit all my business travel for reimbursement; don’t have a corporate card.)

    Generally we do one international vacation per year, one east coast beach trip per year, and a bunch of extended weekend trips (driving or train). However, historically our international trips are to the Caribbean islands — not Europe, Asia, or anywhere far flung. We are hoping to travel further in the years ahead.

  15. Even cards that are merely thick cardboard slide in and out with ease. The bifold section is also sized right with two compartments to separate smaller from larger paper money, or money from checks, or any other combination you might desire.https://www.amazon.com/dp/B00SHORFYA

  16. I’m married with 1 child, another on the way working at an in-house job with regular hours.

    Before kids my husband and I travelled quite a bit. We would do 4-5 day vacations about 4 times a year. The strategy then was to tag a couple PTO days on to a long weekend, and we also travelled off-season and got a lot of really good affordable trips in that way. We generally AirBnB, and do a mix of dining out and our own cooking. The trips were adorable enough we didn’t need to save for them.

    Before in house I worked at a firm, and real vacations were simply not possible. Every “vacation” was hampered by a client emergency so I would end up working on my laptop.

    Traveling with a baby has been interesting. We did 2 international trips with our son when he was under 1. * nightmarez * On the first one, he started teething and cried all night our first night at the hotel. On the second trip, he was so antsy on my lap in the plane, he rolled around and cried and threw things… at a poor sleeping passenger next to us! ugh. We did one domestic beach trip without him and it was enjoyable but we spent a lot of time missing him. New strategy is going to be road trips only for a while unless it’s without the kids. We bought an SUV.

  17. MidwestEngineeringManager :

    We have 2 LOs and live near a really small (bad) airport…. We travel about 3x/year for about 1 week with flights and nearly always rent a house through airbnb or vrbo. We have stayed at amazing places in great neighborhoods. We love to walk to dinner, have a leisurely breakfast at ‘home’ etc… Or just have a nice dinner at ‘home’ with a splurge bottle of wine while the LOs watch a movie or play games or whatever…. This last vacay we used Turo for a car too…. a Tesla X for extra fun! We don’t budget for them, but we do plan ahead to fit with school schedules and ensure flights are available to get out of town. I also try to have the ‘next vacation’ planned before my current one is done…. then I have something to look forward to when work gets rough. :)

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