10 Ways To Make The Most Of Your Vacation Time

Want to milk your vacation time for all it's worth? Even if you only have two weeks? These 10 travel tips are a mix of flight booking hacks, destination suggestions, and mindset shifts. Great for the 9-to-5-er or anyone who wants to travel more but doesn't have time >> yesandyes.org
American friends, this is not where I torture you with statistics about how much vacation time Europeans get.


While I have pretty much unlimited “vacation time” (re: writing blog posts at a different table, in a different time zone), my husband does not. I do a lot of solo travel but sometimes it’s nice to travel with your sweetie, so we’ve had to get preeeeetty creative about milking those two measly weeks for all they’re worth.

And we’ve gotten pretty good at it! Here 10 tricks you can use to make the most of your vacation time – no matter how much you get!

Actually understand your vacation benefits

This seems painfully obvious, but when I worked for other people I, um, could never quite get this nailed down. Rather, I had a vague understanding of how much time I had off (NEVER ENOUGH) but I didn’t really understand how it accrued and what happened to it come December 31st. The end result being, of course, that I didn’t use it all.

So pull out that employee manual you never looked at, review your contract or make an appointment with HR. Here some things to consider:

  • How many vacation days, personal days, floating holidays, and sick days do you get? And what are the requirements?
  • How many vacation days do you earn per year? And does that accrual rate change when you’ve been there longer?
  • Do your days off accrue based on when you started or the 1st of the year?
  • Are you allowed to take half days?
  • Are you allowed to occasionally reconfigure your work days – work four, 10-hour days so you can take one day off without dipping into your vacation time?
  • What’s the process to request time off?
  • Can you ‘roll over’ your time off into the next year?
  • How much are you allowed to take off at a time? Can you take off all 10 days in one big chunk?

Start scheduling + planning your vacation now

Did you know we get most of the joy from our vacations before we even take them?! Let’s take advantage of those pre-vacation travel vibes.

What if you opened up your calendar at the beginning of the year and started to plan out your time off? A week in the Florida Keys in February, a four-day weekend in June, a half-day in April, a half-day in August, a three-day weekend in September, everything else for the holidays. Literally block those days off on your calendar.

Start a Pinterest board, if that’s how you roll. Mentally assemble the perfect travel wardrobe. Research the best bars and restaurants, obsess over Airbnbs. If you’re planning a staycation, make a reservation at a restaurant you’ve been meaning to try or look up all the must-sees in your own city that you haven’t seen.

Sidenote: Here are my favorite free/cheap things to do in Minneapolis and here’s $25 credit towards your first Airbnb booking!

Try a mix of ‘vacation’ and ‘travel’

To me, travel and vacation are two very different animals; equally furry, equally valid. Travel means different cultures, different foods, navigating unknown cities on public transport, getting outside of my comfort zone and maybe getting a few new stamps in my passport. I’m exploring! I’m learning! I probably return home inspired and slightly exhausted!

Vacation means sleeping waaaaay in, poking around one city, eating in lots of restaurants, seeing lots of movies, wearing lots of tunics and sundresses. I’m not challenging myself because I’m relaxing, you guys. I return from my vacation calm and well-rested and maybe tan.

When you’ve got two weeks out of 52 to get away from work, I think it’s important to mix it up. If you spend all your vacation time backpacking around Vietnam, you’ll probably return a bit worn down. But if you go to the same timeshare in Boca every year, you probably won’t reap the psychological or emotional benefits that come from pushing your personal envelope.

How you spend your vacation time is, of course, an incredibly personal choice but if you find yourself exhausted or uninspired by your usual choices, maybe it’s time to try a bit more travel or a bit less vacation.

Get INCREDIBLY strategic with how you use your time

I mean Neo-level time-hacking.

Like, you work four, 10-hour days and take a red-eye from Minneapolis to Anchorage on a Thursday night. You spend the next 10 days ogling bears and glaciers and wild flowers and then take the red-eye back to Minneapolis on Sunday night. Sleep on the plane, show up to work (slightly) late on Monday, and stay late on Tuesday to make up for it. That’s 10 days of vacation for 5 days of PTO!

Or if you’re not into red eyes + coffee, try: weekend + Martin Luther King Jr. Day + 4 days of PTO + weekend = 9 day vacation that only requires 4 days of PTO. You can also try working from home on your departure/arrival days or working half-days to accommodate flight times.

P.S. There really is a direct red-eye from Minneapolis to Anchorage and it’s $500 in the winter! I took it when I went to the Iditarod and it was amazing!

If possible, take a really early, direct flight

Yes, it totally sucks to get up at 4 am to catch an 7:30 flight but when you land at your destination before noon, you’ll be so, so glad you did! When you take an early flight you can enjoy the three-day aspect of those three-days-and-two-nights vacations.

Pro tip: take a really early Saturday flight; they’re a) cheap b) that’s one less night of hotel to pay for!

Go places you can get to quickly and directly (and then stay there)

Few of us enjoy the transportation part of the travel – the never-ending taxis and buses and trains. That’s not relaxing! That’s not how we want to spend our hard-earned PTO!

If you’re heading to a remote fishing village in Mexico, you’re probably looking at 14 hours of travel from door to door. But if you’re flying from Chicago to New Orleans, you can go from bedroom to hotel room in four-ish hours. You don’t even have to stay in the U.S.; you can leave Minneapolis at 8 am and be in Iceland by 3 pm!

When you’re looking at flights and prices, factor in the value of your time. 30-minute layover? Sure. Five-hour layover? That effectively eats up one whole day on either side of your vacation. Is it really worth saving $50?

Take more long weekends + half days

I totally advocate for slow, long-term travel but that’s not always possible. And if you take two-week vacations every single year, you might just spend the other 50 weeks hating your life and job.

We get more joy and relaxation from small, frequent breaks than we do from one, enormous break. If you work in a particularly high-stress industry or have kids, several long weekends (while the kids are at school) or half-days might be a lot more rejuvenating than a week in Disneyland.

Once you’re on your vacation – really, actually vacation

Turn on your out-of-office reply. Delete email from you phone. Hell, leave your phone on the bedside table when you head down to the pool! If someone tries to talk to you about work or repainting the deck or training the puppy – shush them with a margarita. Leave the self-development and business books at home and give yourself over to novels and comedy podcasts.

Vacation is a mindset, y’all. If you play it right, a half-day spent in your backyard with a pile of magazines can be just as restorative as a week in Tulum.

Stay ‘in’ your vacation, even on the last day

I don’t know about you, but I spend the last 1.5 days of any vacation emotionally preparing for the return trip. I’m worrying about what we’ll have to eat when we get home, wondering when we can pick up the dog, and quietly dreading the pile of mail in the porch. That’s 36 hours of vacation time that I’m wasting!

Instead, I’ve started to make a concerted effort to stay ‘in’ my vacation until the last possible moment. Sometimes that means a fancy breakfast at a sweet cafe before our flight or getting an early-morning massage. Sometimes that’s taking one last walk around the neighborhood where we stayed or reading a novel on the flight home. It’s hard but doable!

Make your ‘re-entry’ as humane as possible

It’s easier to enjoy our vacations if we know we’re returning to a (relatively) clean, sane, organized life. If possible, leave your home clean – fresh sheets on the bed, laundry done, dishwasher and trash cans empty.

Make sure you have a few things in your freezer or cupboard you can eat when you get home so you don’t have to worry about grocery shopping. You can even sneakily leave your out-of-office reply up for an extra day to manage client and co-worker expectations.

But I want to hear from you, fellow Americans-who-travel-with-limited-amounts-of-vacation-time! How do you do it? Share your best travel hacks in the comments!

P.S. 7 travel tools I will not shut up about till you buy them + 11 cheap travel tips that helped me travel for 10 months on $5,000

photos by Annie Spratt and Dan Gold // cc

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  1. Cristin

    Aw dude this is totally my jam!
    Last year I had the Southwest Companion Pass but limited vacation time, and managed to squeeze in:

    – Miami on MLK weekend (early Sat-Mon, no PTO)
    – Austin for my birthday in March (Fri-Sun 1 day PTO)
    – Playa Del Carmen, Mexico for my honeymoon (Sunday- following Monday, which was Memorial Day, so only 5 days PTO)
    – Las Vegas for Halloween (Fri – Sun, 1 day PTO)
    – Miami again in December (Thurs- Sun, 2 days PTO)

    If I had to pay for all the flights in cash I would not have gone so crazy, but since they were free I figured it was almost more wasteful NOT to go 😉

    • Sarah

      I am so impressed!

  2. Amy Kennedy Fosseen

    Oh my gosh, I suck at this! Well, I guess I’m pretty good with adding on to holidays, but I never do anything, I’m usually just so excited to not be going to work that I stay home and create projects for myself, like painting the bathroom. And I have vacation time! It rolls over, I have over 180 hours–over four weeks! But this has inspired me–not sure what I’ll do, but I’m going to do something. Even if it’s visiting one cool Minnesota thing a month.

  3. Diana

    Leverage work travel and conferences into mini-getaways. If attendance at these conferences are required for work then the company will pay for the travel and often the “official” hotel. These things generally take place mid-week so you’re already at the place on Thursday afternoon, make it your long weekend from there until Sunday night. Once the conference wraps, leave the business traveler hotel and check into a cheaper Airbnb on a bus line and you’re looking at the same town from a totally different point of view. At most, you might have to cover any flight cost differences for the Sunday evening flight. I’ve done this with wild success in Santa Fe, San Diego, Phoenix and Boise.

    • Sarah Von Bargen

      Yessss! I did this last year in San Diego!

    • Jamie

      Yess I LOVE doing this. Last year I got long weekends in London and Stockholm and didn’t have to pay for the flights. Not having saved up a bunch of money for the trip or using PTO also takes a little of the pressure off–I rather lazily but fully enjoyed both cities!

      I work from home, and get a decent chunk of vacation, am expected to be “at my desk” fairly regular hours each day, and my husband works in an office. We’ll often join each other on business trips as well, as this means we only have to pay for one flight and at least part of the hotel is covered.

      • Jamie

        Also–I LOVE working 9 hours Monday-Thursday, then take a half day Friday to leave early for a weekend away and not use any PTO (even if I’m not going away, if I have guests that weekend or am just looking forward to some staycation time, it can be nice to take off early on a Friday).

  4. Amy Morris

    My favorite trick is to wrap vacations around a weekend and work a few extra hours each week so that I only have to take 5-6 hours PTO for each day off. Every bit helps! I just returned from 4 days in San Francisco with my best friend of 20+ years and I totally agree that the anticipation is almost better than the actual vacation. Time to start planning my next jaunt: New Orleans!

  5. Missy D

    It still boggles me how little holiday leave North Americans get… in Australia we get four weeks a year and I feel like that is not enough! 😉

    I also like to strategically plan my holidays around public holidays so you can have even longer leave without eating into your holiday leave balance.

  6. Ali

    I’m like you in that I can *technically* take vacation whenever I want, though it never really works out that way. I remember having limited vacation time when I worked a traditional office time, and even though I was lucky to have 3 weeks vacation time (plus 2 personal days!) I still squeezed every ounce of travel time as I could by using holidays and crazy flights. One year I took 3 weeks off in January/February to do an Antarctica cruise with a friend, but since I rolled over a couple days from the previous year, I was still able to go to Malta and Dubrovnik in the summer…though my boss WOULD NOT let me have one more day unpaid or make up the time so I could take the entire week, so I flew out Friday night and had to be back at work the following Friday. The next year I managed two weeks to Hong Kong and Australia, a long weekend in San Francisco, a week in Quito, and a long Thanksgiving weekend in Prague. And I definitely agree about the planning part – I LOVE planning trips!


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