9 Ways to Stretch your Vacation Days that Really Work

21 August 2015

We try to travel as much as we can. For me, that means taking six domestic and international trips so far this year, with two more still coming. When we post new articles about the latest lands we've traversed, our friends often ask us how we can travel so often and still maintain careers with limited time-off policies.

The truth is, when you only have 10-15 business days at your disposal, you have to get creative. Here are some of the things we do to stretch our vacation days as far as we possibly can.

This is surprisingly important, especially now that we've both reached an age where travel for things like weddings and baby showers can easily take up a week of paid time off (PTO) alone. Caileigh also has to account for a few days each year to visit home. Your company might provide you with this, but early on in my career, I created a vacation day tracker that enabled me to strategically allocate my time off as needed throughout the year.

Typically, I try to roughly plan out my time off for the year before the end of February, even if I don't have dates fully locked down. I know that I need a break at the end of each season, so I plan to have time off -- whether just a long weekend or a full-fledged trip -- around March/April, August/September and the winter holidays. Once I've accounted for the essentials (weddings, moving, visits home, and so on), I assess how many vacation days I have left that I can use toward trips I want to take and plan it out in accordance with these time frames.

We know this can be controversial when you're trying to travel on the cheap because holidays usually mean inflated rates. This is another reason to plan ahead so that you don't blow your entire travel budget on your inaugural voyage. But by treating holidays as bonus vacation days, you can increase your yearly allotted time off. For example, if you want to travel for 10 days leaving on a Friday and arriving home the following Sunday, traveling over a three-day holiday weekend means you'll only have to take four vacation days. BAM.

If cost is still a concern for you, consider ways you can leverage some holidays that are lesser associated with travel (does your company give you Presidents' Day?).

Full disclosure: I am not a career coach, nor have I ever worked in human resources, so my thoughts on this are based entirely on my own opinions. This might not be feasible for everyone, but since travel is so important to me, I heavily consider a company's vacation and holiday policy when making a career change. For me, the amount of paid time off provided could make or break my decision to accept an offer, and I've occasionally asked for more. Some companies offer the opportunity to earn more days off the longer you work there, which is another thing to keep in mind.

I actively pursue career opportunities that offer more flexibility, like unlimited sick days or the ability to leave early for a doctor's appointment if I make up the time. That way, I can use my vacation days for vacation instead of for just being a human. I also work in an industry where  it's common to provide the week between Christmas and New Years' Day as holiday, which nicely maximizes my time.

If you're really strapped for time, consider negotiating unpaid leave. Obviously this is a trade off because in addition to the cost of your trip, you will need to consider the difference this makes in your salary. However, for some people, this could be a viable option. 

Remember when your co-worker told you about that sleepy little beach town on the coast of Lake Michigan that had surprisingly good restaurants and plenty of bars for hopping? And oh, by the way, it was just a short two-hour Amtrak ride from Chicago and just a five minute walk to the sweet little cottage she found on Airbnb, which happened to also be just a ten minute jaunt to the beach? And it was totally doable to just leave late Friday and come back late Sunday? Yeah, get your train ticket. Stat. 

Seriously, though, it pays to do a little bit of research into your greater surrounding area. If you have a car, anything within a 4 hour drive should be possible to accomplish in a weekend. If a set of wheels aren't your style, a lot of major cities have buses or trains you can take. For example, from Chicago, I can get to several small towns like Lake Geneva, Wisconsin, or Saugatuk, Michigan, that are known to play weekend host to city-folk. 

Who doesn't love a solid stay-cation every now and then? Whether on paper or just stored loosely in your noggin, I bet you have a hometown bucket list of sorts. Make it official and start crossing items off. Or, make a weekend out of it complete with a bonafide itinerary and travel companions (read: friends to drag along). Best part? The accommodation is free! 

Except not really. Because rent and stuff. Shrug emoji.

Not my favorite option, but still one to consider. I once booked a flight to D.C. only 12 hours before it was scheduled to depart so I could spend the weekend wandering our nation's capitol. Flights back to Chicago on Sunday were less-than-ideal and would have eaten into my totally thought-out (read: not at all) plans. So, I booked the 5AM flight on Monday morning instead, and I headed straight to the office after I landed. Not a bad deal.

You could also apply this thinking to overnight flights if you're skilled at sleeping on planes. Just grab a glass of vino, some earplugs and the best neck pillow on the planet, and next thing you know, you'll wake up in a new city.

Does your job require you to travel for work? Mine does! I've snuck in quick trips to NYC, Portland and San Francisco thanks to business travel. If your company has a flexible policy for booking work-related travel, consider asking to book your flight so that you can spend time in the city before your work begins. Bonus points if you can save your company some cash by finding a cheaper flight, too!

Did you know that every time a vacation day goes untaken, somewhere in the world a little kitten* dies? Just kidding! The cats are safe! But it does rip out a little piece of my soul, leaving me with a black, cold heart. Please don't leave me with a black, cold heart, people. Take those vacation days! Stick them on the ends of your weekends. Use them to lengthen a holiday. Or better yet, plan out the most bomb-ass trip of your dreams and fly away, pretty bird! Just make sure that at the end of the year, all of your time off has been exchanged for all kinds of memories.

*No kittens were harmed in the making of this post.

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  1. Great tips and ones I took full advantage of while working corporate. Especially the last one. I want to kill people who think they are being some kind of work martyr by not taking vacation - drives me crazy!

    1. Agreed so many times, Andi! I work for my vacation days. :)

  2. The way I do it is...why do I need to be in this office again? Look, boss. The overhead for my being here is insane. The carbon footprint from me having to drive here. The energy needed to keep my cubicle lit up. Crazy right? So can I just, like, work at home remotely? Seems to work!

  3. I worked in corporate America for two years and was able to do a 3.5 week backpacking trip through 5 countries in Asia by using my full 14 days of PTO the last week of December, merging that with Christmas being off, and adding another week from the new year's PTO reserve in January! Great advice and ideas though!! Now I'm a teacher, and I have a lot of time to travel- but unfortunately only during high season :/

    1. Wow that was a crafty trip! I love how you combined your PTO with the holiday break, but that must have made for a LONG year waiting for that trip to come! That's great that you have a gig that enables you to travel now.

  4. I worked in corporate America for two years and was able to do a 3.5 week backpacking trip through 5 countries in Asia by using my full 14 days of PTO the last week of December, merging that with Christmas being off, and adding another week from the new year's PTO reserve in January! Great advice and ideas though!! Now I'm a teacher, and I have a lot of time to travel- but unfortunately only during high season :/

  5. We do the same thing in Florida with weekend trips, playing tourist in our home town (we live in tourist central so that helps) and making the most of extended road trips to MI with stops along the way. Great list of tips.

    1. That's so smart! I love playing tourist in my hometown. I always learn something new... and I still get to sleep in my own bed!

  6. Great post! I have to say I haven't done well this year with planning ahead and so I haven't really done much travelling this year so far. Definitely need to remember to be more prepared. I'm a big fan of the red eye - I remember rocking up to lectures at uni with my suitcase!