How to Maximize Vacation Days for 37+ Days of Travel

For the average worker, they’re given a set amount of vacation days to use during the year, in accordance with their company’s policy. Even with a set amount of days given, there are ways to maximize those vacation days to their fullest potential.

Make Long Weekends with Federal Holidays

If you add a vacation day to a Friday or Tuesday (assuming Monday is the Federal Holiday), you can end up with a 4-5 day vacation, simply by using 1-2 days of vacation time.

Take 4 Days Off to Make a 9 Day Vacation

If you have a Federal Holiday on a Monday, and take Tuesday through Friday off, you end up with a 9 day vacation for the “price” of taking 4 days off.


Here’s how I maximize my days:

I’ve created this schedule assuming one has 12 vacation days to use during the year.


Take Tuesday off after MLK Day, to create a 4 day weekend.

Total Vacation Time: 4 Days


Take Tuesday off after President’s Day, to create a 4 day weekend.

Total Vacation Time: 4 Days


Take Monday off after Easter, assuming you have Good Friday already off, to create a 4 day weekend.

Total Vacation Time: 4 Days


Take Tuesday through Friday off after Memorial Day to create a 9 day vacation.

Total Vacation Time: 9 Days


Take Tuesday off after Labor day to create a 4 day weekend.

Total Vacation Time: 4 Days


Take Monday through Wednesday off prior to Thanksgiving to create a 9 day vacation.

Total Vacation Time: 9 Days

Floating Day

Take one vacation day alongside a weekend or other holiday to create a minimum 3 day weekend, or 4 depending on the calendar and when holiday’s fall.

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Total Vacation Time: 3 Days

Total Vacation Time? 37 Days


Tips and Tricks

Take Evening Flights or Red-Eyes

If you leave on a Friday, find a flight after work, thus getting you into your destination that night, or at least a head-start to your destination. When returning, look into red-eye flights that get you back into work for the next day. For example, there is a red-eye LAX-IAD flight getting in at 6am the next day, with plenty of time to spare prior to needing to be at your workplace. There are similar options to JFK and other eastern cities.

Extend Your Business Trip

If you’re on a business trip, look into adding vacation time onto that trip. Perhaps the city you are in is interesting enough for some tourism time, or it gets you that much closer to your desired destination. Your company may be willing to help with a companion to take with you, or flights and hotels. I know one case where a company paid for a business traveler to stay 2 extra nights in a destination simply because the flight was dramatically cheaper leaving 2 days later than it was the day of, to return home.

Weekends and Holidays are Your Friends

If you already haven’t seen it in the examples I used above, weekends are your best friends when it comes to vacation time. Tacking on days on either side get you “free days.” DON’T take a vacation day in the middle of the week unless you absolutely have to.

Find Destinations That Work for Short Trips

Of course, many US destinations work for weekend or long weekend trips, but open up your boundaries a bit to see what’s possible. Europe is a great place to visit for a long weekend and because the flights tend to work in your time advantage, it can maximize your time to play tourist. Don’t land-lock yourself to driving a few hours down the road. Look at the options of what you can get done in a weekend and make it happen. There are many international cities where this is possible.

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  1. AndyTLe says

    Great strategies. I do the same to maximize my vacations.

    The redeyes are brutal though. Showering in the club and rolling into to work.

  2. Ima says

    Is there a way to find out where I can go for a short trip.
    For example – I decide today Tuesday to go somewhere for this weekend (at the moment I don’t care)
    I assume it’s worth $x for this simple weekend trip. (flight + hotel + rent a car + food for a total of 48hrs in that location)
    I would fly in & out of Y airport.
    I’m alway’s up for a trip but most all the travel sites I know of ask me where I want to go – and as I mentioned, I don’t care.
    And I get the least helpful suggestions when I post to any blogs, like: you really need to stay in location A for 10x the amount of time you are going to be there, why don’t you sit at home and ……

    In summary
    I’ll spend $x to go somewhere for a weekend trip. Once I have that data I will decide if it’s valuable enough to me to book it.

    Reason why I need this: A few years ago for Thanksgiving I had no plans. My work was off the entire week. I could make it into a 9day vacation. I spent day’s just picking places at random to find out where a good price would be, then checking another and another. It would have been amazing if I just said, I have $1,000 to spend on airfare and I need to depart from my local airport – now give me all my optional places.

  3. TonyM says

    We lived in London, England for 3 years. 8-10 bank holidays with 28 paid days off. It really stung when we moved back to the US.

  4. Ven says

    I prefer to use the X-Mas/New years time frame.

    1) In 2016 7 days off will get you potentially 16 days of vacation.
    2) Since everyone is off during this period, most work places slow down to a crawl so you won’t miss much. (assuming your not in retail ::))

  5. says

    What a great post. I love lots of long weekends to maximize my vacation time. If only I got some of those fluff holidays off of work!

  6. El Presidente says

    I’m really TICKED off right now. I have tons of vacation time, plenty for 5 weeks family Europe vacation. When you have little kids and are going to adjust that many time zones might as well stay a while. When I put in the request, my manager informed me of a new policy that no single vacation be more than 3 weeks. ARrrrrrgh!


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