As far as I can tell, I’ve had 17 consecutive days off on two different occasions. The one I mentioned earlier, bolstered by weekends and Memorial Day, and once two years ago when I moved across the country (but stayed in the same job, as I was able to transfer offices).
17 Days for my Honeymoon, since then the great length was last year 13.
More than 30 days. But my company gave us sabbaticals, so that was a one-shot deal for me. I wasn’t there quite long enough for the second one. Aside from that, it would have been 2 weeks. I got 4 weeks of vacation per year, but didn’t ever take it all at once. No one prevented me from doing that; it was my preference.
Oops. We’re not supposed to count sabbaticals. So make that 2 weeks.
“I’m not trying to measure the most days of paid (or unpaid) leave taken, just the overall duration of the trip.”
In your case, 16 days.
23 days in the Land of Smiles!
Two weeks if we are talking about the trip. I’ve spent that much time in the Outer Banks every summer for the last 10 or 12 years. Previously, it was only one week.
If we are talking leave time, I was a teacher. So I had 10 weeks leave every Summer along with the Holidays and other days off scattered through the school year.
My longest was about two months, but I am self employed and it was unpaid more or less.
I took a 3-week vacation once, back in 1982, when I was a paralegal. That was a more vacation-friendly era, and my then-occupation tells you they could do without me for that long. But even so, taking that much time off at once did raise some eyebrows.
17 days. In 2015. I’ve only had one other full 2 week vacation in my working career, in 2014. I usually can take 2 or 3 week-long trips per year, but have made time off a higher priority in my career than maximizing pay, and am very sad that American culture doesn’t value time off like most other Western cultures.
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Speaking for all teachers here - we win. Unless you count any day with any work done a work day, even if you don’t get paid. Then we lose.
In 19 years of working full time, I’ve never taken more than 5 consecutive days of work off. If you include weekends, I’ve been gone for a full week.
I was confused by the wording, so I voted 5 or less because I’ve never taken a trip longer than 5 days.
But then I saw post #11 and it would seem that it would have been better if I counted the 10 days off from work I take for Christmas + New Year. I just don’t happen to go anywhere.
So I dunno. I am a small business owner so I can’t afford to take trips, or take time off 
As a public servant, I get 5 weeks/year. Theoretically, I could request all five weeks at once but most I’ve ever done has been 2½.
Last year I ended up not spending my vacation days until the very end of the year … then when I added it all up plus the time we get for Christmas/New Years holidays, I was able to take the back half of December off - 18 days (Dec 16-Jan 2). It was glorious, though I didn’t really go anywhere.
Do you mean a vacation in terms of a trip somewhere, or just the longest span of days we’ve taken off from work using “vacation time”?
I think I’ve taken two weeks only one time ever, but the trip out of town part was only a portion of that.
Whoops, in the last five years, no. That was for my fortieth birthday, > 5 years ago.
When I took my sabbatical, I knew I was fully in sabbatical mode when I had trouble remembering some of the names of the engineers who reported to me. 
The night before I was to get on a plane for “places far and wide”, the guy who was to sit in for me while I was gone called me, as he had some papers he needed me to sign. He then asked if I wanted to know about some “serious shit that was going down”. I just said no, since there would have been nothing I could do about it, and it would all probably blow over by the time I got back. Which it did.
But, wait. Shouldn’t it be “or fewer”?
Hey! Ouch.
(I don’t care. I’m not one of those “10 items or fewer” pedants, just mocking them.)
As for the OP, I’ve only worked maybe three years for someone other than myself. The longest vacation I took at that time was a two week vacation, but it was a mandatory one (and I was working in a company in Europe, where I got five weeks per year.) On my own, as for like a real, leave-the-house vacation, I went to India for three weeks a few years ago, but there was about five days of work included in there, so it was kind of a work-play vacation.
128 days!
Woo!
In the last five years, four or five days. I once took 30 when I was in the Navy.
I did a 26-day cruise with my mom 3 years ago. I don’t know if it counts because I was between jobs. I’d quit one and it wasn’t till a year later that I got another.
I retired 6 years ago, but I’ve had 3 temp and 2 real jobs since then, because retirement was boring.
Back when I was working, I don’t think I ever had 2 weeks in a row.