Hi, I’m Madison! The founder of The Out of Office Edit & @probablyoutofoffice. As someone with a regular 9-to-5 and a severe travel addiction, one of the number one questions I get asked is, “How do you travel so much with a full-time job?”
And the real answer is kind of boring. I don’t have unlimited PTO or a trust fund … I’m just obsessive about squeezing every possible day off out of my calendar. So here are the top seven strategies I use to stretch my time off (and my paychecks) as far as possible for travel.
Before every trip, I built out what I like to call a “Travel Menu.” This is NOT an itinerary. It’s basically a curated list of restaurants, activities, neighborhoods or anything else that catches my eye during planning. I organize all of these recommendations in one place, so I have vetted options to pick from once I’m actually on my trip.
I love this because it gives you the freedom not to be chained to a rigid schedule, but it also gives you the peace of mind that you won’t end up without a plan because you haven’t done any research.
The last thing you want to be doing is standing on a street corner in Paris, starving after a day of exploring and panic-Googling “best restaurants near me.”
And the best part is that all of this lives in a Google My Maps, which brings me to number two …
This is where your “Travel Menu” actually lives. Ahead of every trip, I create a custom Google My Map for the destination. You’re able to add unique pins that you can color-code and categorize for every hotel, restaurant, cocktail bar, neighborhood, boutique or anything else you like from your research. And then I download the map offline, so I don’t rely on Wi-Fi to plan my day when I’m on the go.
It’s obviously a little more work upfront, but it makes the trip so much more enjoyable when you’re actually on the ground because it’s so easy to logistically plan out your day or even pull up the map while you’re out and see which spots you’re near.
Most people take long weekends from Thursday to Sunday or Friday to Monday. I started flipping it and will actually fly out Saturday morning, come back Tuesday evening, and then take Monday and Tuesday off instead.
I love this for a few reasons:
Sunday and Monday nightly rates are almost always lower than Friday and Saturday.
You’re traveling when everyone else is at work, so you’re almost guaranteed to have fewer crowds.
You’re not trying to cram a full work week into four days and then stress-packing at 9 p.m. Thursday (guilty as charged). You get Friday after work to pack, so you can actually get a full night’s sleep and not start your trip on a miserable note.
Federal holidays are free days off, and the PTO math can be really good when you plan your trips around them.
For example, this year, Christmas and New Year’s Day are on a Friday, which means four PTO days (12/28-12/31) could get you a 10-day vacation!
At the start of the year, I go through my calendar and mark off every corporate holiday I get and use that as a framework for when to plan my trips — especially the big bucket list ones that require 7+ days.
Peak season is overpriced, overcrowded and destined to have you spending half your trip waiting in lines or fighting for dinner reservations. Shoulder season (the few weeks to a month right before or after peak) gives you basically the same experience for a fraction of the cost.
I’m talking November in the Caribbean before holiday pricing kicks in, or late September in Europe, when the weather is still beautiful but the summer tourists have cleared out. It’s the same destination, mostly the same weather and way less competition for everything.
I have expensive tastes in travel, and a normal corporate salary, so points and miles are my strategy for closing that gap. In my mind, points and miles can do one of two things — either they enhance the experience in ways I’d never pay cash for, or they save me money that I can redirect to other parts of the trip.
For example, I’ve flown Emirates’ A380 in one of the best business classes in the sky, which I would never pay for out of pocket. But using points to get there? Not, I’m starting my vacation at a bar on a double-decker plane, instead of being crammed in a middle seat for 7+ hours.
On the savings front, we booked the Andaz Maui with Hyatt points, which freed up money that would otherwise have gone to the hotel for better restaurants, a sunrise snorkel excursion and maybe a new vacation outfit or two …
At the beginning of the year, I pick one, maybe two, must-do trips. These are the nonnegotiable ones, but everything else I end up booking is based on whatever deals I find.
Telluride is the perfect example. We hadn’t planned any travel for the ski season at the beginning of the year, but after I found exceptionally cheap flights to Telluride, we built a trip around those flights and had the most amazing time.
Some of our favorite travel memories have come from destinations that were never part of the original plan.
You don’t need more PTO (although, let’s be honest, that would be great!), you probably just need a better plan for how to use the days you already have.
If you liked this post, I share a lot more on my Substack — destination guides, PTO tips, hotel recommendations and my hot takes on what’s actually worth your time and money when it comes to travel.
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And don’t miss TPG’s piece on my Substack today covering the best award flight redemptions to stretch your points even further!
— Madison
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