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Probably Out of Office

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  • Charleston SC Travel Guide: Where to Eat, Stay & Explore

    Charleston SC Travel Guide: Where to Eat, Stay & Explore

  • 7 Day Maui Itinerary: The Perfect Honeymoon Trip

    7 Day Maui Itinerary: The Perfect Honeymoon Trip

  • Andaz Maui Review – Our Stay at the Andaz Maui at Wailea Resort

    Andaz Maui Review – Our Stay at the Andaz Maui at Wailea Resort

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    Airbnbs Asheville NC – Top 8 Stays for Couples & Groups

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    The Ultimate Guide to the Perfect Weekend in Asheville, NC

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    Best Honeymoon Hotels in Maui

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@probablyoutofoffice

24hrs in Lisbon 🚃 We had the best time exploring 24hrs in Lisbon 🚃 We had the best time exploring this city (full itinerary coming soon !!) Also lmk if you want a copy of my Google My Map with all the pins for my favorite restaurants, shops, hotels, bars, and more!! So sad our travel troubles cut our time in this city short BUTTTT we will for sure be back ❤️ #lisbonportugal #portugaltravel #travelgirldiary #eurosummer #lisbon
We’re 51 flights and 5 countries into 2026 with no We’re 51 flights and 5 countries into 2026 with no signs of slowing down any time soon!! If you’re busy working a full time job but love to travel, you’re in the right place because we take our PTO veryyyy seriously over here at @probablyoutofoffice ✈️ #adventurecouple #travelcouple #coupletravels #travelhumor #dinks
let’s go to Portugal !!! You guys I am seriously let’s go to Portugal !!! You guys I am seriously so excited for this trip!! The last few months have definitely been slower for me in the travel month so there is nothing like getting back into the swing of things with a 2 week trip to Europe!!! We’re going to Lagos -> Comporta -> Lagos -> Porto -> Douro Valley 🇵🇹🌴🍷⛵️ Stay tuned because you know I’ll be sharing all the recs soon 🫡 #portugal #portugaltravel #travelvlog #outofoffice #europeansummer
As someone with a severe travel addiction, these a As someone with a severe travel addiction, these are the 7 PTO strategies that I swear by None of them are complicated… and they’re all designed to help you save either TIME or MONEY to maximize your out of office days I wrote a full article for @thepointsguy Substack with all the details! You can comment “PTO” and I’ll send you the link to the post 🤗 . . . . . . . #outofoffice #travelmore #corporategirl #pto #travelgirldiary
One thing about me is that I WILL be using all of One thing about me is that I WILL be using all of my PTO!!! If you love to travel but are busy working a full time job, WELCOME TO THE CLUB ✈️🪩🌴🍸 I’m Madison 👋🏼 aka @probablyoutofoffice And I’m on a mission to help my fellow corporate girlies 👩🏻‍💻 travel more while working 9-5!! So if you also suffer from a severe travel addiction, let’s be friends 🫶🏼 #travelgirls #travelgirldiary #outofoffice #travelmore #travel
By popular demand, I’m sharing our Q4 2026 PTO gam By popular demand, I’m sharing our Q4 2026 PTO game plan a little bit earlier to help you with planning! Comment “Q4” for a link to the full breakdown on Substack 🫶🏼 For each month, I’m sharing my top picks & recs for: - a US weekend getaway - a national park trip - an international destination OCTOBER
🍂 Asheville
🏔️ Acadia National Park
🇱🇨 St. Lucia NOVEMBER
🗽 New York City
🏝️ Virgin Islands National Park 
🇲🇽 Mexico City DECEMBER
🌺 Maui & Haleakala National Park
🎄 Christmas Markets (Vienna, Strasbourg, Salzburg, Prague, Budapest) Don’t miss the PTO cheat sheet on the last slide so you can see exactly how to stretch your days this quarter! . . . . . . #traveltips #wheretotravel #ptohacks #corporategirlie #travelgirldiary
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Madison

About

Hi, I’m Madison — founder of Probably Out of Office. I help corporate women travel more on limited PTO, with researched itineraries, honest reviews, and points-funded stays.

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© 2026 Probably Out of Office
  • About
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    • LTK
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