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@probablyoutofoffice

Corporate work travel is all fun and games until y Corporate work travel is all fun and games until you’re three weeks behind on laundry and can’t remember the last time you slept in your own bed 🙃 I honestly don’t mind traveling for work, but I swear it either comes in waves where I’m living out of a suitcase orrrr I don’t have a single trip on my calendar for months. There’s no in between lol And while I will absolutely never complain about the airline miles, hotel points, or someone else picking up the tab for dinner, I think the hardest part is trying to maintain some semblance of a normal routine Especially when you’re also trying create content and your evenings are spent at work dinners instead of editing the 847 videos sitting in your camera roll Buttttt I do love that this career has given me the opportunity to travel as much as I do, both on and off the clock!! If you’re new here, hiiii 👋🏼 welcome to @probablyoutofoffice, where we’re on a mission to travel as much as humanely possible without putting our careers on hold! If that sounds like you, stay tuned for more for PTO hacks, obsessively researched itineraries, and honest travel recommendations 🫶 #corporategirl #worktravel #corporatelife #PTO #travelcontentcreator
Every year, Michelin comes out with their official Every year, Michelin comes out with their official Key rankings for hotels (the same way they give stars to restaurants) AND these are the places I’ve visited that made the ranking in 2026! Also, in case you’re wondering what the Keys even mean… here’s a little cheat sheet: 🔑 One Key = A very special stay. A true gem with personality and great service that goes above and beyond its price range. 🔑🔑 Two Keys = An exceptional stay. A unique, character-filled hotel run with considerable care, charm, and a guarantee of a memorable experience. 🔑🔑🔑 Three Keys = An extraordinary stay. The absolute pinnacle of comfort, service, style, and design—representing a destination in its own right for a trip of a lifetime *Being listed in the Michelin Guide isn’t the same as holding a Key, the Keys are the actual award* My official ranking of every MICHELIN Key hotel I’ve stayed at (so far), from least to most favorite No. 7 → No. 1: 7. Palacio Ludovice — Lisbon, Portugal · One Key 6. Madeline Hotel — Telluride, CO · One Key 5. Sugar Beach — St. Lucia · One Key 4. Sublime Comporta — Comporta, Portugal · One Key 3. Four Seasons Anguilla — Anguilla · Two Keys 2. Rosewood Mayakoba — Playa del Carmen, Mexico · Two Keys 1. Six Senses Douro Valley — Douro Valley, Portugal · Two Keys 📌 SAVE this for your next splurge & tell me which one you’re booking first??? #michelinguide #luxuryhotels #hotelrecommendations #travelitinerary #luxurytravel
I’m a firm believer that you don’t have to quit yo I’m a firm believer that you don’t have to quit your 9–5 to travel the world ✈️ To be honest, having a corporate job is what has made it possible for me to travel MORE and BETTER You just have to be a little strategic about how you use your PTO, where you spend your money, and how you take advantage of credit card points & miles And as someone who spends an ungodly amount of time researching hotels, destinations, flights, and itineraries, I started @probablyoutofoffice as a way to share all of that with you and connect with other women who share my love of travel! So if you’re a fellow corporate girl who wants to maximize her vacation days, find affordable luxury hotels, travel smarter with points & miles, and take trips that are actually worth your hard-earned PTO… Consider this my formal application to be your travel obsessed bestie 🥂 #traveltips #travelgirls #pointsandmiles #travelplanning #corporategirl
unfortunately, my dream job is being on vacation 🤏 unfortunately, my dream job is being on vacation 🤏🏼 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!! #travelgirls #corporategirl #outofoffice #sidehustle #relatable
accurate representation of my husband’s vacation v accurate representation of my husband’s vacation vs mine 🤌🏼 #husbandandwife #relatable #travelhumor #travelcouple #europetravel
Comment PORTUGAL for my custom Google Map + our fu Comment PORTUGAL for my custom Google Map + our full 2-week Portugal itinerary with all the hotels, restaurants, and spots we loved! We spent two weeks exploring Portugal and WOW… this trip exceeded my expectations in pretty much every way. And thanks to Labor Day, we were able to take this 13 day trip with only 8 days of PTO! You guys know I’m usually the queen of a jam-packed itinerary, but having two full weeks meant we could actually slow down and enjoy each destination without feeling like we were constantly on the move. Here’s a quick overview of our itinerary: 📍Lisbon: Easily one of my favorite European cities! We spent most of our time wandering different neighborhoods, shopping, eating, and finding cute spots for a glass of wine. 📍Comporta: Probably the biggest surprise of the trip! Think northern coastal California meets a boho European beach town. We stayed at Sublime Comporta, which I absolutely loved, and spent a full day at their beach club. 📍Lagos / Algarve: I was worried Lagos would feel too touristy (and it definitely was in parts), but the coastline is SO beautiful. Our private boat day exploring the Algarve coast was one of the highlights of the trip. 📍Porto: Two nights felt like the perfect amount of time here. We explored both sides of the river, did some shopping, and of course had to try the famous port wine. 📍Douro Valley: We definitely saved the best for last. Six Senses Douro Valley is so special, and the wine experiences here were incredible. If there’s one place I’d tell you to splurge on this itinerary, it’s this one. Portugal has SO much more to offer than just Lisbon and Porto, and I’m really glad we made the effort to explore beyond the major cities. I shared our entire itinerary over on Substack — where we stayed, what we did, where we ate, how we got between destinations, and what I would (and wouldn’t) do again. PLUS: my custom Google My Map with every place I researched and personally vetted, so you don’t have to start planning from scratch. 📌 SAVE this post for your Portugal trip & comment PORTUGAL for the link 🔗 #PortugalItinerary #PortugalTravel #VisitPortugal #DouroValley #LisbonPortugal
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Madison

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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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