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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

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
Sometimes a hotel is really just a place to sleep, Sometimes a hotel is really just a place to sleep, while others are the entire reason you visit a destination. And that difference is exactly how I decide where to save vs. splurge when traveling. As someone who works a full-time corporate job but is also admittedly obsessed with luxury hotels, I’ve learned that affordable luxury isn’t about traveling cheaply all the time. It’s about being intentional with where you spend your money. Enter: @sixsensesdourovalley This Two Michelin Key hotel in Portugal’s Douro Valley wine region had been on my bucket list for YEARS, and after finally spending two nights here, I can confidently say it lived up to the hype!! A few things that made this stay so special ↓ 🍇 The setting: A stunning property surrounded by rolling vineyards and overlooking the Douro Valley! 🍷 The wine experiences: From wine vending machines (yes, seriously) to an incredible guided tasting with the resort’s sommelier, this was a wine lover’s dream. 🧖‍♀️ The spa: Six Senses is known for its wellness experiences, and this property is the perfect place to slow down and recharge. 🍽️ The dining: Incredible food, local wines, and an emphasis on showcasing the region’s flavors. ✨ The experience: Unlike a city hotel where you’re out sightseeing all day, this is somewhere you’ll actually want to spend time enjoying everything the property has to offer. My personal philosophy is to save on hotels when the destination is what you’re there to explore. Splurge when the hotel IS the destination. And for me, Six Senses Douro Valley was 100% worth the splurge. 📌 SAVE this for your Portugal bucket list and FOLLOW @probablyoutofoffice for more honest luxury hotel reviews, travel guides, and tips for making the most of your PTO! . . . . . #SixSensesDouroValley #SixSenses #DouroValley #LuxuryHotels #PortugalTravel
so crazy how that works… #outofoffice #relatable so crazy how that works… #outofoffice #relatable #airport #travelgirls #airportlife
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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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