Madison is the founder of Probably Out of Office, a travel and lifestyle brand curated for corporate women who want to travel more without quitting their 9-to-5.
She creates obsessively researched itineraries, honest reviews, and PTO strategies designed to help you get the most out of your limited time off — because when you’re working with a real schedule and a real budget, every trip needs to count.
She started Probably Out of Office after one too many trips planned off other people’s recommendations didn’t live up to the hype. The overrated restaurant with the two-hour wait. The “must-see” viewpoint that wasn’t worth the detour. The trendy hotel that looked great in a reel and was underwhelming in person. She was tired of settling for mediocre vacations, so she started doing the research herself and sharing what she found.
And when Madison says research, she means it. She was building detailed itineraries planned down to the minute for her family’s Disney World vacations by the age of 12, so the obsessive planner is just who she is. Today that looks like reading the menu before she books the restaurant, building custom Google Maps, and thinking through all of the logistics that take a trip from good to great The result is itineraries and guides you can trust, with the hard decisions already made for you.
Think of her recommendations like a Travel Menu — pick what works for your trip, skip what doesn’t, and don’t spend your vacation trying to figure out what’s worth doing. She already did that part.
By day, Madison works a full-time corporate job. By nights, weekends, and every PTO day she is jetsetting around the world with her husband Will. She has traveled to 16 countries (and counting), and loves the challenge of making her expensive taste work on a corporate salary.
What You’ll Find Here
Luxury & Adventure Travel
One week it’s a sunset spritz at a luxury resort booked entirely on points. The next it’s a national park road trip with campfire dinners and sunrise hikes. Probably Out of Office covers both — because Madison believes the best travel bucket list includes a little bit of everything.
Detailed Itineraries, Curated Guides, and Honest Reviews
On this site you’ll find day-by-day itineraries with specific hotel, restaurant, and activity recommendations, plus honest reviews that include what’s worth it and what’s not. The places that need to be on your bucket list — from the cutest new boutique hotels for a weekend getaway to that once-in-a-lifetime European summer trip, and everything in between.
Every guide comes with the details that actually matter when you’re planning: where to stay, where to eat, what to skip, and how to structure your days so you’re not wasting time on the ground. Madison will tell you what’s overrated just as fast as she’ll tell you what’s worth the splurge — because if she only ever told you what was great, you wouldn’t be able to trust her when she told you something actually was.
Travel Tips
Madison and Will have flown business class around the world and booked 5-star hotels thanks to points and miles for a fraction of what it costs in cash. On the site you’ll find tips and strategies for traveling above your pay grade, PTO math for stretching your days off into real trips, packing guides, and custom Google Maps for every destination she covers. The goal is always the same: travel better without burning through your savings to do it.
Where to Find Madison
This site is where the deep research lives — the full itineraries, detailed reviews, and everything you’ll want to reference when you’re actually planning a trip.
For quicker destination guides and travel tips, follow her on Instagram @probablyoutofoffice and Tiktok @probablyoutofoffice.
And for the most honest, unfiltered version (the real opinions, the behind-the-scenes, and the things that don’t make it to the grid) subscribe to her newsletter, The Out of Office Edit.
