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✈️ detailed itineraries, destination guides, travel tips
🫶🏼 helping you maximize your pto
📍 charlotte, nc
💌 madison@probablyoutofoffice.com

Part 2: 🗓️ WHEN to plan your road trip to Jac

Part 2: 🗓️ WHEN to plan your road trip to Jackson Hole, Grand Teton, Yellowstone & Bozeman 🚗

Today we’re breaking down when to go and more importantly how to MAXIMIZE YOUR PTO‼️

[📌 SAVE this guide for planning]

For this 7-day road trip itinerary you only need 4 days of PTO 🙌 
Here’s some pros and cons for deciding when to go 👇

🇺🇸 Memorial Day (this is when we went last year!) ✔️ Early wildflowers ✔️ Fewer crowds ✖️ Some roads may still be closed. Roads are typically reopened by the last week of May, but this can vary depending on weather!

☀️ Juneteenth ✔️ Perfect weather ✔️ Waterfalls at peak flow ✖️ Snow may linger on high trails

🎆 4th of July ✔️ Peak summer adventure ✔️ All roads + hikes open ✖️ Biggest crowds + $$$

🍂 Labor Day ✔️ Cooler weather  ✔️ Tourists are dying down as schools go back ✖️ Shoulder season weather can be unpredictable

Follow @probablyoutofoffice ✈️ for more tips on planning your Grand Teton & Yellowstone National Park itinerary✨ — I’m covering where to stay, what to do, and the full itinerary next!
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#jacksonhole #grandteton #yellowstonenationalpark #bozeman #usaroadtrip #adventurecouple #usanationalparks #summertravel #bucketlistadventure

🚨 New Series Alert 🚨 Bucket List Road Trip

🚨 New Series Alert 🚨

Bucket List Road Trip 🚗
📍 Jackson Hole, WY
📍 Grand Teton National Park
📍 Yellowstone National park
📍 Bozeman, MT

Last year, we did this exact trip with my whole family 🫶🏼 and it was honestly my favorite trip we took all year (and we traveled ✈️ A LOT last year).

I’m fully convinced this a road trip that everyone needs to do at least once in their lifetime‼️ so I’m breaking down everything you need to know to plan your trip 💻 in this new series.

So, what can you expect?

I’ll share all of the details you need to plan your trip 👇🏼
⭐️ When to go?
⭐️ Where to stay?
⭐️ What to do?
⭐️ Costs?
⭐️ How to maximize your PTO?

And more tips and tricks✨ along the way!

Drop any questions you have in the comments 💬 and I’ll be sure to answer them throughout this series!
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#travelbucketlist #travelinspo #2025travel #travelcouple #grandtetonnationalpark #yellowstonenationalpark #usaroadtrip #usanationalparks #visitwyoming #visitmontana

This new tool is a GAME CHANGER for planning a tro

My #1 tip for finding business class flight deals

My #1 tip for finding business class flight deals 👇🏼

Thrifty Traveler Premium ✈️

📲 Want to try it for yourself?
 Comment “flights” below and I’ll DM you a link for $10 off your first year 🙌🏼

This is by far the best flight deal subscription ✨ I pay for — and it’s worth every penny.

Thanks to @thriftytraveler we’ve been able to:
🥂 Fly Emirates business class to Italy using points in 2024!  🌎 Book two more business class flights on Emirates & Lufthansa for 2025 — all thanks to points and miles alerts’  🔔 Discover award availability that I NEVER would’ve found on my own (seriously, the text and email alerts are amazing‼️)

💸 Whether you’re sitting on Amex points, Chase points, or airline miles… this subscription helps you maximize the value of your points by alerting you to the best redemptions as soon as they become available 🚨 because they never last long!
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#pointsandmiles #awardtravel #flightdeals #travelmore #traveltipsandtricks #businessclass #traveldeals #emiratesbusinessclass

In 2024, my husband and I managed to take 58 fligh

In 2024, my husband and I managed to take 58 flights, visit 6 countries, explore 3 national parks, and more ✈️ all while working full time jobs with limited PTO and my goal is to help you 🫵🏼 do the same!!

So if you’re busy working a full time job 💻 but want to learn how you can save time ⏳and money 💸 to prioritize travel in your 20s & 30s you’re in the right place!

@probablyoutofoffice is your one stop shop ✨ for detailed itineraries, weekend getaways, and travel tips that will help you get out of office more ✈️🌎

If that sounds like you, let’s be friends 🫶🏼
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#adventurecouple #travelcouple #coupletravels #travelhumor #dinks #traveldinks

3 Perfect U.S. Destinations for a Long Weekend Get

3 Perfect U.S. Destinations for a Long Weekend Getaway This Spring 🇺🇸✈️

Planning your next trip but don’t have a lot of PTO? These destinations are perfect for a long weekend escape ☀️ whether you’re craving adventure, charm, or tropical vibes!

[📌 Save this post for later and share it with your travel buddy!]

📍 Sedona, Arizona – Red Rocks & Relaxation 🏜 ⭐️ Where to Stay: Enchantment Resort, Amara Resort
🥾Things to Do: Hike Devil’s Bridge, Cathedral Rock, or Bell Rock, take a Pink Jeep Tour, explore Tlaquepaque Arts Village 🍽️ Where to Eat: Mariposa (stunning views), Elote Café (Mexican must-try)

📍 Charleston, South Carolina – Southern Charm & Coastal Beauty ⛲️ ⭐️ Where to Stay: The Ryder Hotel, Hotel Emeline  🛍️ Things to Do: Stroll Rainbow Row, shop on King Street, relax on Sullivan’s Island 🍽 Where to Eat: Leon’s (fried chicken & oysters), Miller’s All Day (the BEST breakfast), Sorelle (modern spin on Italian)

📍 U.S. Virgin Islands – Tropical Escape, No Passport Needed! 🏝 ⭐️ Where to Stay: The Ritz-Carlton St. Thomas 🤿 Things to Do: Snorkel at Trunk Bay, beach hop on St. John, sail to the British Virgin Islands, visit Magen’s Bay Beach 🍽 Where to Eat: The Easterly (coastal cuisine), Caribbean Fish Market (local seafood)
 Follow @probablyoutofoffice for more travel tips & itineraries ✨✈️
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#weekendgetaway #itinerary #travelguides #travelgirls #springbreak #charlestonsc #sedonaarizona #stthomasvirginislands #usvirginislands #weekendtravel

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