There was a time in my early career when I’d scroll through Instagram and feel a pang of envy. Digital nomads were posting photos from cafes in Chiang Mai or lounging on the beaches of Bali, while I was reheating last night’s pasta in a dull office microwave. I assumed travel like that was only possible if you quit your job or went fully remote. It felt completely out of reach with a 9–5 schedule and just two weeks of annual leave.
But over time, I started experimenting squeezing in trips over long weekends, saying yes to work travel, and getting creative with PTO. Slowly but surely, I began to see how travel could fit into my life, not sit outside of it. It wasn’t always glamorous, and sometimes it meant red-eye flights or early Monday morning meetings, but it was worth it.
If you’ve been wondering how to explore more without walking away from your job or burning out, this post is for you. I’m sharing the real strategies that helped me go from one trip a year to several without sacrificing my paycheck or professional growth.
Use Your Paid Time Off Like a Travel Planner
Treating my PTO like gold changed everything. I used to take days off reactively sick days, mental health days, random Fridays when I felt burned out. But once I started thinking of PTO as a way to strategically create trips, things shifted. Now, I sit down at the beginning of the year with a calendar, my company’s holiday list, and a few trip ideas in mind.
If there’s a public holiday on a Monday, I might take the previous Thursday and Friday off to create a five-day adventure. Or I’ll use just two days to turn a regular weekend into a full week abroad. One of my favorite travel wins was when I used three PTO days around a national holiday and squeezed in a 9-day Portugal trip with enough time for Lisbon, Porto, and a coastal detour.
It also helps to plan early not just for better prices but because having a trip booked gives you something to look forward to. It’s like a light at the end of the work tunnel.
Stack Trips Around Long Weekends
Long weekends are my secret weapon. I used to treat them as time to rest at home, but once I started stacking travel around them, everything changed. The trick is being ready to leave either Thursday night or Friday early morning, and not minding a late Sunday night return. Sure, it can be a little exhausting but it’s a small price to pay for waking up in a new city or country.
I’ve flown to Denver for a hiking weekend, spent Easter in Mexico City, and even managed to see Reykjavík and the Blue Lagoon in Iceland over a long weekend. If you can handle a little jet lag and plan your itinerary wisely, you’d be surprised how much ground you can cover in 72 hours.
It’s not about doing everything; it’s about making the most of the time you do have.
Try Bleisure Travel (Work + Play)
Work trips used to feel like missed opportunities until I realized I could turn them into mini-adventures. Now, if I have a conference or client meeting in a different city, I tack on a night or two. One Friday meeting in New York turned into a weekend of museums, bagels, and Central Park strolls.
It’s not just about exploring sometimes the best part is the mindset shift. You’re already in travel mode, so extending your trip feels seamless. Check with your company’s travel team or manager some are totally okay with shifting return flights as long as you cover the cost difference (and sometimes there isn’t one).
Even a simple staycation in a new part of the same city can feel like bleisure if you extend the vibe a bit.
Plan Local Getaways and Day Trips
There’s something magical about spontaneous road trips. I used to think travel meant hopping on a plane, but then I discovered the charm of nearby towns, offbeat hikes, and cozy B&Bs just a short drive away. Some of my favorite weekends have been the ones where I packed a bag, picked a spot within two hours, and hit the road.
One weekend I drove out to a nearby vineyard town I’d never heard of. Another time, I booked a last-minute cabin in the woods. No pressure to see big sights or tick off tourist checklists just rest, nature, and maybe a local cafe or two.
If I’m feeling stuck but don’t have the energy for a big trip, these micro-adventures do the trick. And the best part? They’re budget-friendly and require almost zero prep.
Embrace Remote Work Days (When You Can)
If your job allows for remote work, even occasionally, it’s worth exploring how to make it part of your travel rhythm. I’m not saying you need to be a full-time digital nomad (though hats off if that’s your path!), but even one remote day here and there can stretch your weekend trip into something more substantial.
I’ve worked from all kinds of places: mountain cabins with strong coffee and slow mornings, cafes in Montreal with fresh croissants, and once, from a rooftop Airbnb in Tulum with surprisingly great Wi-Fi. These weren’t full-on vacations just soft landings that helped me ease back into work mode without cutting my trip short.
Of course, you need to be realistic about time zones and your workload. But if you’ve got a quiet Monday ahead, why not work from that charming Airbnb one more day and head back Tuesday instead?
Use Your Vacation Days for Rest and Fun
I used to feel weird about taking vacation days unless it was for a big international trip. But the truth is, rest doesn’t always mean two weeks in Europe. Sometimes it’s a cabin in the woods with no Wi-Fi, a day at a thermal spa, or just three days to do nothing in a new city.
I’ve started using my PTO for exactly what I need whether that’s adventure or recovery. I’ve taken a solo trip to a wellness resort when I was burned out, and I’ve booked last-minute flights to visit a friend across the country when I needed a change of scenery.
Vacation days are there for you. You earned them. Don’t hoard them like gold you can’t take them with you, and you might just come back from your time off with a fresh perspective (and some killer travel stories).
Keep a “Weekend Trip” Bucket List
This is one of my favorite hacks. I keep a note on my phone with a running list of places I want to visit that are perfect for 2–3 day trips. That way, when I see a good flight deal or a long weekend is coming up, I don’t waste time trying to figure out where to go I already have ideas lined up.
The list includes everything from nearby national parks to cities a few hours away by flight. It’s super casual just names, maybe one or two notes. Things like “Santa Fe – art markets” or “Asheville – fall foliage.”
It makes trip planning way less stressful and gives me something to daydream about when I need a little spark of excitement midweek.
Travel During Off-Peak Seasons
This one’s a biggie. I used to travel during summer and December holidays like everyone else until I realized how much money (and sanity) I could save by going off-season.
Take my trip to Florence, for example. I went in late October. It was still warm enough to eat gelato outside, but there were no crowds. I walked right into museums and had quiet morning strolls through the city center without elbowing through tour groups. Hotels were cheaper too like half the price.
Shoulder seasons (April–May and September–October) are perfect. You get better deals, nicer weather, and fewer tourists. It’s a win-win-win.
Maximize Travel Credit Cards and Airline Miles
I used to ignore all the points and miles stuff because it seemed complicated. But once I got a travel rewards card and actually paid attention to my points, things got real.
I picked a card with no foreign transaction fees and good bonuses for travel spending. Now I earn points on groceries, bills, and flights and I’ve already used them for roundtrip tickets to Mexico and a couple of free hotel nights.
It’s not about chasing every promo. Just find one or two cards that fit your lifestyle, pay them off each month, and let the points build. It’s like giving yourself a little travel bonus with every purchase.
Say Yes to Spontaneity (Sometimes)
Some of my best travel memories weren’t planned. A random road trip. A surprise concert in another city. A friend texting, “Want to drive to the coast this weekend?”
Saying yes can feel chaotic at first, especially if you’re someone who loves a plan (hi, it’s me). But those unplanned adventures? They often turn into stories you’ll tell for years.
So if your calendar’s clear and your heart says go, listen. You can always figure out the details later. Not every trip has to be perfect. Sometimes, it just has to happen.
Final Thoughts
You don’t have to quit your job or wait for the perfect moment to start traveling more. With a little planning (and some clever calendar math), it’s absolutely possible to make travel a bigger part of your life.
It might mean some early flights or Monday mornings with tired eyes, but it also means waking up in a new place, trying new food, and collecting experiences you’ll never regret.
