How to Plan a “Workation” That Doesn’t Burn You Out (or Your PTO)

Remember when “working from the beach” sounded like an impossible dream? Now it’s a real strategy. The workation—part remote office, part vacation—has become one of my favorite ways to travel. You get to change up your view, explore somewhere new, and still stay on top of your work without burning all your vacation days.

But let’s be honest: a poorly planned workation is just working in an unfamiliar, more expensive living room. I’ve learned that getting it right takes a bit of planning, but it’s so worth it when you wrap up your last call and step straight onto a hiking trail or into a buzzing new city.

Here’s what actually works.

Why Bother With a Workation?

It’s not just about getting away—it’s about getting inspired. Sometimes a new backdrop gives you that creative boost your home office just can’t. When you find the right balance, you get to be productive, see the world, and maybe even enjoy longer trips for less.

Why I love them:

New scenery means more energy and fresh ideas.
You can stretch remote work benefits without burning PTO.
Travel costs go down when you’re not rushing through a jam-packed week.
You end up feeling less like you “escaped” and more like you just…live differently for a while.

Step 1: Be Honest About Your Work Reality

Ask yourself:

Can you really get your work done remotely?
Do you have control over your schedule, or is it all meetings, all day?
Is your work flexible enough if the Wi-Fi cuts out for a minute?
Can you actually carve out time to explore?

If you’re glued to Zoom from dawn till dusk, a workation might just feel like working from a slightly nicer cell. But if you have real pockets of free time and don’t need perfect internet 24/7, you’re golden.

Step 2: Pick a Place That’s Ready for Remote Work

Pretty views aren’t enough. After my first trip where “high-speed Wi-Fi” meant “sometimes you can check your email,” I got serious about where I booked.

Great options in the US:

Boulder, Colorado: Walk to everything, mountain air, solid Wi-Fi.
Savannah, Georgia: Slow pace, tons of cafés for a work break.
San Diego, California: Great weather and loads of coworking spots.

International favorites:

Lisbon, Portugal: Late mornings, ocean views, friendly for digital nomads.
Medellín, Colombia: Affordable, full of remote workers, always springtime.
Chiang Mai, Thailand: Social, cheap, fantastic food.
Mexico City: Lively neighborhoods, plenty of spots to work and play.

Step 3: Book Like a Remote Pro, Not a Tourist

Your accommodation isn’t just a place to sleep. Check for:

Reliable, fast Wi-Fi (dig through recent reviews, message the host)
A real desk or table, plus a chair that won’t kill your back
Quiet surroundings—nobody wants to be on a call next to a busy bar
Good natural light for your sanity
Walking distance to coffee, food, or just a nice spot for a break

Pro tip: Search for listings that mention “laptop-friendly workspace” or “business-ready.”

Step 4: Plan a Schedule That Lets You Explore (Not Just Work)

Don’t just do your usual 40-hour week in a new place. Batch your calls or focused work in the mornings, so you can actually get out and see something afterward.

What worked for me in Lisbon:

Breakfast and a walk in a new neighborhood
Deep work or meetings late morning
Long, proper lunch (outside if possible)
Admin stuff in the afternoon
Beach or lookout for sunset, then dinner somewhere new

You’re not working less—you’re just working smarter and making space for adventure.

Step 5: Pack for Work and Play

This is not a “throw everything in a bag” trip. Here’s what I always bring:

Laptop and charger
Headphones (with mic for calls)
Portable laptop stand, wireless keyboard, and mouse
Power bank and universal adapter
Notebook for those “big idea” moments
Layers for weather, comfy clothes for both work and exploring

Nice extras:

Travel Wi-Fi hotspot
Noise-canceling earbuds
Extension cord
Ring light if you do lots of video calls

Keep your work gear in a separate pouch. Trust me—it helps you unplug at the end of the day, even if you’re staying in a tiny studio.

Step 6: Use Tools That Make Your Life Easier

Your toolkit should make you feel organized, not more stressed. A few basics:

Slack, Zoom, Google Meet for work
Notion, Trello, or ClickUp for keeping tasks in check
Google Drive or Dropbox for files
Apps like Rome2Rio or Omio to plan weekend escapes
AllTrails or Maps.me to find great walks or hikes nearby

And here’s the best hack I’ve found…

The One Travel App I Wish I’d Used Sooner: Axel

Here’s the honest truth: booking travel always stressed me out because I’d book a flight or hotel, then two days later the price would drop. Nothing’s worse than realizing you could have saved money if you’d just waited.

Now I use Axel. It’s not another booking platform—think of it as your AI-powered travel sidekick. After you book flights or hotels (wherever you want, with whoever you want), you just connect your email or forward your confirmations to Axel. From there, Axel quietly monitors your exact reservations 24/7. If it spots a price drop or a free upgrade, Axel rebooks you automatically. Same room, same policy, no hassle. You don’t have to do a thing, and you get a refund or an upgrade.

They offer a free trial, then it’s a simple subscription. I’ve saved real money this way—sometimes enough to pay for a special dinner or even a coworking pass for a week. Especially if you’re planning longer trips or lots of travel, this adds up quickly.

Workation Wisdom: Don’t Forget to Actually Live

The whole point of a workation is balance. Schedule work, but also schedule play—whether it’s a sunset walk, a café crawl, or a weekend day trip.

Let Axel keep an eye on your bookings so you can keep your eyes on the world around you. You’ll save money without even thinking about it, and you can spend your time doing what actually matters.

Happy travels (and happy working)! If you want a packing checklist or more destination ideas, just let me know.