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

Blending work and travel used to be a dream. Now, it’s a strategy.

Enter the “workation”: part vacation, part remote work setup, and — when done right — the best of both worlds. You explore somewhere new without burning through all your PTO. You stay productive without being stuck in your living room. And maybe for the first time, you wrap up a workday and walk straight onto a beach, a trail, or a cobblestone street you’ve never seen before.

But there’s a catch: poorly planned workations lead to stress, burnout, and missed opportunities.

This guide shows you how to do it right — with practical planning strategies, destination ideas, productivity hacks, and even the best times to actually take one.

Why Take a Workation?

Because you're not just trying to escape — you're trying to stay inspired. Workations offer a balance that can actually make you better at your job and happier in your day-to-day life.

Benefits include:

  • A shift in scenery that boosts creativity
  • More flexible use of remote work policies
  • The chance to explore without fully unplugging
  • Lower travel costs (no need to rush in a short window)

Done well, a workation feels like a sustainable way to make travel part of your lifestyle, not a disruption from it.

Step 1: Know When You’re Actually Ready

Workations are not for everyone — or every work schedule. Ask yourself:

  • Can I maintain my core responsibilities remotely?
  • Do I have autonomy over how I schedule my day?
  • Is my internet dependency low enough to survive hiccups?
  • Can I actually take a few hours to explore?

If you're in back-to-back meetings from 9 to 6, a workation might feel more like working in a prettier prison. But if you have flexible hours or deep-focus tasks, you’re in the sweet spot.

Step 2: Choose a Workation-Ready Destination

Not every beautiful place is ideal for remote work. You want stability, comfort, connectivity — and just enough excitement to spark joy, not distract you entirely.

Ideal Domestic Workation Spots

Boulder, Colorado
Walkable downtown, fast Wi-Fi, and mountain trails within minutes.

Savannah, Georgia
Charming, calm, and full of cafes — ideal for slow mornings and productive afternoons.

Santa Fe, New Mexico
Art, adobe, and surprisingly strong infrastructure.

San Diego, California
Perfect climate, beach breaks, and coworking spaces galore.

Best International (But Easy) Picks

Lisbon, Portugal
A digital nomad favorite. Late-start culture, ocean views, and excellent espresso.

Medellín, Colombia
Low cost of living, coworking communities, and spring-like weather year-round.

Chiang Mai, Thailand
Famous for remote workers. Affordable, social, and rich in nature and food.

Mexico City, Mexico
Big city energy with vibrant culture and plenty of space to focus (when needed).

Step 3: Book with Intention, Not Just Price

You’ll be working from here — that changes everything.

When booking accommodation, prioritize:

  • Reliable, high-speed internet (check reviews or message the host)
  • A real desk or table with a proper chair
  • Noise levels (you don’t want to work next to a bar or highway)
  • Natural light — it helps with mood and productivity
  • Walkability to coffee, groceries, or parks for breaks

Bonus: Some places list themselves as “workation-ready” on Airbnb or Selina. Look for “laptop-friendly workspace” or “business-ready.”

Step 4: Build a Schedule That Balances Work + Discovery

The biggest mistake most people make? Cramming their regular 40-hour work week into a new setting… and then wondering why they don’t feel rested or inspired.

Instead:

  • Batch calls in the morning so you can explore later
  • Block 90-minute focus sessions with clear goals
  • Use local time zones to your advantage — sometimes you’ll get free mornings or evenings
  • Take real lunch breaks (outside!)
  • Keep 1 full day off for real adventure

Example schedule in Lisbon (for someone working East Coast U.S. hours):

  • 8–10 a.m.: Stroll, breakfast, walk a new neighborhood
  • 10 a.m.–1 p.m.: Calls or deep work
  • 1–2 p.m.: Long lunch
  • 2–5 p.m.: Emails, follow-up, admin
  • 5–7 p.m.: Head to the beach or a lookout for sunset

You’re not working less — just smarter.

Step 5: Pack With a Remote Setup in Mind

Workation packing is part suitcase, part mobile office. Make space for:

  • Laptop and charger
  • Headphones with mic (Zoom-friendly)
  • Portable laptop stand + wireless keyboard/mouse (for posture)
  • Universal adapter
  • Power bank
  • Notebook for ideas, notes, or planning
  • Lightweight clothing that’s comfy for work and play

Optional but useful:

  • Travel Wi-Fi hotspot
  • Noise-canceling earbuds
  • Extension cord or plug splitter
  • Ring light (if video calls matter)

Pro tip: Put work gear in a separate pouch so you can “put it away” when off duty — even if you're in a studio Airbnb.

Step 6: Choose Tools That Work Everywhere

Connectivity and organization are everything.

Here’s a basic toolkit for workations:

  • Slack / Zoom / Google Meet – for team comms
  • Notion / Trello / ClickUp – for tasks
  • Google Drive / Dropbox – for cloud storage
  • Trail Wallet / Revolut – for budgeting
  • Rome2Rio / Omio – for weekend travel planning
  • AllTrails / Maps.me – for unplugged exploration

And of course, if you’re booking your travel in advance…

Don’t Forget This Workation Hack: Axel

If you’re booking flights and hotels, you want to keep costs low — but who has time to recheck prices every few days?

That’s where Axel shines.

Axel monitors your bookings after you’ve paid. If prices drop, Axel rebooks automatically and gets you a refund — without any effort on your part.

It’s like a silent travel assistant who’s always scanning for deals while you focus on work (or wander the streets of a new city). Especially for longer or frequent trips, this adds up fast.

Weekend Bonus: Turn Your Workation Into a Mini Escape

One of the joys of workations is that you’re already there. So make the most of weekends or days off:

  • Book a 1-night getaway to a nearby nature spot
  • Take a local cooking class or language intro
  • Join a walking tour or photography meetup
  • Go café-hopping in a different neighborhood
  • Take the train somewhere just for lunch

Even 24 hours of “travel” in the middle of your work week can recharge your brain more than a week of vacation on the couch.

Real-World Workation Itinerary: Mexico City (7 Days)

Monday–Friday:
Stay in Condesa. Mornings at Blend Station café, work in Selina coworking until 5. Evenings for exploring Parque México, tacos al pastor, or rooftop bars.

Saturday–Sunday:
Take a day trip to Teotihuacán or hop a cheap flight to Oaxaca for food and culture.

Total cost: ~$800 with flight, lodging, food, coworking, and a weekend trip included.

Common Workation Mistakes to Avoid

  • Not checking Wi-Fi before booking — ask hosts or read recent reviews.
  • Over-scheduling work — remember, new environments drain more energy.
  • Not setting work boundaries — colleagues won’t know you’re on a workation unless you say so.
  • Skipping insurance — you’re still traveling. Get coverage for gear, health, and delays.
  • Thinking you’ll sightsee after work every day — plan for intentional breaks, not leftovers.

Final Thoughts: Redefine How You Travel — and Work

A workation isn’t just a trend — it’s a reflection of how the world is shifting. Flexibility is the future. The office is wherever your laptop opens. And the boundaries between “work” and “life” are more fluid than ever.

Done right, a workation can help you reconnect with your energy, your purpose, and the wide-open world outside your inbox.

So go ahead — answer that email from a rooftop in Lisbon. Just don’t forget to look up once in a while.

And let Axel handle the boring part: watching your prices, rebooking your deals, and saving you money — so you can focus on what matters.