How to plan a workation that's actually worth taking

Getting permission is one problem. Actually having a good time is a different one, and it’s the one people underestimate.

The failure mode is predictable. You land somewhere exciting, keep your normal workload, try to sightsee at lunch, and end up doing both badly. Then you fly home tired and conclude workations don’t work.

They do. But the planning is different from a holiday, and mostly it comes down to four decisions.

(If you haven’t cleared it yet, that conversation has its own guide.)

1. Time zone decides everything else

This is the decision that makes or breaks the trip, and people pick it last.

You want to finish work with daylight left. That’s the whole point — the trip happens in the hours after you log off.

Working U.S. hours from Latin America, you’re done between 5 and 7pm local, with an evening in front of you. Working U.S. hours from Europe, you start mid-afternoon and finish near midnight. The city is closed and you saw none of it.

The rule: go east and you lose evenings; go west or stay level and you keep them. For a U.S.-based worker, Colombia, Mexico, and Panama are the easy wins. Europe works properly only if you can shift your hours or take real time off.

2. Stay a week minimum, ideally two

A workation is not the trip where you see three cities.

Five working days already eat most of a week. Moving costs you a half-day each time, plus finding a new café, a new supermarket, a new route. Do that twice and the trip is over before you knew where anything was.

One base. Day trips at the weekend. That’s the format that works.

The longer stay also fixes the cost. Weekly and monthly rates drop sharply, which is covered properly in the guide on solo travel costs.

3. Book for the work, not the photos

The single most common mistake: booking somewhere beautiful with nowhere to sit.

Before you book, check three things.

• A real desk and a real chair. Not a stool at a kitchen counter. You’ll be there 40 hours.
• Wifi you’ve verified. Listings claim fast wifi routinely. Ask the host for a speed test screenshot, or pick somewhere whose whole business depends on it.
• A door, or a plan for calls. If you take meetings, a shared dorm won’t work.

Colivings are built precisely for this — desks, tested wifi, call booths, and people around when you log off. Disclosure: I’m a part-owner of a coliving space. I’d recommend the category regardless, but you should know that.

Otherwise a whole apartment with a workspace, plus two or three cafés scouted in the first days, does the job.

4. Protect a few days properly

The best version of this isn’t five working days evenly spread. It’s working days with real time off bolted to one end.

Take the Friday and Monday around a weekend and you get four uninterrupted days in a place you already know your way around. That beats a four-day trip where two days go to arriving and orienting.

Front-load or back-load. Don’t sprinkle half-days through the week — you’ll neither work nor rest.

What a good week actually looks like

Work the hours you’d work at home. Take lunch outside, every day. Log off and go somewhere you haven’t been, even for an hour. Keep one weeknight completely free.

Then use the weekend like a proper traveller.

That’s it. It’s less cinematic than the version on Instagram, and it’s the reason people come home wanting to do it again.

The honest caveat

A workation is not a holiday, and pretending otherwise is how people come home more tired than they left. You get better evenings and a different weekend. You do not get your working hours back, and planning as though you will is the main way this goes wrong.