Your First Workation: A Step-by-Step Guide for Beginners

So you want to try a workation. Maybe a colleague came back from Lisbon glowing about how productive they were. Maybe you’re tired of staring at the same home office walls. Whatever the reason, you’re curious, but you’re not sure where to start.

Good news: your first workation doesn’t need to be complicated. With some planning upfront, you can avoid the most common beginner mistakes and set yourself up for a trip that’s both productive and genuinely enjoyable. Here’s how, step by step.

Step 1: Talk to Your Employer (Yes, First)

This is where most people get the order wrong. They book flights, find an apartment, and then casually mention to their boss that they’ll be working from Bali next month. Don’t do that.

How to approach it:

• Check if your company already has a remote work or workation policy. Many companies now do, especially post-2020.
• If there’s no formal policy, frame it as a trial. “I’d like to try working remotely from [destination] for [duration]. Here’s how I’ll make sure it doesn’t affect my work.”
• Address the obvious concerns upfront: time zone overlap, availability for meetings, internet reliability.
• Start with a short trip (1-2 weeks) to build trust.

Key things to clarify:

• Are there countries where you’re not allowed to work for tax or legal reasons?
• Do you need to be available during specific hours?
• Is there a maximum duration?
• Does the company need to register you for social security or tax purposes in that country?

Pro tip: Don’t ask “Can I do a workation?” Ask “Here’s my plan for staying productive while working from X. Does this work for the team?” It’s a much easier yes.

Step 2: Choose Your Destination

For your first workation, don’t overthink this. Pick somewhere that minimizes risk and maximizes your chances of a good experience.

Criteria for a good first workation destination:

• Same or similar time zone as your team. A 1-2 hour difference is fine. A 7-hour difference on your first try is asking for trouble.
• Reliable infrastructure. Western and Southern Europe, established digital nomad hubs in Southeast Asia, or major cities in the Americas.
• Affordable enough that the trip doesn’t stress you financially.
• A place you genuinely want to be. This sounds obvious, but pick somewhere that excites you. Motivation matters.
• Good internet reputation. Check nomad forums and review sites for WiFi reliability reports.

Great first workation destinations from Europe: Lisbon, Barcelona, Split, Athens, Tenerife. All have reliable internet, are easy to reach, and the time zone difference is minimal.

If you’re more adventurous: Bangkok, Chiang Mai, Bali, Medellín. Excellent nomad infrastructure but bigger time zone shifts if your team is in Europe.

Step 3: Plan Your Timeline

Timing matters more than you’d think. Here’s a rough planning timeline:

6-4 weeks before:

• Get employer approval.
• Book flights (prices jump closer to departure).
• Book accommodation (look for places with workspace photos and WiFi speed mentions in reviews).

2-1 weeks before:

• Research local SIM card options and coworking spaces.
• Set up a VPN if you’ll need one.
• Inform your team of your schedule and availability.
• Check if you need any travel insurance adjustments.

Day before departure:

• Download offline maps and essential documents.
• Charge all devices.
• Pack your work essentials (see Step 5).

First day at destination:

• Buy a local SIM card.
• Test your accommodation’s WiFi (speed test from your workspace).
• Locate the nearest coworking space as a backup.
• Set up your workspace before doing anything else.

Step 4: Book the Right Accommodation

Your accommodation is your primary office. Treat it that way.

Must-haves:

• A proper desk and chair (not just a kitchen table). Look at the photos carefully.
• WiFi with good recent reviews. Filter for mentions of speed and reliability.
• A quiet location. Street-facing apartments in party districts are not ideal for Monday morning calls.
• Good natural light. You’ll be spending a lot of time here.

Nice-to-haves:

• A separate room or area for work (so you can “leave the office” at the end of the day).
• A kitchen (saves money and lunch-break time).
• Close to a coworking space or cafes with WiFi (your backup plan).

Booking tips:

• Message the host beforehand and ask about WiFi speed and desk setup.
• Book slightly longer than you think. A two-week workation is more relaxed than one week. You have time to settle in.
• Arrive on a weekend so you can explore and set up before your first workday.

Step 5: Pack Smart

You don’t need to bring your entire home office. But a few items make a huge difference.

Work essentials:

• Laptop (obviously) and charger.
• Noise-cancelling headphones. Non-negotiable.
• A foldable laptop stand (for ergonomics).
• Universal power adapter.
• A compact external keyboard and mouse.

Connectivity:

• Your phone (for hotspot backup).
• A short ethernet cable (some accommodations have wired connections that are much faster than WiFi).

Documents:

• Passport and copies (digital and physical).
• Travel insurance details.
• Company approval documentation (if applicable).
• Emergency contacts and your nearest embassy address.

What to leave behind:

• A portable monitor (save this for future workations, it’s overkill for your first).
• Multiple screens worth of gear. Keep it light and simple.

Step 6: Set Your Routine Early

The biggest trap on a first workation is treating it like a holiday with occasional emails. Or the opposite: working 12-hour days because you feel guilty about being somewhere nice.

What works:

• Set clear work hours and communicate them to your team.
• Start your first workday with your most important task (prove to yourself it works).
• Take a real lunch break. Go outside. Eat somewhere local.
• End your workday at a set time. Close the laptop. Go explore.
• Have at least one “anchor” for your routine (morning coffee at the same place, an evening walk, a gym session).

What doesn’t work:

• “I’ll figure out my schedule as I go.” You won’t. You’ll either overwork or underwork.
• Working from bed. Ever.
• Trying to see every tourist attraction in your first week. The sights will still be there on the weekend.

Step 7: Handle the Unexpected

Things will not go perfectly. That’s fine. Here’s how to handle the common surprises:

• WiFi goes down: Switch to your phone hotspot. Message your team. Head to a coworking space if it’s a longer outage.
• You’re less productive than expected: Normal for the first 2-3 days. You’re adjusting. It gets better.
• You feel isolated: Find a coworking space, even just for a day. The social contact helps.
• Work-life balance is off: Physically leave your workspace at the end of the day. Go to a restaurant, a park, or just take a walk.

The Most Important Tip

Don’t aim for perfection on your first workation. Aim for “good enough to want to do it again.” You’ll learn more from actually going than from any amount of planning. Book the trip, set up the basics, and figure out the rest as you go.

Your second workation will be better than your first. Your fifth will feel like second nature. But none of that happens until you take the first step.