A workation is a trip where you keep doing your normal job while you spend time somewhere new. This guide shows how to plan one in seven steps, starting with trip length and ending with a weekly work schedule. Along the way it covers employer approval, visa and tax checks, wifi, and insurance.
Seven steps to plan a workation
1. Choose a trip length and a time zone that fit your job
Trip length and time zone decide how much planning the rest of the trip needs. A short trip in a nearby time zone is the simplest place to start.
- Length: A 2022 survey of 1,117 US workers by Passport-Photo.Online asked about workation length. Of the trips reported, 36% lasted one to two weeks, 32% lasted three to four weeks, and 13% lasted more than a month.
- Time zone: Medellin stays on UTC-5 all year. US Eastern time is UTC-5 in winter and UTC-4 in summer, so New York is one hour ahead of Medellin only in summer.
- Bigger differences: A UK team that works 9:00 to 17:00 in summer time covers 16:00 to midnight in Bali, which stays on UTC+8 all year.
A difference of one or two hours can fit inside a normal workday. Larger differences mean early mornings or late nights. The guide to client meetings across time zones explains how to manage them.
2. Get approval from your employer in writing
Employers decide whether a workation can happen, and many are open to it. A Mercer survey reported in January 2024 found that 78% of companies allow international remote work, either under a set policy or case by case.
- Allowed days: The HR platform Aivy reports that many companies cap workations at 30 to 90 days a year. Ask which limit applies to your role.
- Notice: Deep, a European connectivity provider, suggests giving one to two months of notice. Early notice gives HR time to check tax and visa questions.
- Written record: The coworking operator Officeclub recommends recording the destination, dates, and working hours in a written agreement.
- Equipment: Some employers do not want work laptops used abroad or on hotel wifi, according to Generali Travel Insurance. Ask about both before packing.
Freelancers have no employer to ask, although client contracts can set rules about where work takes place.
3. Check the visa and tax rules for the country
Visa rules differ by country, and short workations usually raise fewer tax questions than long ones.
- Tourist visas: According to Quartz, tourist visas typically prohibit paid work. Some countries allow remote work for a foreign employer, some ban it, and many state no policy. Penalties range from nothing to fines, entry bans, and deportation.
- Digital nomad visas: About 55 countries offer a dedicated digital nomad visa in 2026, according to RelocateMe, and the count passes 60 when similar remote work permits are included. A visa like this can suit a stay of several months better than a two-week trip.
- Tax: Law firm Baker McKenzie notes that short workations often do not change tax status or social security cover. Tax residency can depend on the length and purpose of the stay and on personal ties to the country, according to CohnReznick.
- EU social security: An A1 certificate shows which country’s social security system applies to a worker. The EU is revising these rules in 2026, so HR should confirm the current position.
The guide to digital nomad visa vs tourist visa explains which one a given stay needs. Rules also differ by passport, so the destination’s official immigration site is a reliable place to confirm them.
4. Book a stay with a real desk and tested wifi
The place to sleep and the place to work can be the same building or two different ones. The internet needs a check before payment either way.
- Wifi proof: Airbnb adds a fast Wi-Fi label to listings that test at 50 Mbps or above in its app. Asking any host for a recent speed test that shows upload speed is reasonable, since video calls use both directions. The guide to checking wifi speed before booking a stay covers the tools.
- Coworking: Day and week passes suit short trips. A July 2024 review of the Outsite Cowork Cafe in Lisbon listed a weekly pass at €70. More options appear in the guide to coworking spaces with day passes.
- Coliving: Freaking Nomads reports that many coliving spaces set a minimum stay of 7 or 14 nights, so confirm it before booking flights. In Lisbon, Casa Basilico data cited by the same site puts coliving at about €800 to €1,800 a month all in. A comparable long-stay Airbnb costs €1,400 to €2,200 before coworking.
- Organized programs: Hacker Paradise runs four-week trips with two-week options, according to a June 2026 roundup. An older review listed two-week prices from $1,550, so confirm current rates. Nomad Cruise charged $986 to $1,160 for nine nights in an Ubud suite in 2025, with coworking, two dinners, and evening events included. More choices appear in the guide to the best digital nomad retreats.
If the stay has no desk, the guide to a mobile home office in a hotel or Airbnb explains how to set up a workable space.
5. Prepare internet back-ups, security, and insurance
A dropped connection or a lost laptop can stop work for days, and a short trip leaves little time to fix either.
- Back-up data: A travel eSIM or local SIM can act as a hotspot if the stay’s wifi fails. The comparison of eSIM vs local SIM and portable hotspots covers the choices.
- Security: Public wifi in cafes and airports can put work accounts at risk. The guide to cybersecurity tips for public wifi explains how to protect them.
- Insurance: MoneySuperMarket notes that standard travel policies with personal liability cover usually exclude incidents at work. Eskimo, another insurance guide, says work-equipment exclusions and single-item limits can reduce a laptop payout. The guide to travel insurance with remote work coverage explains what to check.
6. Split each week into work days and free days
Workation days count as work days, so the schedule should show which days are work and which are free.
- Leave days: LeaveBalance notes that employees can take annual leave for part of a workation, such as working Monday to Wednesday and taking Thursday and Friday off.
- Condensed weeks: The business coaching firm ActionCoach suggests grouping work into Tuesday to Thursday to create long weekends.
- Arrival day: Light work on the first day leaves room for travel fatigue. The guide to beating jet lag while hitting deadlines covers how to handle both.
- Routine: A fixed start time and a fixed work spot can keep the week steady in a new place. The guide to a consistent routine while traveling for work goes further.
- Availability: Fiverr advises telling clients and managers which time zone applies and when they can expect replies.
Deep warns that the line between work and leisure can blur, so a clear stop time each day helps. Free days are the reason for the trip, so they deserve a plan. You can look up retreats and weekend trips near your base on FlyBibe before the trip starts.
7. Book flights and run a final check
Flights come after the employer, visa, and stay are confirmed. The guide to the best time to book international flights covers timing. A final check a week before departure covers the points below.
- Employer: Written approval is saved and the dates match.
- Visa: Entry and work rules for your passport are checked on an official site.
- Stay: The minimum nights are confirmed and the wifi test result is saved.
- Insurance: The policy covers work equipment and the full trip length.
- Calendar: Work hours and time zone are visible to the team.
One mistake to avoid: leaving the employer out
In a June 2026 survey of 2,000 employed Americans commissioned by Mews, 29% said they had worked remotely on vacation without telling anyone at work. Leaving the employer out creates risks for both sides.
- Hidden trips: The employer carries legal and financial liability for tax, payroll, and right-to-work compliance, even when the employee starts the request, according to the compliance firm Work From Anywhere. LeaveBalance adds that working from an undisclosed location can breach an employment contract.
- Long stays: Right-to-work and social security rules can apply from day one, according to Work From Anywhere. Tax residency and company tax exposure build over weeks or months. A stay of several months may fit a digital nomad visa better than a workation.
Start planning your workation
A good workation needs a few checks done early: employer approval, visa and tax rules, tested wifi, and a clear weekly schedule. With those in place, the free days can go to the part of the trip worth traveling for. When you are ready to pick a base, find remote-friendly tours and stays on FlyBibe and plan the time away from the laptop.