Workation

Imagine answering emails with your toes in the sand, or wrapping up a video call just as the sun sets behind a mountain skyline. Sounds like a dream? Not anymore. Thanks to workation. Once considered a quirky buzzword, workations have evolved into a movement. Redefining how and where we work. They’re not just about trading your desk for a hammock; they’re about finding a rhythm where work fuels your wanderlust and wanderlust fuels your creativity. In this guide, we explore how workations became the ultimate blend of ambition and adventure. From their pandemic roots to their growing role in employee well-being and corporate culture, discover why this fusion of work and vacation isn’t a fleeting trend. It’s the future of how the world gets things done.​

What is a Workation, Really?

Picture this: you’re working on a spreadsheet while watching sunset over the ocean, or you’re attending a video call from a cozy mountain cabin instead of your usual desk. That’s a workation and it’s way more than just an oxymoron.​

A workation is when you combine “work” and “vacation” into one seamless experience. Employees continue their regular job responsibilities while temporarily working from a vacation-like destination instead of their usual office or home workspace. It’s not a day off. It’s not traditional remote work from your kitchen table. And it’s definitely not you abandoning your duties to sip piña coladas on a beach.​

Instead, it’s a structured work arrangement where you maintain your productivity standards and deliverables while getting the mental refreshment of a change in scenery. You’re still working, just in an environment that energizes you rather than drains you.​

What makes workations unique compared to other flexible work arrangements? It’s the intent behind the location. Remote work focuses purely on getting the job done from anywhere convenient. A workation, on the other hand, intentionally places you in a leisure-oriented destination to blend productivity with personal well-being.​

The concept exploded onto the scene during the pandemic when companies embraced remote work out of necessity. What started as a creative workaround transformed into a legitimate workplace perk that employees now expect and value. Today, workations represent a broader cultural shift in how, where, and why people choose to work.​

Why are Workations gaining Momentum?

The numbers tell a compelling story. According to recent data, over 65% of travelers in 2024 expressed interest in combining work and travel, particularly in markets like India. And it’s not hard to understand why. The appeal crosses industries, experience levels, and geographies.​

For employees, workations offer a legitimate escape from monotony. Working from the same desk every day is mentally exhausting. It’s repetitive. It kills creativity. Workations break that cycle by providing fresh inspiration and new perspectives that naturally boost productivity.​

Companies benefit too. The statistics are encouraging: flexible work arrangements are among the top three priorities for job seekers today, and 91% of employees worldwide prefer to work fully or almost completely remotely. For employers struggling with talent retention, workations are a powerful recruiting and retention tool. They signal that your company trusts employees to get the job done, regardless of location.​

The pandemic accelerated adoption by proving what many skeptics doubted. People are actually just as productive, if not more so, when they’re not chained to an office desk. Research from Stanford economist Nicholas Bloom found that employees working from home just two days a week were just as productive and likely to be promoted as their full-time office counterparts.​

The Different Flavors of Workation

Not all workations are created equal. Depending on duration, purpose, and whether it’s an individual pursuit or a group endeavor, workations take different forms.​

Individual Workations

An employee travels solo to a vacation destination while maintaining their regular job duties. It’s the most common type and typically the most flexible. An employee might take a week working from Barcelona, two weeks from a Thai island, or even a month-long digital nomad adventure spanning multiple countries. The key is that the individual handles the logistics and often covers their own expenses.​

Team Workations

Entire departments or project teams relocate together to strengthen collaboration, brainstorm on a specific initiative, or foster team bonding outside the typical office dynamic. These are often partially or fully funded by companies because they serve strategic business purposes. Team workations might involve a product team working from a retreat center for a week-long sprint, or a cross-functional group tackling a major project launch from a collaborative workspace in a new city.​

Extended Workations

Some employees blend vacation and work by extending their holiday. They take a scheduled vacation at a destination, then stay a few extra weeks while working remotely from the same location. It’s a practical way to maximize travel without taking excessive time off.​

Digital Nomad Workations

For the true wanderers, digital nomad workations mean combining travel and work on a near-permanent basis, frequently changing locations. These aren’t traditional employees taking occasional workations. They’re remote-first professionals who’ve embraced location independence as a lifestyle.​

The Real Benefits of Workations (And They’re Worth the Hype)

Productivity Isn’t a Myth. It’s Real

Here’s what might surprise skeptics: workations actually boost productivity. A change of scenery reduces monotony, which refreshes your mind and helps you approach tasks with renewed energy. Employees consistently report feeling more motivated, creative, and focused when working from inspiring environments.​

The research backs this up. People who work while on workations often integrate leisure with work strategically. They’ll tackle demanding cognitive work during peak mental hours, then take a beach walk during an afternoon slump, returning refreshed for the evening deliverables. That natural rhythm often produces higher-quality output than grinding away in a stale office environment.​

Mental Health and Burnout Prevention

Burnout is real in today’s workplace, and workations help combat it directly. Traditional vacation means unplugging completely, which can feel forced or incomplete for high-achievers. Workations solve this by allowing you to maintain some work engagement while actually changing your environment and routine.​

According to research by IWG, 66% of hybrid workers reported improvements in their mental health due to increased personal time, which includes breaks and genuine leisure activities. When you’re working from a beautiful location, you naturally take more breaks. You go for walks. You embrace local experiences. These activities genuinely reduce stress without requiring you to sacrifice your job entirely.​

Enhanced Creativity and Fresh Perspectives

New environments spark new ideas. Travel exposes you to different cultures, approaches, and ways of thinking. When you’re working from a dynamic location rather than your familiar home office, your brain works differently. You approach problems from fresh angles, collaborate more openly with teammates across time zones, and return to regular work with renewed creative energy.​

Better Work-Life Balance (Without Guilt)

Here’s the honest tension: traditional vacation means completely disconnecting from work, which can feel guilty for dedicated professionals. Workations flip the script. They let you enjoy personal time, explore new places, and relax without the anxiety of neglecting your responsibilities or facing a mountain of work upon return.​

Retention and Talent Attraction

For employers, the benefits are equally compelling. Flexible work arrangements are the difference between retaining your best talent and losing them to competitors. A 2024 survey found that 39% of employees would consider resigning if their employers weren’t flexible about remote work. Offering workations signals that your company trusts employees and values their well-being. Both powerful retention drivers.​

Beyond retention, workations make your company attractive to a new generation of workers who expect flexibility as a baseline benefit, not a special privilege.​

The Challenges Are Real Too

Maintaining Productivity When Paradise Is Distracting

Beaches, tourist attractions, and the novelty of a new place can absolutely derail focus. Not everyone has the discipline to prioritize work when there’s snorkeling and exploring to do. For some employees, a workation becomes an excuse to underperform, and for managers, distinguishing between genuine distractions and deliberate procrastination is tricky.​

Time Zone and Communication Complications

If your workation takes you across the globe, time zone differences create real coordination headaches. A marketing manager working from Bali while their team is in London might miss critical meetings or feel pressure to work odd hours. Team synchronization becomes more complex, and asynchronous communication requires discipline.​

Security and Data Protection Concerns

This one keeps IT directors up at night. Employees accessing company networks from public WiFi in coffee shops and resorts introduce significant cybersecurity risks. Working from unfamiliar locations with uncontrolled internet access multiplies the potential for data breaches, phishing attacks, and unauthorized access to sensitive information.​

Companies must enforce security protocols like VPNs, multi-factor authentication, and regular employee training on data protection practices. The risk isn’t hypothetical. It’s a genuine operational concern that requires robust policies and employee education.​

The Work-Life Boundary Blur

Here’s the philosophical challenge: workations intentionally blur the line between work and personal life. For some employees, this is liberating. For others, it’s the opposite. If you can’t truly disconnect from work, even in a vacation setting, you might not get the mental restoration that vacation traditionally provides. Some workers need that clear boundary between work hours and personal time to avoid burnout.​

Not All Roles Are Workation-Friendly

Reality check: some jobs just can’t be done remotely. Manufacturing, in-person healthcare, on-site construction, and collaborative roles requiring constant face-to-face interaction don’t translate well to workations. This creates disparities. Some teams can take regular workations while others can’t, which can breed frustration and resentment among staff.​

Costs Can Escalate Quickly

While workations might save commuting expenses, they create new financial burdens. Travel, accommodation, meals, and the general cost of living in tourism-oriented destinations add up fast. For self-funded workations (the most common model), employees bear these costs themselves. For companies offering partially or fully funded workations, budget implications can be significant.​

Three Models: Who Pays for Workations?

The funding model directly impacts how workations operate in your organization.​

Self-Funded Workations

Self-Funded Workations represent the most common approach. Employees choose their destination and cover all expenses themselves. Travel, accommodation, meals, and internet upgrades. This gives maximum employee autonomy but places financial burden on the individual. It’s ideal for organizations wanting to offer flexibility without significant budget implications.​

Partially Covered Workations

Partially Covered Workations represent a middle ground. Companies offer financial support, bonuses, or expense reimbursement to encourage the practice. Perhaps they cover accommodation but not travel, or they provide a set stipend for approved workation destinations. This approach signals company support while maintaining fiscal responsibility.​

Company-Funded Workations

Company-Funded Workations occur in specific strategic contexts, particularly for team retreats, offsites, and projects requiring intensive collaboration. A software company might fund a week-long workation where the product team relocates to a resort with excellent meeting facilities to launch a major feature. The investment pays dividends in team alignment, shared purpose, and focused output.​

Making Workations Work: Best Practices for HR and Managers

Successfully implementing workations requires clear policies, intentional communication, and realistic expectations. Here’s what actually works.​

Establish a Clear, Written Policy

Ambiguity breeds problems. Your workation policy should explicitly define:

• Eligibility criteria (tenure, role type, performance standards)
• Approval process and timeline for requests
• Frequency and duration limits (e.g., “employees can take up to three weeks per year”)
• Destination restrictions or approvals needed
• Which positions qualify and which don’t
• Expected work hours and availability requirements
• Communication protocols and check-in frequency
• Security requirements (VPN usage, data protection standards)
• What happens if productivity suffers
• Tax and employment law compliance

The policy needn’t be rigid, but it should be transparent and consistently applied.​

Provide Tools and Training

Employees working from vacation destinations need the right infrastructure. This includes:

• Reliable company laptops or devices suitable for remote work
• VPN access for secure network connections
• Stipends for internet upgrades or coworking spaces if needed
• Collaboration software training
• Cybersecurity best practices training
• Access to IT support for technical issues

Equally important is training employees on security protocols. They need to understand why public WiFi poses risks, how to identify phishing attempts, and why data protection matters even when they’re “on vacation.”​

Define Clear Expectations and Goals

Clear expectations prevent misunderstandings. Before approving a workation, establish what success looks like:

• Specific deliverables expected during the workation period
• Communication requirements (daily standups, weekly check-ins, always available for urgent issues)
• Response time expectations for emails and messages
• How time zone differences will be managed
• Whether flexibility on work hours is permitted (often it is, but within reason)
• Metrics for measuring productivity

The goal isn’t surveillance. It’s clarity. When employees know precisely what’s expected, they typically deliver.​

Regular Check-Ins, Not Micromanagement

Trust matters. While periodic check-ins are appropriate, constant monitoring destroys morale and defeats the purpose of a workation. Strike a balance with:

• Weekly video calls to discuss progress and address blockers
• Asynchronous updates on major milestones
• Accessible communication for genuine urgencies
• Respect for their workation experience during designated off-hours

The key is managing by outcomes, not activity. If deliverables are met and communication is solid, let them enjoy their location.​

Prioritize Security Above Convenience

Security isn’t optional. Mandate that employees:

• Use VPN connections at all times when accessing company resources
• Enable multi-factor authentication on all accounts
• Use company-provided WiFi hotspots instead of public networks when possible
• Never work from truly public locations (libraries, coffee shops) with sensitive data
• Report any suspicious activity or security concerns immediately

Companies should provide employees with security tools and resources, not hope they’ll figure it out independently. This is especially critical if workations span multiple countries with varying security standards.​

The Legal and Tax Landscape

Here’s where workations get complicated, and honestly, this is where you should consult with legal and tax professionals who understand your specific jurisdiction.​

Tax Obligations

After a certain duration in a foreign country, employees may become subject to local taxation. The thresholds vary significantly:

• Some countries trigger tax obligations after 30 days
• Others use 90 days as the threshold
• Social security implications often kick in separately

The rule of thumb: if workations extend beyond three weeks in a foreign country, employer and employee should verify local tax obligations with a tax professional. Failing to comply with foreign tax law exposes both the employee and the company to penalties.​

Employment Law Compliance

Depending on the workation destination, different employment regulations may apply. A Swiss company allowing employees to work from Spain for a month might suddenly face Spanish employment law considerations. Some countries require:

• Specific work permits or visa classifications
• Compliance with local employment standards
• Adherence to local working hour regulations
• Registration with local tax authorities if the company establishes a “permanent establishment”

This isn’t a small detail. Employment law violations can result in significant penalties and liability. Smart companies clarify these implications upfront with local legal counsel, particularly for longer or repeated workations.​

The German and Swiss Examples

Germany provides useful context: under German employment law, employees have no legal right to workations. The employer determines the work location, often explicitly defined in the employment contract. Working abroad without approval could violate the employment contract and result in warnings or termination.​

However, employers can grant workations at their discretion by amending employment agreements or creating supplementary workation agreements. Swiss law similarly permits workations but requires clear agreements addressing duration, location, work hours, communication expectations, tax compliance, and social security obligations.​

The takeaway? Workations are generally allowed, but they require intentional legal and financial structures, especially when crossing international borders.​

Workation vs. Remote Work vs. Work-From-Anywhere: What’s the Difference?

These terms get thrown around interchangeably, but they’re actually distinct concepts.​

Remote work simply means performing your job outside the office. You work from home, a coffee shop, or your coworking space. The location is secondary. The goal is pure productivity. Remote work can be permanent or temporary, and it doesn’t necessarily involve travel or leisure-oriented destinations.​

Work-from-anywhere is a policy framework stating that employees aren’t required to ever visit the office. They can work from home, while traveling, or from anywhere they choose. It’s location-agnostic and often permanent. A workation can be part of a work-from-anywhere policy, but the two aren’t synonymous.​

Workation specifically blends work with leisure in a destination chosen for its vacation appeal. Duration is typically shorter (a few weeks maximum), and the explicit goal is balancing productivity with personal renewal. You’re not just working from elsewhere, you’re intentionally creating an experience that combines work and relaxation.​

The distinctions matter because each requires different policies, expectations, and management approaches. A company with a work-from-anywhere policy might prohibit extended workations for liability reasons, while simultaneously allowing permanent remote work from anywhere globally.​

Real-World Implementation: What Companies Are Actually Doing

Leading companies across industries have embraced workations as competitive advantages.​

Pinterest’s PinFlex program is particularly progressive. Full-time employees with six months tenure can work outside their home country for up to three months per year. Those with less tenure get 30 days. The policy is specific, generous, and shows meaningful trust in employee judgment.​

EZ Texting allows employees up to 20 U.S. business days or 10 international business days annually for work-from-anywhere arrangements, complete with home office stipends. It’s a clear allocation that employees can plan around.​

DuckDuckGo, fully remote with employees across 15+ countries, provides office supply allowances and coworking space reimbursement up to $500 monthly. This infrastructure investment ensures remote workers (and workation takers) have the tools to succeed.​

Automattic, the company behind WordPress, offers minimum 25 days annual leave plus a professional development budget. With 2,000 employees across 90 countries, they’ve systematized global remote work effectively.​

The pattern is clear: companies succeeding with workations provide structure, resources, and clear policies rather than hoping employees self-manage.​

The Workation Advantage for Payroll and HCM Integration

This is where workations intersect with critical HR operations and why they matter for companies using integrated HCM and payroll systems.​

Workations complicate payroll in specific ways. Tax withholding obligations may change based on work location. Social security contributions might differ. Time tracking and overtime calculations could be affected by time zone differences. Benefits eligibility might depend on location.​

For companies like BrynQ focused on seamless payroll integration across global HCM systems, workations represent real operational complexity. When an employee works from three countries in six months, payroll systems must accurately track and calculate:

• Appropriate tax withholding by jurisdiction
• Correct social security contributions
• Proper overtime or holiday pay based on local law
• Accurate benefits administration

Smart HCM systems anticipate this complexity. They allow managers to designate workation periods, flag location changes, and automatically adjust payroll calculations accordingly. They integrate with tax compliance tools to ensure no missed obligations. They coordinate with global benefits platforms to maintain coverage continuity.​

This is why workation policies matter operationally. They’re not just HR nicities, they’re payroll and compliance necessities.​

Making the Workation Decision: Is It Right for Your Organization?

Workations aren’t universally appropriate. Before implementing one, honestly assess whether it fits your context.​

Workations make sense if:

• Your organization values outcomes over presence
• Your employee base includes roles that can genuinely be done remotely
• You have the infrastructure (VPN, collaboration tools, IT support) to support it
• Your leadership culture trusts employees to work autonomously
• You’re competing for talent in competitive markets where flexibility is table stakes
• Your company operates across multiple time zones already

Workations are problematic if:

• Your culture heavily emphasizes in-office presence and face-to-face collaboration
• Most roles require hands-on, in-person work
• Your infrastructure isn’t prepared for distributed teams
• Your industry faces strict regulatory requirements about work location
• Your management style relies on direct supervision and visible presence
• Your company can’t afford the complexity of multi-jurisdictional tax and employment compliance

There’s no shame in concluding workations aren’t right for your organization. Better to be honest than implement a policy that creates more problems than it solves.​

But for organizations that embrace them thoughtfully, workations represent more than a perk. They signal that you trust your people, respect their well-being, and recognize that the best work often happens when employees have the freedom to thrive on their own terms.​

Final Thoughts: The Evolution of Work

Workations aren’t a fad. They represent a fundamental shift in how we think about work, location, and employee well-being. The pandemic proved that location doesn’t determine productivity. Structure, trust, and clear expectations do.​

For HR managers navigating these shifts, the key is intentionality. Thoughtful policies, clear communication, proper infrastructure, and ongoing management create workation programs that genuinely benefit both employees and organizations. Haphazard implementation creates chaos.​

As companies compete harder for talent and employees increasingly expect flexibility as a baseline, workations have become a strategic necessity rather than a nice-to-have perk. The question isn’t whether to offer them, but how to implement them thoughtfully, securely, and compliantly.​

The future of work isn’t about being tethered to a desk. It’s about being trusted to deliver excellent work from wherever that work happens best. For many employees, that’s a beach, a mountain, or a cozy café in a new city. And if the work gets done, the creativity flows, and the employee is happier and healthier? That’s a win for everyone.​