Ever dreamed of sipping coconut water by the beach while checking off your to-do list? That’s the charm of a workcation, where you get things done while soaking in new views and a fresh mindset.
But a productive workcation doesn’t happen by accident. If you show up without a plan, you might end up working all day in a hotel room with spotty Wi-Fi and no time to enjoy the place you flew across the world to see.
That’s why planning is everything.
In this guide, you’ll learn how to choose the right location, set realistic goals, protect your calendar, and create a schedule that lets you stay focused without missing the magic around you.
Because when it comes to workations, strong intention goes a long way. S when you want to blend meaningful work with a meaningful break.
How to Plan a Productive Workcation
Summarize this article for me pleaseWhat Is a Workcation?
A workcation is a working vacation. Simple.
It’s a trip where you travel to a new location but continue working remotely. You’re not taking time off work, but you are changing your physical environment. Most people choose to go on workation to recharge their mental and emotional batteries while still staying productive.
Some questions to ask before you start packing 👇
- Do I have to be available for real-time calls, or can I work asynchronously?
- What are the top three deliverables I must complete during the trip?
- Are there any deadlines, launches, or reviews that require me to be hyper-available?
- Can I batch or automate some tasks before I leave?
- What time zone will I be working from?
Summarize this article for me pleaseWhy Consider a Workcation?
If the words ‘work’ and ‘vacation’ sound like opposite forces, you’re not wrong. But then can be combined, as many workers do.
🧐 Did you know? Nearly 67% of workers in the technology industry work remotely! That’s the highest share of any industry.
When blended right, a workcation gives you the best of both worlds—structure and freedom, deadlines and downtime.
A workcation is also a great opportunity to develop new skills, whether it’s learning a language or mastering time-blocking.
Here’s why this new travel trend might be exactly what you need:
- Fewer distractions: Surprisingly, being away can make it easier to focus. No office chatter, fewer random meetings, and no laundry piling up in your peripheral vision means more space for actual deep work
- Enhanced motivation: When you wake up somewhere exciting, even your morning to-do list feels different. The anticipation of exploring a new destination after work can give you that extra push to power through tasks efficiently
- Better balance: It’s easier to integrate wellness into your working world when you’re not locked into your usual job patterns. You might start your mornings with a hike, take breakfast outside, or wind down watching sunsets, all while keeping your projects moving
- Flexible structure: Without the rigid 9-to-5, you can shape your workday around your energy levels—the biggest perk of workplace flexibility. If you’re most focused in the mornings, get the heavy lifting done early and enjoy your actual vacation in the later part of the day
- Fresh perspective: Physically stepping away helps you mentally zoom out. You might realize that the project requires you to look at it from a different angle or that a new direction is what your team needs to make it work. Some workers find their creativity skyrockets when their physical environment changes
- Intentional reset: For knowledge workers, workcations can help improve work-life balance, support mental health, and make remote work more fulfilling
- Retention and team morale: From a team leader’s perspective, encouraging workcations helps with employee retention. When employees feel trusted to work remotely and still hit their goals, they’re more likely to stay engaged and loyal. It shows that the company values work-life balance and mental health, not just output
🤝🏻 Friendly Reminder: Choosing a destination with reliable Wi-Fi and minimal distractions makes sense if your goal is to stay productive while enjoying a change of scenery.
Summarize this article for me pleaseHow to Plan a Successful Workcation?
If you want to get things done and unwind during the precious vacation days, you’ll need a plan for your workcation.
Here’s how to do it right:
1. Pick the right destination
At the workcation, you’re blending work with travel. That means thinking about:
- Reliable internet (not just speed, but consistency)
- Work-friendly spaces, like a desk, an ergonomic chair, or access to coworking areas
- Time-zone alignment if you’re syncing with a remote team
- Comfort and climate, especially if you’ll be on long calls or doing deep work
- Local amenities, like cafés, groceries, or even pharmacies
- Leisure options to balance work and productivity with play and leisure activities
A smart trick? Vet the destination like you would a new office. Browse reviews on platforms like Nomad List, Workfrom, or WiFi Tribe to get a sense of internet quality, digital nomad friendliness, and living costs.
Dive into Reddit threads, like r/digitalnomad, for firsthand experiences on remote work. Nothing derails focus faster than choppy Zoom calls or noisy neighbors when you’re trying to hit a deadline.
Once you’ve shortlisted a few options, compare, collaborate, and finalize with ClickUp, the everything app for work. One of its best solutions for this stage is ClickUp Docs.
You can:
- Capture ideas on the go: Let’s say you’re working from a beach café and a product idea hits you mid-sip. As a remote work tool, Docs lets you instantly jot it down and link it to a Task
- Collaborate seamlessly: Even in different time zones, when you work remotely, Docs lets you co-edit in real-time, assign action items directly from within the doc, and drop comments your team can act on, for hybrid collaboration
- Keep everything in one Workspace: Use Docs to manage both work and travel plans. Create a personal itinerary with tables for flight info, hotel bookings, and local spots. Add emojis, banners, color-codes, or embed external links to make it more fun and visual
💡 Pro Tip: Need to urgently align with a teammate while you’re on the move? Just open ClickUp Chat. Ping teammates, drop in a task link, and keep the convo focused without cluttering up your email.
2. Set clear work goals for the trip
One of the biggest mistakes people make on a workcation? Treating it like a regular workweek with a prettier view.
Without structure, your days can quickly blur into scattered to-do lists, half-finished tasks, and guilt for not doing more or enjoying the trip enough.
To avoid that spiral, set a few intentional goals before you leave. Ask yourself:
- What do I actually want to accomplish during this trip?
- Are these deep focus goals (e.g., writing a strategy doc) or day-to-day operations (e.g., client check-ins)?
- What are the must-do deliverables vs. nice-to-haves?
- How will I measure success—by output, hours, milestones, or something else?
Also, consider the rhythm of your days. You could block mornings for creative work and keep afternoons lighter for admin or exploration. ClickUp makes this easier with ClickUp Goals.
Each Goal is a container for progress you want to make. Inside that, you can set Targets like:
- Number-based (e.g., write three blogs)
- True/false (e.g., submitted client proposal?)
- Currency (e.g., close $5K in deals)
- Tasks completed (link tasks you’re already working on)
Each target can be linked to specific ClickUp Tasks with:
- Subtasks and checklists to manage complexity
- Due dates and priorities to help you stay on track without feeling overwhelmed
- Custom tags like ‘Deep Work,’ ‘Async,’ or ‘Calls’ to filter and plan your day intuitively
📚 Bonus Read: How To Keep Remote Employees Engaged & Productive
3. Design a flexible but focused daily schedule
A productive workcation is about designing a schedule that respects your energy, fits your surroundings, and makes room for both deep work and downtime.
Here’s what works:
✅ Pick one core work block (9-11 am for focused work) and one break or leisure window ( 4-6 pm for local exploring). These become your anchors. Everything else can flex around them
✅ Don’t just fill your calendar with hours. Think in modes:
- Deep work: Writing, strategy, or code
- Light work: Email, status updates
- Calls/collaboration: Meetings, reviews
- Recovery: Walks, food, naps
✅ Every evening, to save your time the next day, spend 5 minutes planning tomorrow. Set 1-2 top priorities, review your calendar, and clear away distractions
Use ClickUp’s time management tools to organize your workation:
- Turn your work blocks into ClickUp Time Estimates, so you don’t overbook yourself. ClickUp will show if you’re cramming 9 hours of work into a 4-hour window
- For accountability, use ClickUp Time Tracking to monitor how long each task takes and adjust your schedule based on the feasibility
📮 ClickUp Insight: 1 in 5 professionals spends 3+ hours daily just looking for files, messages, or additional context on their tasks. That’s nearly 40% of a full workweek wasted on something that should only take seconds!
ClickUp’s Connected Search unifies all your work—across tasks, docs, emails, and chats—so you can find exactly what you need when you need it without jumping between tools.
4. Automate what you can before you leave
Before you pack your bags, take some time to review your workflow and identify what can be automated.
Start by identifying tasks that:
- Repeat on a schedule (like sending status updates or weekly reports)
- Depend on clear triggers (‘when a task is marked done → notify the client’)
- Involve manual reminders (follow-ups, checklist items, or document updates)
Use ClickUp Automations at this point to build if-this-then-that workflows to handle the gruntwork for you.
When you’re running out of time, ask ClickUp Brain about what you have on your plate for the day.
In a nutshell, here’s how ClickUp Brain lets you be productive on your workcation:
- Instantly pull context from Docs, Tasks, and notes just by asking a question
- Auto-summarize project updates, so you don’t waste your morning catching up
- Generate ideas or outlines while you’re between deep work blocks
5. Centralize everything you’ll need remotely
You don’t realize how many little things you rely on until you’re somewhere new. A single missing file can waste hours when your Wi-Fi connection is unstable and no one in your team is online to help.
Before you leave, make a checklist of everything you’ll likely need access to:
- Important docs: Project briefs, SOPs, client info, contracts, and internal how-tos
- Assets: Templates, brand files, pitch decks, and design guidelines
- Context: Past meeting notes, performance dashboards, and workflows
- People: Who’s the go-to for each project, escalation contacts, and time zones
Then ask: Where is all this information? Is it easy for me to access without asking someone?
Centralize everything in one place before you leave. Create a go-to hub where your workflows, reference materials, and collaboration points are all connected and searchable.
And the best way to centralize your end-to-end workflow? ClickUp Knowledge Management!
Store and organize all your documents, wikis, and resources in one place. This centralized repository ensures you have access to all necessary information, regardless of your location.
During this time, use ClickUp’s Remote Team Solution to tie everything (and everyone) together. It connects your Docs, Tasks, Chat, and Goals into one unified space, so your team stays synced around the world.
Once your resources are centralized, use the ClickUp Remote Work Plan Template.
It helps you create a work plan by:
- Assign clear responsibilities by department, so everyone knows what they own
- Set expectations upfront using ClickUp Custom Fields like Deliverables, Goal, Allocated Budget, and Actual Cost
- Track real progress using ClickUp Custom Statuses like To Do, In Progress, Blocked, and Complete
ClickUp Views, like Work Activities, let you organize tasks by team (HR, Sales, and Marketing), while the Work Timeline shows how all the moving parts connect.
6. Don’t forget life beyond work
A successful workcation is all about being present. If all you do is move your to-do list to a new location, you’re missing the point. Build time into your schedule for what doesn’t look like work:
- Morning walks before your first call
- Exploring local food spots between tasks
- An hour to sit still, journal, or just enjoy where you are
Stepping away from your screen creates space for clarity, creativity, and energy you can’t fake through back-to-back meetings.
Don’t let these reflections get lost in your head. Use ClickUp Notepad—a quick, lightweight space where you can jot thoughts, travel ideas, or creative sparks that hit mid-breakfast.
Then, for your actual work life? Let ClickUp AI Notetaker handle the heavy lifting during meetings. It automatically captures key takeaways, action items, and decisions so you can stay present without scrambling to write everything down.
If you want to make life beyond work a little more organized, the ClickUp Business Travel Itinerary Template is your perfect companion for the business trip. This template helps you keep your travel plans, accommodations, and daily activities in one place when you work remotely.
At a glance:
- Store all your lodging details, like hotel name, address, room number, check-in/out times, so it’s right there when you arrive
- Plan your day-to-day schedule with space for date, time, place, activity, and notes. Whether it’s a coworking session, city tour, or client dinner, you’ll know exactly what’s next
- Log airport details, gate number, airline info, travel time, and confirmation codes (perfect for when you’re in transit and need quick access to everything)
Summarize this article for me pleaseChallenges of a Workcation (and How to Overcome Them)
While a workcation may sound like the perfect mix that combines work and vacation, there are some challenges you’ll need to keep in mind to ensure you’re able to unwind and maintain your work-life balance.
1. Difficulty setting boundaries
When you take a workcation, drawing a clear line between work and relaxation time can be difficult. Without the structure of an office, you might end up working late into the evening, which can lead to stress or guilt.
✅ Solution: Set specific work hours, like 9 AM to 5 PM, and stick to them every day of your remote work. Use tools like ClickUp Reminders to remind you when to start and stop working. For example, set a reminder 30 minutes before the end of your workday to start wrapping up tasks.
2. Unreliable technology and connectivity
Not every location offers the kind of reliable Wi-Fi or tech infrastructure you need to work smoothly with your hybrid schedule. If the internet is slow or unreliable, or if you lack a proper workspace, disruptions will throw off your schedule and cause frustration.
✅ Solution: When you’re choosing a place to stay in a new city, make sure the place has solid Wi-Fi. Look for keywords like ‘business-friendly’ or ‘dedicated workspace’ in the listing. If you’re booking an Airbnb, check the reviews to see if other guests mention internet speed.
📚 Read More: Unlocking the Future of Productivity With ClickUp
3. Time zone conflicts
If you’re in a different time zone during your workcation, real-time collaboration with your team means you will need to adjust your work hours to align with theirs. In other words, you may end up attending calls late at night or early in the morning.
✅ Solution: Set ‘core hours’ that work for you and your team, even if it’s just for brief check-ins during the working vacation. Use scheduling tools like ClickUp Calendar to adjust to your time zone automatically, so you don’t spend time figuring out when to meet.
4. Managing health and well-being
Adapting to new foods, water, or climate changes can affect your health and energy levels during the workcation. If you’re not careful with your diet or fitness routine, it might become harder to stay focused and productive. Keeping an eye on your health is crucial to maintaining your performance while on a workcation.
✅ Solution: If you’re in a place with different food or water, drink bottled water and avoid street food until you adjust. Pack snacks or supplements you rely on, like vitamins or protein bars.
Find a local gym or use fitness apps for home workouts, or take a 30-minute walk in the morning to start your day. If you’re in a hot or polluted area, schedule your outdoor activities for early morning or late evening.
Summarize this article for me pleaseTop Destinations for a Workcation
Based on user reviews from around the world, here’s a list of top destinations for your next workcation, where you can balance productivity with relaxation:
1. Bali, Indonesia
Bali gives you the perfect blend of work and relaxation for digital nomads. With a range of coworking spaces and lush tropical surroundings, you can get your tasks done while enjoying the island’s serene vibes in your free time.
💡 Pro Tip: To make the most of your Bali workcation experience, use a travel management software to centralize all your tasks. Create a clear itinerary, set reminders for key check-ins or visa deadlines, and keep everything accessible even when you’re on the move.
2. Lisbon, Portugal
Lisbon’s combination of modern coworking spaces and rich history makes it a great spot for a workcation. You’ll have a productive workday and can unwind with cultural experiences, fantastic food, and scenic views.
💡 Pro Tip: Use itinerary templates to get a comprehensive view of your trip, including lodging, events, restaurants, and a packing list. Some templates also allow collaboration, so you can share your plans with your team members and stay organized.
3. Tulum, Mexico
In Tulum, you can work in beachside coworking spaces and take breaks with yoga or beach walks. The laid-back vibe is perfect if you want to unwind while staying on top of your tasks.
💡 Pro Tip: If you’re an entrepreneur on a workcation in Tulum, use the Pomodoro Technique, involving 25-minute focused work intervals followed by short breaks. This productivity method is great for tackling tasks efficiently, then rewarding yourself with a brief walk along the beach or a quick swim.
4. Barcelona, Spain
Barcelona’s dynamic atmosphere attracts knowledge workers seeking workcation destinations. After your work hours, you can explore its stunning architecture, vibrant culture, and delicious cuisine.
💡 Pro Tip: On your workcation, use a digital nomad tool that offers cross-platform compatibility. Whether you’re using a laptop, tablet, or phone, the tool should sync seamlessly across devices.
5. Kyoto, Japan
Kyoto’s peaceful temples and gardens offer a quiet place for your workcation. You’ll be able to focus during the day and relax in one of Japan’s most tranquil settings in the evenings.
💡 Pro Tip: During your Kyoto workcation, block mornings for deep work in a quiet café, and spend your afternoons exploring temples or strolling along the Philosopher’s Path.
Here are real-life work-life balance examples to help you structure your day, without burning out or missing out.
6. Cape Town, South Africa
Remote work amid scenic backdrops is how knowledge workers describe Cape Town. It’s an ideal destination for your workcation, where you stay productive while you take advantage of its outdoor activities during your precious vacation days.
💡 Pro Tip: Use a productivity template during your workcation to map out both personal and professional goals in one place. You need to avoid overcommitting to one side and make space for what matters on both fronts.
7. Chiang Mai, Thailand
Chiang Mai is an affordable destination with great weather, plenty of coworking spaces, and a welcoming atmosphere. It’s a perfect place for staying productive without breaking the bank.
💡 Pro Tip: Budget-friendly workcation locations with reliable Wi-Fi, affordable coworking spaces, and a thriving digital nomad scene are the ideal places to experiment with location-flexible productivity.
Summarize this article for me pleaseBring Structure to Your Workcation with ClickUp
Planning a productive workcation means knowing your goals, respecting your energy, and designing each day to support your work and well-being.
While you work remotely, you need a system that helps you plan ahead, stay organized on the go, and keep your team in sync.
That’s where you need ClickUp.
It brings everything you need into one place—from Docs to plan your itinerary and store project details, to Tasks and Goals that help you break down what needs to get done. Time Tracking and Calendar let you stay realistic about your workload, while Reminders help you bring structure to your day.
When you’re managing multiple moving parts of a big project, Automations and ClickUp Brain help streamline repetitive tasks and give you clarity fast.
To bring structure to your workcation, sign up on ClickUp for free.
Everything you need to stay organized and get work done.
