As marketers, all we need is a good wifi connection and a computer to get our work done. In our field, it is quite common to go on workations, and most people expect to have this flexibility if they sign a contract with a marketing agency. Workation is even more fun and enjoyable when your partner's job has the same flexibility. It has allowed us to travel more during the year without having to use our PTO. Our last workation was in Mexico. There are a few rules we had set in place to make sure we get the job done while having a great experience exploring the country. First: connectivity is non-negotiable. We always research in advance about the location we are looking into for our workation. For instance, in Mexico we chose Sayulita as one of our destinations because it is quite well known in the digital nomad community, so we knew in advance that there wouldn't be any issues with finding connections when there is the infrastructure for this kind of lifestyle. Second: time zones rule everything. We keep multiple world clocks on our phones and align our schedules to match. That means starting our workday at 5:00 a.m., giving us an overlap with clients who are seven or eight hours ahead. By 2:00 p.m., we close our laptops, and the rest of the day is for exploring. The top tip we'd give? Build a rhythm you can repeat, no matter where you are. Our productivity and project management thrive on consistency. Without it, we wouldn't be able to serve our clients properly. It is important to keep the same quality of work you would have in an office because otherwise it might be more difficult to ask your boss for workation the next time you want to go somewhere.
In 2021, I spent a month living in Oaxaca while continuing to work remotely. I coordinated closely with my clients and business partner during that time, and since Oaxaca was only two hours ahead of my usual time zone, I was able to attend most meetings without disruption. We adjusted our meeting schedule slightly to fit both of our time zones. My husband and I stayed at an art residency and had a local guide to help us explore the area. Our routine balanced work and travel--we worked in the mornings, explored in the afternoons, and logged back on in the evenings. During our day trips, we connected with local artisans, visited small boutiques, went mezcal tasting, and experienced the rich creative culture of the region. These moments added so much meaning to the trip and gave us a deeper appreciation for the local community. Clear communication with our teams made it easy to plan around travel days, especially when we needed to take a Friday or Monday off. That experience really showed me how well remote work can integrate with travel when there's strong communication and structure. Building on that, I'm actually taking off again this October for a year abroad. I'll be working remotely from a different country each month, continuing to support my clients while immersing myself in new cultures. I'm excited to bring that same focus, flexibility, and curiosity into this next chapter.
Time Management and Productivity Coach at Alexis Haselberger Coaching and Consulting, Inc
Answered 6 months ago
I have done MANY workcations over the last several years. (I own a time management, productivity and stress reduction coaching and consulting business. I've worked with hundreds of individuals to help improve productivity and decrease stress, I've taught 200,00+ people to do the same through my online courses, and my corporate clients include Google, Lyft, CapitalOne and many more.) 1. Where you went and for how long While I live in San Francisco, over the last 5 years, I've taken workcations. These trips have been from a few weeks at the lower end (Seattle, Vancouver, Palm Springs and Mexico City), to several months at the high end (Taipei, Seoul and Barcelona). 2. How you made it work with your team or clients I have a small team of contractors who are global anyway, so we are used to working completely asynchronously. No change needed there. As for my clients, because I coach over Zoom, the way I've made it work is to adjust my work schedule to a US timezone, where most of my clients are. When I was Taipei and Seoul, this meant that I completely altered my schedule; I slept from 4pm to midnight, worked from midnight to 8am and then explored and lived my life from 8am to 4pm, expect on weekends where I shifted my hours a bit so as to be able to eat dinner at a normal time and explore restaurants. In Barcelona, I worked "East Coast Hours", meaning that my sleep schedule didn't need to change much, but that I worked from around 3pm to 11pm each day and then explored in the morning and early afternoon. When I've been in places like other US cities, or Vancouver/Mexico City, which are on similar timezones, honestly not much changed at all for my clients and my workday, from a schedule perspective. The interesting thing is that, in the age of laptops and Zoom, most of my clients weren't even aware I was anywhere other than San Francisco; it simply didn't matter because it didn't affect the work. 3. Your top tip for balancing productivity with exploration My top tip is to define a clear work schedule for yourself, and make sure that it's reflected on your calendar. If you're using Calendly, or another scheduling tool, make sure it aligns with the hours you plan to work. If you're shifting your sleep schedule, make a plan (melatonin, sleep masks and daylight lamps, etc.). If there are things you want to do that don't fit the schedule, then make exceptions, but adjust your calendar early so that there's minimal impact on your clients/team.
As CEO of iHost, I've transformed "workcations" into a core business research approach. My most productive was a 2-month stay in Napa Valley where I tested our AI-driven property management systems while experiencing our corporate housing firsthand. This dual-purpose trip allowed me to identify inefficiencies in our guest expetience automation that weren't visible from headquarters. I managed remotely by dedicating mornings to operations and strategic calls, using our predictive analytics dashboard to monitor portfolio performance across markets. Afternoons were spent visiting competitors' properties and meeting with insurance housing partners to develop our specialized accommodations for displaced families. My top productivity tip: Use location-specific automation to create boundaries. Our smart home systems allowed me to program "work mode" lighting scenes and temperature settings that helped maintain focus during business hours, while automatically transitioning to "explore mode" at designated times - a feature we now build into all iHost properties for business travelers. The most valuable insight came from experiencing our own insurance housing product during California's wildfire season. Living alongside displaced families showed me which amenities mattered most during stressful relocations, leading us to redesign our insurance housing offerings with trauma-informed features like improved privacy controls and simplified check-in procedures.
I made a brave decision and exchanged Dubai's towering skylines for the dramatic landscapes of Canada and worked remotely for three months immersing myself in a very different pace of life. Working as a holiday planner means I have the ability to plan dream vacations for people all the time, but this time I was determined to plan one for myself—a workcation that incorporated work obligations into the mix of adventure. Scheduling clients from different time zones called for careful planning. I established regular hours that coincided with Dubai's workday for seamless communication. I also relied on automated scheduling platforms and pre-arrival check-ins, so they didn't feel the distance. The surprising twist? Most appreciated the fact that I was venturing into new places as this provided new ideas and suggestions into my travel recommendations for them. The secret to getting work and exploration balanced is scheduling the days like a itinerary. Similar to the way I book travel for clients, I planned work sessions and exploratory blocks. Rather than holding out for downtime to magically show up, I scheduled it in—with morning hikes before email time or shutting down for sunsets. By scheduling exploration as a non-negotiable part of the day, I remained productive while soaking up the wonder of work travel.
I've been fortunate to take several workcations — and to help make them accessible for my team as well. Getting the balance right is essential; it takes the right personality, in the right role, to make it sustainable. Two destinations where I've successfully combined work and exploration are South Africa and Mauritius. I spent about a month in Mauritius and often visit Cape Town for stretches of up to two months. The key to making it work is discipline — both with work and with play. You need to be realistic about whether your role can be performed effectively from your new location. For example, South Africa is just a one-hour time difference from the UK, where I'm normally based. This minimal shift made it easy to maintain my regular schedule. Mauritius was a 4hr difference while I was there - which made it more challenging as I'm often working with clients on PST. My top tips for balancing productivity with exploration: 1. Front-load the trip with vacation time. Spend the first few days purely settling in and enjoying your new environment. Once you feel at home, it's much easier to build a productive work routine. 2. Choose a sensible base. Strong Wi-Fi, a distraction-free environment for calls and meetings, and even a temporary co-working space can make a huge difference. 3. Be honest about your role's demands. If you're employed by a company, it's your responsibility to maintain your usual performance standards — remote or not. Self-employed travelers might have more flexibility, but salaried employees need to ensure their arrangements make business sense too. At my company, The Travel Whisperer, we have a formal policy allowing employees to work from different locations, provided they make sensible, realistic plans. Being in the travel industry certainly helps! Thanks!
From my personal experience, I once took a workcation in Lisbon, Portugal for a month. For a professional client in the indie music scene, we utilized digital tools like Google Workspace and Slack to effectively coordinate. My top tip for balancing work and exploration is to keep a strict schedule. I always made sure to complete my work during the mornings so that I could explore the city in the afternoons. From my point of view, discipline is the key to a successful workcation.
Hi! Absolutely love this topic - here are my answers: 1. Several places, but some standouts were London, Mallorca, Bogota 2. Clients were not affected, while they knew I was traveling, I was still connected and fully reachable, and if anything, I had renewed energy and inspiration and brought new ideas to the table. With wi-fi and global co-working spaces (including hotel lobbies, of course), it's so easy to be physically and virtually everywhere. 3. One of the most important things for balancing a workcation is time blocking - if you're in the EU and working with a team or client in the US, realize you are the one who needs to accommodate and dial into work at your client/team's local time zone. Schedule outgoing messages so they are sent at local times, not at 2AM PST, for example. It might make for some odd hours, but it's a worthwhile trade off to be out seeing the world and still being respectful of clients and teammates schedules. Arguably the biggest and most important currencies we have in our life is time - being able to responsibly work while managing where we are in our day to day life is the greatest gift.
Every summer, I take a workcation and spend several weeks working remotely from Europe--usually Italy where my husband is from. It's become a core part of my annual rhythm, both personally and professionally. What's unique about working abroad is that the time difference actually works in my favor. My mornings and early afternoons are completely free, which gives me the opportunity to be present with my family, enjoy slower mornings, and take in new experiences without sacrificing my workload. I typically structure my week into three half-days and one to two full workdays. On half-days, I'll log on around 3 PM local time and work into the early evening, often from a coworking space or hotel lobby that has a strong Wi-Fi connection and a quiet corner. On my full days, I will work through the day then pop out for a dinner and come back online after 11 pm, I stay up later to overlap more intentionally with my U.S.-based team and clients, reserving those days for client calls and live collaboration. The key to making this setup sustainable is overcommunication and planning. Before I leave, I align with my team on project timelines, designate point people for anything time-sensitive, and set clear expectations around my working hours. We hold internal team huddles every Monday and Friday to keep priorities tight and momentum high. Client meetings are stacked on my late-night days, so I can maintain responsiveness without compromising the flow of the week. What I love most about workcations is the mental reset they offer. Being in a different environment breaks the routine and sparks a new level of creativity. I find myself more inspired, more energized, and often returning with fresh ideas I wouldn't have uncovered in my normal day-to-day. It's also a rare chance to disconnect from office culture--physically and mentally--and evaluate what's truly productive versus performative. My top tip for anyone considering a workcation is to treat it like a mini business plan. Structure your calendar intentionally. Know when you'll be "on" and when you'll be exploring. Communicate clearly with your team and clients in advance. And choose locations with reliable infrastructure--because nothing kills a workcation vibe like bad Wi-Fi. Done right, a workcation doesn't take away from your output--it enhances it. For me, it's the ultimate blend of freedom, focus, and inspiration.
Since the start of the pandemic, I've embraced remote work from destinations around the world. Although based in Texas and working Central Standard Time hours, I've successfully completed workcations in the UK, Jamaica, Japan, the Philippines, and several U.S. states. Most trips ranged from one to two weeks, but my time in Japan extended to a full month. The key to making it sustainable was transparency. I proactively informed my team about my location and time difference to avoid any surprises during meetings or calls. I also communicated with clients as needed and remained committed to working CST hours—sometimes requiring late-night or overnight shifts. Tools like scheduled email sending and flexible project management platforms made maintaining normal operations seamless. My top advice for anyone considering a workcation is to be brutally honest with yourself about your work habits. If you can truly deliver the same level of focus and quality after a day of exploring a new city or country, then the experience can be incredibly rewarding. However, if you're unsure whether you can self-motivate under those circumstances, it may be better to wait until you are more confident in your ability to balance both. Logistics are equally important: always prioritize accommodations with reliable Wi-Fi and dedicated workspaces. If you're traveling with family or friends, create clear physical boundaries between your work zone and their leisure spaces to maintain both productivity and harmony. And finally, schedule at least one or two true vacation days during the trip to fully disconnect and enjoy your surroundings—after all, the experience should be just as rejuvenating as it is productive.
I just wrapped up what I'd call a dream setup - nearly two months in China visiting family while keeping my full stack developer job at Penfriend AI going strong from 5,000 miles away. My Vancouver team and I hammered out when I'd be online despite the crazy time difference, and they cared more about my actual work than watching me clock in at specific hours. Some days I was coding at midnight with a cup of tea while my team was just starting their morning coffee! What really saved me was drawing a hard line between work and play. When I was "off," I was truly disconnected, exploring local markets or catching up with relatives I hadn't seen in years. I got smart about my schedule too, putting in longer hours early in the week so I could enjoy three-day weekends exploring the countryside with family. Having my own little workspace corner at my parents' home made all the difference. My family knew that when the headphones went on, I was in "Vancouver mode." The whole experience taught me that with some upfront planning and mutual trust, you can absolutely have the best of both worlds.
Took a six-week workcation in Lisbon. Biggest win: I aligned my hours with my team's timezone before booking anything. Even though Portugal is 5-8 hours ahead of most U.S. teams, I structured my day: mornings for exploration, afternoons and evenings for deep work and meetings. No friction, no weird explanations. Key move was booking an apartment with rock-solid internet and a proper desk. Airbnbs often lie — I asked for a real-time speed test screenshot from the host before confirming. Saved me from scrambling at the last minute. Top tip: treat the trip like a split-shift job. Set non-negotiable work blocks, and protect them harder than you would at home. You'll explore more guilt-free because you know your work's locked down. Winging it sounds romantic but kills both work and fun.
I've been working remotely while traveling for years, and it's completely transformed my perspective on work-life integration. I started with a three-month stint in Bali, then spent four months across Portugal and Spain, followed by shorter stays in Colombia and Mexico. Making it work with my team required intentional communication. I maintained overlap with core business hours by shifting my schedule—sometimes working early mornings or late evenings—and I was transparent about my availability in our shared calendars. Weekly video check-ins became non-negotiable touchpoints, and I made sure to overcommunicate on Slack about my progress and any potential connectivity issues. My top tip? Establish a consistent morning routine, regardless of location. I dedicate the first three hours of each day to focused work before any exploration. This creates a psychological foundation for productivity and gives me the freedom to explore in the afternoons without guilt. I've found that I'm actually more productive in shorter, more focused bursts than I ever was working traditional hours in an office. The key is being disciplined about when you work, so you can be fully present when you play.
I've been running my short-term rental business while traveling between Detroit and New Orleans for the past several years. My longest workcation was a 6-week stay in New Orleans where I managed our Detroit properties remotely while exploring my wife's hometown and building business connections in both cities. Making it work with clients meant setting up systems beforehand. I created detailed guest guides with local recommendations, installed smart locks for remote check-ins, and partnered with reliable cleaning crews in Detroit. The time difference actually worked in my favor—I could handle Detroit morning check-outs while enjoying my coffee in New Orleans. My top tip is to leverage your dual location as a business advantage. While in New Orleans, I studied their hospitality touches and implemented them in our Detroit properties. This cross-pollination of ideas (like adding local coffee and personalized welcome notes) significantly improved our guest ratings from 4.7 to 4.9 stars. The travel industry experience from my limousine and hospitality background helped me understand what travelers truly value. Instead of viewing my workcation as time away from business, I used it to gain competitive insights that made our properties stand out in Detroit's growing short-term rental market.
I embraced what I call the "Southeast Asia Circuit" for my workcation adventures: Location & Duration: I spent three months working across Southeast Asia's most vibrant, up-and-coming digital nomad hubs: Ubud, Bali: 4 weeks immersed in wellness-focused co-working spaces among the rice fields Chiang Mai, Thailand: 4 weeks in a community-driven coworking cafe environment Ho Chi Minh City, Vietnam: 4 weeks blending fast-paced business culture with dynamic city life Making It Work: What made this workcation effective was syncing my workflow with each location's rhythm and leveraging local advantages: Time Zones: Southeast Asia's time zone let me overlap with both US and European clients--it turned late evenings into prime meeting slots. Community Integration: I joined local business events and digital nomad meetups, instantly expanding my professional network and gaining access to insider knowledge (best WIFI spots, legal/business tips, local designers for quick freelance projects). Tech Readiness: I relied exclusively on portable tech--laptop, a Wifi hotspot, and cloud-based tools--so I could set up my "office" effortlessly in a beach cafe, jungle coworking loft, or bustling city lounge. Top Tip - "Three Layers Method": Layer 1: Dedicated work blocks in distraction-free coworking spaces (often with daily or weekly passes, or bundled with wellness perks like yoga/meditation in Ubud). Layer 2: Midday cultural "sprints"--I scheduled lunch breaks as mini-adventures: a temple visit, street food crawl, or local market stroll. Layer 3: Social hour every evening--whether a group hike in Bali, cooking class in Chiang Mai, or rooftop networking in Ho Chi Minh City--both for genuine downtime and local business leads. Takeaway: In Southeast Asia, workcations become sustainable when you intentionally blend productivity, culture, and community. The real magic? Your "office" may have a different view every week, but plugging into local ecosystems leaves a lasting business impact.
Excited about this piece -- I'm Gigi Robinson, a digital entrepreneur, speaker, and founder of Hosts of Influence. As a creator who also runs multiple businesses (@itsgigirobinson social partnerships, speaking, books, and @itsmrzeke social partnerships), I've fully embraced the "workcation" lifestyle and have a few great examples to share: I recently worked remotely from Delray Beach, FL for two weeks and earlier this year did a two-week trip through Ireland, where I balanced content creation, brand partnerships, and digital meetings while on the go. This summer I am headed to Israel for a workaction focused on creative entrepreneurship and networking. I made it work by over-communicating with my team and clients. I used shared Google calendars, meets for async check-ins, and Notion to keep everyone aligned. I also batch-scheduled content before traveling and blocked off hours for focused work vs. exploring. It's all about structure with flexibility. My biggest tip? Pick a few "anchor hours" every day where you're reliably online, then plan around that. And don't overbook yourself -- leave space to be inspired by your environment, especially if creativity is part of your work. Your brain needs downtime, too! Happy to expand or provide photos if helpful. Thanks for considering my POV! Gigi Robinson 7187448319
Founder & Chief Executive Officer, Nepal Hiking Team at Nepal Hiking Team
Answered 6 months ago
A few years back, I found myself working from the serene mountain town of Pokhara in Nepal for a month. Being surrounded by nature, yet having access to decent internet, was a real treat. The key to making this work was establishing a clear communication schedule with my team—early morning check-ins before trekking up the nearby trails and responding to emails during the quiet evenings. This routine ensured that I was both productive and responsive to any urgent matters. Make time-blocking your best friend. Allocate specific hours for work and separate times for exploration. This requires honest self-assessment: know when you're at your most productive and plan accordingly. For example, if you're sharper in the morning, tackle your hard tasks then, leaving afternoons or evenings for local adventures. Importantly, this structure not only keeps you on track with tasks but also allows for guilt-free exploration since work commitments are already fulfilled.
As the CEO of Jon Thomas Consulting, a 2x Inc. 5000 fastest growing company with clients around the world, I'm on the road (or in the air) about eight months out of the year. Last year led to me being on 6 continents in only 6 weeks. With such a global footprint, workcations are far more of a lifestyle than a trend for me. Where I went and for how long: I've worked everywhere from coffee shops in Cairo to coworking spaces in Mumbai. One of the most memorable was a multi-week trip to Kenya, where I visited a remote medical clinic I help lead in the Masai Mara. Beautiful as it was, this was the only time my workcation plan nearly unraveled — intermittent Wi-Fi eventually prompted a client to (politely) ask, "Where are you?" How I made it work: My approach to working remotely while traveling revolves around preparation and consistency. I schedule flights around standing meetings, always confirm Wi-Fi strength in advance, and keep multiple connectivity backups (local SIMs, hotspot devices, etc.). I also structure deliverables around predictable checkpoints, so clients continue to feel supported — ideally without even realizing I'm halfway around the world. Top tip for balancing productivity with exploration: Overcommunicate and overprepare. Set expectations clearly, both with your team and yourself. That, and make use of time zone differences — I often finish core deliverables by lunch and explore in the afternoon. Truthfully, I get more done while traveling than I ever did in a traditional office — fewer interruptions, more inspiration, and none of the burnout that comes from staring at the same four walls. My personal philosophy is that clients should always feel like they're getting the same (or better) service, no matter where I am. The reality is: while deliverables never slip, travel can look like you're doing less — even if you're twice as productive without the distractions and stagnation of a stuffy office.
I've lived the workcation lifestyle across five continents - Costa Rica, Southeast Asia, the Middle East, Colombia, the list goes on. My #1 secret is booking coworking spaces in every location. They're absolute lifesavers, especially if your calendar is booked with video calls. While many Airbnbs and hostels advertise "remote work friendly" listings, the WiFi is rarely as reliable as promised, especially in less connected countries. Coworking spaces deliver dependable connections because, well, reliable WiFi and a quiet space to work is literally their business model. The second game-changer was setting stricter parameters for my availability. I established clear meeting windows that worked across time zones, then communicated these boundaries upfront with my clients. Surprisingly, clients were incredibly receptive! Turns out, no one actually wants to interrupt someone's adventure abroad (even if you are working). But, even with a coworking space and predetermined "meeting hours", things will happen. Wifi will go out in the entire city, your coworking space will close for a holiday you've never heard of, and you'll forget your power adapter in the hotel. Embrace the uncertainty.
1. Where you went and for how long I spent four weeks working remotely from Bucharest a couple of years ago, traveling, visiting relatives, and working full-time. 2. How you made it work with your team or clients I've done workcations before, but this one was a little tougher because Bucharest is seven hours ahead of my regular time zone. Fortunately, I have a great team dynamic and was able to get by with mostly asynchronous communications with a few meetings and synchronous chats mixed in. My workday essentially flipped, and I'd often start work around 2 PM Bucharest time and continue into the evening to get a decent window of overlap with my team for necessary live syncs. I made it clear they had the green light to handle routine operational hiccups or approve standard marketing content drafts without needing my sign-off when it was the middle of the night for me. All non-urgent updates, questions, and feedback happened via detailed written messages, project management tools, or pre-recorded video messages on Loom. Any crucial client calls absolutely had to be locked into calendars weeks in advance, coordinating carefully to find slots that respected both their normal business hours. 3. Your top tip for balancing productivity with exploration Stay longer if you have to work full-time. Workcations and even digital nomadism can be the ultimate failure of multitasking if you try to take on too much or move around too quickly. When people often start out trying to find balance, they change locations quickly, but that means a lot less time to spend exploring or working, and a big chunk of time gets eaten up by the logistics of travel. Instead of trying to 'do' three major European cities in three weeks while working full Canadian/US hours, pick one city - maybe spend three weeks just in Lisbon, or a month based in Vancouver. When you can't get away with working less, extend the timeline horizon so you still get to see the things you want to and have enough downtime to avoid exhausting yourself.