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Business Meets Pleasure: A Guide to Working While on Vacation

Vacations are amazing, but did you know that working vacations can be incredible experiences, too? It can be hard to completely separate yourself from your work for the time it takes to get a really good vacation in, but there are ways you can relax and have fun while keeping up on your workload.

Take Advantage of Downtime

Before you hit the beach, consider this: Is there a point in the year where your workload is less? Even if you can’t get away from it all without working, you may be able to take advantage of a natural downswing in work so you don’t have to worry about fitting everything in while you’re away. Once you’ve narrowed down a possible month or two, compare it to the best times to travel to the location of your choice.

Designate & Delegate

Before you leave, designate another person to be your in-office point of contact. This can be the individual who you correspond with directly, which can eliminate in multiple texts, phone calls and video conferences with everyone in the office (which, as you can imagine, can be stressful and confusing). In addition, make sure that some of your daily tasks, specifically ones where being present is a must, are taken care of by other people in the business. This makes it possible for you to go on vacation in the first place — and it alleviates some of your workload as well.


Working vacations are all about work, of course, but they are also all about vacations, too. Schedule your time just like you do when you’re at home on the job. Set up times for work and times for relaxation or vacation activities — and stick to that self-imposed schedule. Better yet? One pleasant feature of a working vacation is that you may be able to be pretty flexible — have a massage scheduled for 10 a.m.? Shuffle your work to a later time slot.

Choose an Amazing Spot

Some locales are ideal for working vacations. Envision yourself at a place like the Blue Osa Yoga Retreat in Costa Rica. With its incredible climate, the fact that it’s located right on the beach and the bonus that WiFi is available, it’s a no-brainer for someone who wants to have a really fulfilling working vacation while relaxing to the fullest.

Stay Connected & Secure

Some amazing prime vacation locations can be pretty remote. Fortunately, modern technology makes staying connected far easier than ever before. Use apps like WhatsApp and Viber to text and call from abroad. With wireless Internet readily available, you can get your devices online from almost anywhere. Be careful of connections that aren’t secure as you put your computer in jeopardy of spyware and malware. If you are unsure about the security of the connection, don’t put your personal or financial information at risk.

Own Your Working Vacation

While it can be kind of a drag to work while you’re supposed to be on vacation, make it a point to own it. Don’t sit around and be discouraged or stressed out that you have to work later — do it earlier in the day so you can enjoy the rest of your day, or push work that still needs to be done to the back of your mind as you enjoy your yoga session. Not everyone can take a working vacation in the first place, so it’s an excellent idea to keep positive and get what you can out of your stay while keeping connected back home. It really can be the best of both worlds.