Dying to get away, but just can’t break completely free of work? Consider these winning ways to structure a working vacation.


I’ve gone on record before about the need for a standing desk and how to build one. Getting your work done from a standing position while traveling though is a different story, particularly when a desk and rolling chair are all you find available in your hotel room. How can I work around this, you ask? Consider checking email while standing at the bar for happy hour, or making an impromptu upright desk out of the bureau or counter top in your room.

Internet Access:

People-BeachLaptopWhen it comes to frugal essentials for business travelers, Wi-Fi makes my short list every time. With so many hotels offering this service as a complimentary amenity, there’s really no reason to spend extra anymore, unless you’re stuck at a not-your-choice venue due to a flight delay or cancellation. Most resorts have internet access outside as well, making a pool cabana a great place to keep in touch with work for emergencies while still having some lounge time with your boo.


It’s tempting to hit the spa for the whole week, I know. That being said, it’s a good idea to build in a little activity if can. Running a marathon isn’t your speed? No worries. There are plenty of world-class walking tours around the globe, allowing you to stroll and see the sites. As long as you’re up and moving, nobody can call you lazy. Walking tours can also be scheduled in between work sessions, where a full day on the mountain pretty much eats up any productivity you may have been able to achieve.


Some careers blend easily into a travel getaway, providing the opportunity to be productive while seeing the sites. One example is travel photography, but writing is another way to go, especially for those who write guide books for a living.


Whether your vacation atmosphere comes in the form of a sweeping view from the porch of your cabin or in the form of a romantic historical inn, it’s important not to go someplace dumpy. The point is to feel like you’re getting away from it all, at least for part of your stay. Choosing a dowdy and depressing hotel room is depressing, and you run the risk of wishing you’d never spent the money in the first place.

Time Management:

If you’re smart about how you choose to use your down time, you may end up with more time for fun than you think. For example, if you have a few productive ways to kill time before a flight up your sleeve, making time for that dinner luau just might be possible. Getting to bed early may mean you can check email and file reports between four in the morning and nine o’clock. If so, that will leave you with plenty of time to go site seeing for the day while still being able to deal with a couple of light projects again that same evening.

Having a working vacation is possible, provided you have access to the proper resources and manage your time accordingly. Do you take working vacations on a regular basis? What are your top tips for success?

Myscha Theriault

Myscha Theriault

A lifelong money cruncher who can squeeze a nickel ‘til it cries, Myscha is a syndicated columnist, best-selling author, and founder of Trek Hound and We Be Sharin’.