Whilst still working my 9-5 (ish, god knows I’m a Consultant), I’ve had to learn how to become extremely strategic when it comes to planning my trips. With 15 actual vacation days, I need to optimize when I take my vacations and where I go. I get many questions about how I’ve managed to travel to 38 countries by 24, the majority while getting my Masters Degree and working full time.

There are some simple tactics worth mentioning, which will allow anyone to squeeze an extra few vacation days out of their year.

Coupling Vacation with Statutory Holidays

This is the most simple strategy in optimizing your vacation days for the year. Take advantage of Canada Day and Family Day if you live in Canada and go on a trip! Statutory holidays are a free vacation day for you and a chance to go travel! The best part of statutory holidays is that the rest of your family and friends are typically off (pending occupation and client deliverables, of course), and you can share the adventure with them!

Travelling over Christmas and New Years

This ties in closely to Coupling Vacation with Statutory Holidays, as typically offices are closed for Christmas, Boxing Day, and New Years! If you’re lucky like I was the past year, your office will also give you a couple free days off. Travelling during this time can definitely be chaotic and expensive, but don’t let that scare you!

Here’s some tips for finding cheaper holiday travel:

  • Sign up for flight watchers early. I like to use Skyscanner and Hopper. Monitoring prices in advance allows you to see what price they typically are, and you’ll be alerted when flights go on sale!
  • Pick a non-typical travel destination! You can imagine resorts become quite expensive during the holiday season with vacationers trying to flee from the cold. If you’re looking for a beach vacation, pick an alternative destination such as Nicaragua or California!
Big Corn Island, Nicaragua in DECEMBER
  • Travel with friends. I highly recommend spending some time travelling alone, but bringing a travel partner (or two!) over the holidays will definitely bring down the cost of hotels.
  • Stay in accommodations with free breakfast, and/ or access to a kitchen. Eating whilst travelling can be expensive, but it doesn’t have to be! Pick up some sandwich materials or pasta from the grocery store and you’ll save a lot of money on food.

Work Remotely

This one heavily depends on your working arrangement. If you’re lucky, you may be able to work something out with your boss where you work remotely from a different area while travelling. This isn’t for everyone – it can be exhausting. But, if you plan out your days efficiently, you will be able to explore during the morning and the night! I love this approach as I really enjoy the feeling of being somewhere different, whether it involves exploring all day, or finding a nice coffee shop to do some work!

Plan Strategic Routes

I may have a bit of OCD when it comes to planning out my trips, but I am always keen on squeezing everything I can out of a trip, no matter how short. If I am away for two weeks or less, I tend to create a very thorough spreadsheet with colour coded itineraries. This may sound intense, but I find myself becoming increasingly more excited as I plan out my days, knowing I am going to be able to do the majority of things I want to. Of course, there are days where it will fall off track and you will have to improvise. But, that’s part of the excitement of travelling – you never know what’s going to happen! I’ll write more about my crazy trip scheduling in a future post.

Take Many Short-Haul Trips

I’ve been taking more short-haul trips lately – 1-2 days off around a weekend and travelling somewhere with a distance of about 5 hours or less from Toronto. With my experience, it is definitely easier to get a couple days of vacation approved compared to extended vacations. I’ve flown to Las Vegas, Iceland, New York, Chicago, Boston, Ottawa, Montreal, and many more on 3 or 4 day weekends! Of course, this isn’t enough time to explore cities in-depth, but a great chance to explore the highlights.

Adventures on a Four Night Trip to Iceland

Take a Sabbatical or Other Unpaid Leave

Craving a life changing experience? Feeling lost in your career or life? Want to see more of the world? A sabbatical or other unpaid leave may be of interest to you. This is not an option at every workplace, but I’ve found that a lot of companies do offer such programs. I’ve personally been debating if I should take some time off and explore the world while volunteering at various charities!

Somewhere over the Andes

Do you work full-time? What are some ways that you make the most out of your vacation days? Let me know in the comments!

Posted by:deventuretime

4 replies on “How to Travel More When You Work a 9-5

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