How I Travelled to 8 Countries in 1 Year with Little Vacation Time

Jenny Shen
4 min readDec 25, 2014

In 2013, I travelled to 8 countries, 16 cities while working in Singapore full-time.

One weekend, I was enjoying delicious street food in Ho Chi Minh, in the next I was diving to see a ship wreck in Bali.

I’ve walked on the white sand beach (as seen in The Beach) in Ko Phi Phi Leh and I’ve danced in Stereosonic, a two-day outdoor festival in Perth.

I’ve spent a weekend in Kuala Lumpur attending UX Malaysia to gain more UX knowledge, and a week in Bangkok pitching our startup at iStart Thailand.

The complete list: Bangkok, Hua Hin, Phuket, Phi Phi, Ko Samui, Ko Tao, Ko Phangan, Ho Chi Minh, Bali, Kuala Lumpur, Penang, Johor Bahru, Manila, Perth, Vancouver and Taipei.

The surprising part of this was that I didn’t have 6 weeks of vacation — only 12 days.

This is how I travelled with little vacation time:

Utilize public holidays

First, find out the public holidays for the year. E.g. Singapore’s 2014 Public Holidays

When you find a flight sale, look up the next convenient date and combine it with a weekend to maximize your holiday. For example, if a vacation falls on a Tuesday, you only have to take Monday off to enjoy a 4-day vacation (Saturday to Tuesday).

For an itinerary like this, I usually leave work early on Friday to fly out Friday evening or Saturday morning, and return on either Tuesday late night or Wednesday early morning. For Bali I actually did a weekend trip without any public holidays (Friday evening to Monday morning)

It sounds a bit tough, but with some redbull/coffee and a strong willpower you will be able to make it through the trip (and the day at work when you come back).

Pack your schedule

1 city and 4 islands, how much time would you need? What usually takes 2–3 weeks to visit, I did it in only 5 days. With a return to/from Phuket, I also went to Ko Phi Phi, Ko Samui, Ko Phangan and Ko Tao. Basically I was in a different place almost every day. In one day I went from Ko Samui to Ko Tao to Ko Phangan.

It’s not the best travel style for some people, but I like visiting many places at once. Some people can take 1 month to see the places I went to, but in reality, even if you stay for a week, you will want to stay longer. With these impressions, I can always go back to my favourite places in the future.

But be careful not to overpack the schedule (or oversleep)! In Ko Phangan I was an inch close to missing my ferry to Samui which would have led to missing the flight to Phuket. I woke up one hour before the ferry departed while I was still up in the mountains, miles away from the pier…

Perth, Hua Hin, Ko Phi Phi and Taipei

Unpaid leave

If taking one or two days unpaid leave won’t make you starve, it’s good idea to extend your vacation.

For the places I wished to go and enjoy for a longer period, like Taipei, I took 3 days of unpaid leave, combined with a public holiday and 5 days of annual leave to get 2 weeks of travel time. It was really worth it because I would have loved to stay even longer.

Work extra hours

To make up for the time I missed at work for travelling, I did extra work in the evenings, late nights or weekends.

Depending on how much flexibility there is in your work hours and how it might affect your colleagues, you could bank or make up hours by working an hour more daily for a few days, or work during a weekend.

Work remotely

Being able to work remotely is one of the advantages being in the IT industry. I was able to do work when I went back home for 2 weeks in Vancouver.

If you can do your work with a laptop and internet connection, such as programming, translating, copywriting, designing and marketing, encourage your company to allow you to work remotely.

I recommend reading 37signals’ Remote. 37signals is an inspiring IT company with a remote workforce spread out across nearly 30 cities across the world.

Consider a career change

Besides working remotely, there are options with more flexibility to travel. For example, online business owners, flight attendants, pilots, sales agents, writers and photographers either travel for work or have flexible work schedules.

Of course, you may not be a single 20-something ready to drop everything and become a nomad today. But you could start by taking up remote work on the side. Perhaps you have a skill you could teach online in your spare time — be it cooking, languages, or handcrafting. Or you could take an online course to learn a skill which could help you find remote work.

Becoming a freelancer or a remote worker could require a career change, a mental and lifestyle shift. It takes some time to research what it takes and to ease yourself into freelancing.

I plan to write about being a freelancer in another blog post. In the meantime, you could use public holidays, unpaid leaves, banked hours and a packed itinerary to get the most out of your vacation days.

Let’s stop saying “I have to work! I don’t have enough vacation! I’m too busy!” and see more of the world.

Follow my nomad adventure and get more travel tips on Twitter and Instagram.

Jenny Shen

UX Consultant specializing in international growth strategy, localization and cross-cultural design. Hire me to grow your business! More info @