Tips & gadgets for an amazing, productive working holiday

by Chris Winfield-Blum  - June 26, 2024

Imagine conquering European adventures (Like we did in 2023 between July-October, amazing!) or travelling through Asia with your family while still crushing your work goals. The secret? Striking a balance between packing light, staying productive, and keeping everyone happy. Here are some tips and tricks to help you achieve just that!

🧳 Pack Like a Pro: 7 Days of Outfits, Endless Memories

Overpacking is a common travel trap, especially with a family. Resist the urge! Think about the climates and activities you'll be enjoying. Here's the key: pack light (1 luggage if possible!), no more than 7 days. Choose versatile pieces you can mix and match, and layer and don't forget the power of rolling your clothes and packing cubes to save space and keep organised.

Kids' clothes are a different story, of course! You do need to pack extra for messy pasta meals and icecream when travelling through Italy.

We packed light for our European adventure with 2 adults and 1 child! We managed with just one large suitcase, using a separate duffel for our portable car seat (essential for trips that include driving) which also doubled as an overflow bag for laundry and anything else.

🏨 Beyond Airbnb: Your Working Holiday Accommodation Guide

Finding the perfect accommodation is key for a working holiday. Don't just limit yourself to a single type of accommodation! Consider AirBnB, hotels, serviced apartments, and their unique (and recently much more balanced) value propositions. Think about factors like cost, laundry facilities (essential for light packers!), and location of course. Also remember, that trendy AirBnB might have hidden fees like a hefty cleaning charge – be sure to factor those in before booking.

I like to ensure that at a minimum I have an AirBnb or serviced apartment with a washing machine every other week to keep us looking good and smelling great.

🤷‍♂️ Work-Life Harmony on the Road: Setting Family Expectations

Clear communication is crucial for a successful working holiday. Discuss work hours and availability with your family upfront and during the trip. Create a sample schedule that outlines work time and dedicated family time slots. This helps everyone adjust expectations and ensures quality time together.

Remember that sometimes it is hard for family members to truly grasp that remote work does not mean that you are available and free at any or all the time. My schedule meant that I was up at 6am working until 10am, then I was with the family on day trips and then home to work from 6pm onwards to close out my days. I also worked weekends to "bank" some hours for my own piece of mind.

⌚ Work Smarter, Not Harder: Making the Most of Downtime

Long train rides and flights can be a great opportunity to catch up on work. But plan ahead! Download documents beforehand and utilize offline note-taking apps and ensure that you have all information required to complete your tasks before you leave for the day. This way, you can still be productive even with spotty or non-existent internet access on the go.

We even had days where I would leave earlier than everybody else; for example we had a day trip to Florence but looking at the schedule I knew I would be in transit during a team call, so I left early by myself, got some work done on the train and was setup in a cool cafe for my team meeting while the family was in transit. It worked well.

🤳🏻 Get your eSim game on

Esims are a great way (if you have a supported device) to purchase data service especially. There's a lot of services out there but I have used the below with great success;

DENT Wireless - https://www.dentwireless.com/ 

  • You can buy and sell data on the marketplace
  • You can get "coins" for data use and daily activities
  • Was mostly reliable and no need to purchase "regional packages"
  • Data is not unlimited and can be costly if you're not careful

Holafly - https://esim.holafly.com/ 

  • You buy country or regional packages
  • Packages are for a number of days
  • Advertised as unlimited but their is a daily usage limit (different per country apparently) after which it was "throttled" and not suitable for work
  • Tethering is disabled in most countries so you can not share with family members

Global Yo - https://www.globalyo.com/ 

  • You buy quota based, country or regional packages
  • Packages are for a number of days
  • The app you use is a little weird but the internet was reliable throughout the Americas earlier this year

My approach was to have a regional plan with Holafly in Europe and Global Yo in the Americas for day-to-day use and the used DENT as a backup if I needed as it seemed more reliable. 

📍 Plan for Fun & Focus: Your Working Holiday Itinerary

Some travelers love spontaneity, while others prefer a structured plan. Working holidays often lean towards the latter, especially with family in tow. Planning an itinerary helps ensure you can integrate work seamlessly.

There are plenty of resources available to help you create a family-friendly itinerary. Consider using online apps (TripIt), templates or travel guides that suggest activities for different age groups. Remember, flexibility is key! Opt for weekend travel when possible, and schedule work around planned family activities.

I use TripIt https://www.tripit.com/ and it's amazing. It will import your bookings from your email (if you set it up to do it of course) including; flights, accommodation, car bookings, tours and many other things, and you can add your own for planning as well.

💻 Travel Tech Essentials: Gadgets for a Productive Escape

The right gadgets can make a huge difference on a working holiday. Here are a handful of my must-haves:

🎒 Secure sling bag

Forget those bulky backpacks and laptop bags that scream "tourist with valuables!" On working holidays, you need a bag that's as awesome and adaptable as you are.

Since pickpockets like easy targets, I wanted something secure but still super functional. As such I decided on a sling bag. They swing around to your front, keeping your laptop and other essentials accessible for you and safe and not accessible from others.

I searched high and low for the perfect bag, and finally found the Pacsafe Vibe 325. This little lifesaver looks great, but is tough enough to handle any adventure. My 13-inch Macbook Air fits in there snugly with all my charging essentials. Bonus: when I'm laptop-free, it transforms into a sweet daypack for exploring, holding my water bottle and storing basics.

Security geek alert! This bag is like Fort Knox on the go. It's slash-proof and has fancy lockable zippers, so you can confidently navigate even the most crowded markets with no worries at all.

Just a heads up, it's on the smaller side. While it swallows my laptop and chargers whole, there's not a lot of space for extras. 

The Pacsafe collection are all good options for more security minded people so if a sling isn’t your thing, check out their other items from handbags to backpacks at https://pacsafe.com/

🔌 Lose the Adapter Army: One Charger Conquers All!

Forget the days of overflowing bags stuffed with individual chargers and those questionable power adapters that look like they’ll start a fire any second. On international trips, I'm all about streamlining my gear.

Welcome to the glorious world of high powered multi-port chargers! No more needing a whole squad of adapters just to juice up your devices. I've been rocking a fantastic 66W GaN charger that is amazing - powerful, compact, and ready for anything. The best part? It comes with regional plugs that are interchangeable so it works like a charm no matter where I roam.

This little powerhouse keeps my laptop, phone, earbuds, and basically any other gadget I bring on a short trip happy and charged. One charger to rule them all? Yes, please!

Note: The US edition does not include an AU/NZ plug nor have I used that specific charger but it looks very similar to the one I bought from Australia

 Another option for Apple users


For longer trips I also bring along my Macbook Air charger so I have bought the Apple World Travel Adapter Kit and it has served me well throughout Europe, Asia and the Americas.

🚨 Bonus tips

📱 Airport Hacks for Smooth Sailing with Family

  • Pack all electronics (laptops, tablets) in one designated bag for easy security screening.
  • Keep your "electronics bag" clear of clutter to avoid delays.
  • Check in extra chargers and cables to minimize carry-on luggage.
  • Many airports offer priority screening and boarding for families. Don't be afraid to inquire with security and airline staff – they're there to help!

🧳 Traveling with a Stroller? Don't Get Caught Short!

  • Bring a bag that is large enough to put the stroller inside; it's a weird requirement for some airlines, especially if you want to carry it on (looking at you Malaysian Airlines)
  • Do not believe them when they say you can collect it at the planes door on departure, just have it checked through to your destination instead otherwise you will be standing around waiting only to be told that the stroller has gone straight through anyway

✅ Start planning your dream working holiday today!

With these tips and a little creativity, you can create an unforgettable experience that balances work and family fun.

What are your pro-tips for a productive working holiday?

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Chris Winfield-Blum

Software enthusiast, operations & project manager, MBA graduate, team builder, creator, developer, writer and father.

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