Packing and Equipping For a Working Vacation

This week I've planned a much needed trip away from my home town of Ottawa down to Toronto, Canada's metropolitan hub. My train just departed and thankfully the in car wi-fi is working, because even though I'm traveling, I still have a busy week of work ahead.

Working telecommute, and contracting freelance as I do affords that luxury. I can get up and go for week, visit with friends and explore the city, yet still clock in hours and even remote meet with clients.

Key to making it all work is ensuring I can stay connected. To really make a working vacation work, it should seem to team members and clients as if nothing is amiss, that regular hours of operation still apply.

Doing so can be tricky, especially if you're like me and also opt to pack light, but with the right fore planning you can pack the perfect on the road kit for optimizing work and play. Here's a breakdown on the tech I brought with me for my working vacation to Toronto:

For work: 13" MacBook Air
Most importantly, I need a computer that is equal parts workhorse and ultraportable. The only option in my opinion is the 13" MacBook Air. With just enough performance and a minimal footprint, the Air barely adds weight to my day bag, but lets me have all the office I need with me at all times, with just enough screen real estate to layout most projects.

Staying connected: 2 wi-fi hotspots
The trickiest part of a working vacation is staying connected as optimally as possible. The train I'm writing this article from has wi-fi, but I actually have an important GoToMeeting just an hour after my ETA in Toronto. I can't rely on finding that one coffee shop with free wi-fi, I need to have my own dependable connection at all times.

To keep connected to the web anywhere and everywhere, I've got my Huawei wi-fi hotspot (3G). This keeps my laptop ready to connect anywhere I can find a place to sit, and despite the 3G connection, I manage fairly well to keep my workflow up. The only issue is battery life. I get about 5 hours of connected time with the hotspot and while its fine for casual use, it isn't a full work day. This is why I pack a backup, which lets me quickly swap out my SIM card for a fully 10 hours of dependable wi-fi wherever I am.

I could also go the extra mile an order an extended battery packs from China, but luckily my household already had two of these hotspots lying around making carrying the second hotspot for a bonus battery the logical choice.

For work and play: The iPad
If my MacBook Air is my business partner, my iPad is my ever faithful best friend, confidant and side kick. The iPad fills in tight spaces (like on the train) where I need to get work done but don't have the elbow room to setup my MacBook. Apps for Skype and GoToMeeting let me dial in with my team members and clients, Evernote lets me layout project notes, or scrawl my Apartment Therapy articles in advance.

Productivity aside, the iPad lets me carry all those magazines and books I've been meaning to read on a long trip, and the long blog posts I've stored in my Readability account. When laying out on the friends couch I'm crashing from, the iPad lets me hop on Netflix and watch an episode of Freaks and Geeks (my current Netflix go-to) or throw on a movie I've been meaning to watch.

At a glance: iPod touch (5th Gen)
I just picked this one up, and I love it. In many ways this is my new smartphone, despite not having a cellular connection (which I barely need, see my next point). Apple has really outdone themselves this time. The camera is great, it's thinner and lighter than anything else, and the screen is absolutely flawless. Having access to all the great apps available on the iPhone, at half the price without a contract is just way too sweet a deal.

Saying I needed to pack the iPod touch isn't really fair, since It's so small it has less of an impact then my wallet. None the less, packing the iPod was a no brainier, and paired with my wi-fi hotspot, I can use it to quickly glance at emails, to dial into Skype and GoToMeeting calls, and to quickly reference my maps (I use Google maps as a bookmark on my home screen). Right now I'm using it to listen to music on the train while I write this article (M83 - hurry up we're dreaming, a great album for a long trip by rail).

For emergencies: Samsung Galaxy S
This is the least essential part of my kit. Once my contract is up, I'll likely just grab an emergency dumb phone on pay as you go, because I just barely use my cell connection at all anymore. I have a number with Textplus on my iPad and iPod which I use for short calls or texting with friends, and my 5th gen iPod touch fills in as a portable media player and for apps.

The only reason I brought the phone was for that just I case scenario, where I have no wi-fi connection but really need to dial in with a client or if I happen to need to call 911 (literally worst case scenario). For most of the trip it will be turned off kept at the bottom of my messenger bag.

Power up: Cables and chargers
So with so many devices to keep charged up, I actually need to pre plan my strategy for staying all charged up. My laptop currently has a full charge which I won't be dipping in to until my 11:30pm meeting (as mentioned above). All my devices are pre charged at 100% and non-essential devices are either in airplane mode to save juice or just powered off.

To charge up once I reach my destination, I have all the requisite charge cables I need, a 30 pin connector, the new lightning connector (which actually lives up to its naming charging the iPod in record time) and a micro USB for my hotspots and Samsung phone.

Another handy addition to my kit is a USB hub and plug combo with surge protector. USB ports on my MacBook occupied by my iPad and iPod (I'm a fan boy I know), the extra USB port and plug lets me charge up an additional device, while keeping my laptop charged, only occupying one plug. Also I feel better knowing I have the buffer of surge protection, since you never know where you will be plugging in to grab some juice when you really need it.

Packing it all up: Luggage bag, and a messenger bag
When I'm traveling in city, I absolutely refuse to wear a back pack. I actually have three tiers of backpacks for tactical packing, (a day pack, a weekend pack, and a full on tactical mountain pack) but I reserve these for camping trips, biking and long hikes.

When I'm in the city, I generally carry a messenger bag.Right now I'm not really happy with my current option (really considering this one), which is a Toronto Film Festival canvas swag bag which while good enough, lacks some of the more adaptive features I'd look for in an urban bag. That said this bag has just enough room for my iPad, and laptop, a sketch pad (for sketching out details for projects) and a collection of various gauge pens. This bag is my day to day, and I will likely carry that kit with me everywhere I go.

Meanwhile my long-johns (a Canadian winter wear standby), warm sox, some sleepwear, extra sneakers, my DSLR kit, and a week worth of outfits are all compressed into a medium sized luggage bag. Just enough to keep me comfortable, plenty to keep me productive and connected.


I know what your thinking. That's packing light? but all in, I've got less luggage than most travel with, with enough clothes for a week of casual work and exploring the city (including extra socks and sneakers).

In general my goal whenever I work/travel is to pack without having to compromise comfort, or workflow. I manage by planning for adaptability as much as possible, for example, packing outfits that rely on layering so I can mix and match through the week. The same strategy applied to my productivity, the perfect mix of gadgets which let me pair different devices for different configurations; from all out 3 screen mobile office mode (iPod, iPad, MacBook) to a low footprint, on the train iPad Evernote session like I'm enjoying right now.

Working vacations are a great test of your ability to work remotely, and to plan and pack in a tactical way. I enjoy the challenge, and actually see it as one of the highest perks of working as a freelancer. Of course you can apply the same strategies I've discussed here to any kind of business travel. Just remember to plan smartly, and of course, it doesn't hurt to equip yourself with the right devices, for a workflow always on the go.

(image: Sean Rioux)