A Startup Founder’s Packing List for Long Term Travel

This week we’re excited to welcome veteran digital nomad and Tortuga traveler, Ben Granas. A traveler, entrepreneur, and co-founder of TripHappy, a new, data driven online travel guide and trip planner. Ben is happy to answer any and all questions about traveling or starting a business on the road, and you can get in touch with him through the links at the bottom of this piece.

Twelve months ago, I decided to leave my job and start my own travel startup. Having lived and worked in New York City for almost seven years I wanted to break out of the corporate mold and create something new. After countless hours of research, planning, and preparation, I took the leap.

Following years of living in the same city, being as mobile and flexible as possible was appealing, and that’s how the idea for TripHappy was born. Traveling on my own terms and getting off the beaten path wherever possible are important to me. Building that ethos into the company, I wanted a site that could help others to plan their own unique trips and also support my own digital nomad lifestyle. With that philosophy in mind, I said goodbye to my comfortable life in NYC to travel the world and build a business.

If you’re toying with the idea of digital nomad life, or contemplating a long term trip, this article is for you. I’m sharing what I’ve learned from a year of living and working on the road in hopes that it will help you as you start preparing for your own trip.

Choosing the Right Bag

After years of living on a tight, predetermined schedule, I wanted to be flexible as possible, and this meant traveling with only what I could fit into a single bag. Unwilling to sacrifice comfort though, I wanted a bag that could easily fit both my work and personal items.

Having tested out a ton of different bags I decided on the previous version of the Outbreaker 45. The slim design is deceiving and this bag actually fits much more than you might expect. Most bags today don’t have more than a pocket or two, besides the main compartment; so, the Tortuga’s multiple interior and side pockets we’re a big deciding factor for me. My laptop is always protected in its own pouch, and I don’t have to dig through all my stuff to find loose items, like chargers and batteries. I’m now 12 months into my trip and the bag has held up perfectly.

The accessories that round out the Outbreaker collection are what really make this packing system shine. The packing cubes will perfect the organization of your bag. The 45 L holds two full sets. The packable daypack is the perfect bag for toting your laptop around town, or loading up with the daily necessities when you’re out and about doing some cultural exploration.

Work Gear

Working while traveling means that your bag is going to look a lot different than the typical backpacker’s. For starters, you will need to carry a laptop, while others mostly travel only with a phone, but there are a few more tools you will want to bring along:

Laptop Case

Your computer is going to be moving around a lot, whether it’s in your bag, or you are just carrying it between cafes. Get a sturdy but lightweight case that can protect your laptop against minor bumps and bruises and also from rain and dust. I’m a big fan of Thule cases, but there are plenty of brands and styles to choose from.

Large USB Drive, or SD Card

Leave the giant external hard drive at home and get a 64GB or 128GB USB drive or SD card. These things are so small you barely even notice them in your computer and are incredibly valuable if your job requires you to work with large video or image files.

In-Ear Headphones

I use my headphones pretty much every day whether I am working, at the gym, or just wandering the city. You will want to invest in a good pair that can block out the noise while you’re working at cafes or co-working spaces. If you are going to be taking regular client calls you might want to get over ear headphones with a dedicated microphone so you don’t have to worry about noise in public areas.

Travel Speaker

If you work in a team like I do, it’s nice to have the music playing on a portable bluetooth speaker that everyone can listen to. These are fairly inexpensive and easily fit in the side pocket of the Outbreaker. Plus they’re instant party starters at hostels.

HDMI Cable

It may seem like a strange thing to carry, but my HDMI cable has actually saved me more times than I can count. Costing less than $10, they take up almost no room, and allow you to connect to TVs and external monitors; perfect for working or watching movies on a bigger screen.

Professional Shirt

You never know what opportunities might arise while you are traveling, so it definitely makes sense to bring at least one nicer button-down shirt. Dark jeans and sneakers will suit you fine for nicer settings (see below), but if you are trying to make a good impression with a potential client or investor, your Tiger Beer tank top isn’t going to cut it.

Personal Gear

Of course, you are also going to be living out of your bag, so you’ll need more than just work gear. Doing laundry while traveling is much easier, and less expensive, than you might think. Because I usually end up doing it once per week,  I only need 5-7 days worth of clothes which fits easily into my Tortuga. I spent most of my time in hotter weather so I brought, mostly, warm weather clothes, and also 1 light sweater for cooler days. When I ended up in places with cold weather I picked up some inexpensive long sleeve shirts and sweatpants.

My general packing list looks like this:

  • 5-7 days worth of shirts, socks, and underwear
  • 1 warm jacket: For long flights and colder weather locations
  • 1 pair of comfortable shoes: Unless you’re planning some multi-day climbs, you don’t need special shoes to travel
  • 1 pair of flip flops
  • 1 bathing suit
  • 1 pair of zip-off pants: Everyone makes fun of these, but they are actually very nice to have in places where the weather can change at any moment
  • 1 pair of dark jeans: Dark jeans are versatile enough to be worn around town or to nicer restaurants and meetings
  • 1 pair of shorts
  • 1 pair of mesh shorts: For home & sleeping
  • Durable, refillable water bottle: Stop throwing away plastic bottles and bring a lightweight, refillable bottle
  • Kindle (or other ebook reader)

Some people might disagree with me about this, but if you’re like me, you spend a lot of time reading on flights, buses, and trains. A Kindle is much easier to read on than a phone, and you can store hundreds of books to last your entire trip.

Much of the stuff you think you need can actually be picked up along the way. For example, don’t bother bringing most toiletries as you can pick these up, inexpensively, anywhere. A toothbrush and electric razor are the only things I pack; I buy soap, shampoo and toothpaste once I land. If you are going somewhere warm, don’t pack cold-weather clothes as you can always get cheap sweaters or sweatpants. And, be prepared to buy more socks – somehow I always end up losing 4 or 5 pairs when I travel.

Once you get on the road you’ll be surprised at how little stuff you really need to live comfortably. All of this gear also easily fits into a 45L backpack with room to spare.

Your Bag is Ready to Go. Are You?

Hopefully these tips have provided a little bit of insight on the packing logistics of my experience as a digital nomad. Ultimately it’s up to you to take the leap. Packing is easy; quitting your job and leaving home to start something new is the hard part. By traveling with few belongings and being as flexible as possible, you will make the logistics of the experience easier.


If you are a digital nomad or thinking of becoming one, keep these tips in mind while packing for your long term trip:

  • Pack in the Outbreaker collection for a seamlessly integrated packing experience.
  • Invest in a sturdy laptop case and always make sure your gear is protected.
  • Always be prepared for potential business meetings with a nicer shirt and a good pair of headphones for Skype calls.
  • Don’t bring more than 5-7 days of clothes since it is very easy and inexpensive to do laundry while traveling.
  • If you can buy it at the corner store, leave it at home. Pick up items like soap, shampoo, and toothpaste once you arrive at your destination.

Follow Ben, and learn more about Triphappy, on Facebook, Twitter, or Instagram.

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