Travel planning is a necessary evil (or a treat if you like that sort of thing). Personally, I detest the process – it’s onerous, time consuming, and stressful. Did I get the best flight deal? Is this accommodation going to be in a good neighbourhood? Am I going to like this place?
But sometimes, with the right tools and tips, travel planning can be easy and stress-free. I’ve worked hard over the last decade+ in sussing out the best tools and tips to make planning your next trip a breeze….and I share those tools and tips and processes with you here.
I also share with you some of my own travel planning challenges and woes along the way, in the hopes that you can either:
a) avoid my mistakes, or
b) commiserate.
Why would a 17-year digital nomad do the Hacker Paradise work and travel program? It’s not just for newbs. Learn more in this Hacker Paradise review!
Discover the best eSIM for international travel and ensure seamless connectivity wherever you go. Explore a variety of options, benefits, and FAQs to make an informed choice.
Explore Madeira’s digital nomad scene! Top attractions, hiking, events, accommodation. Learn why Madeira’s a top digital nomad destination, and plan your visit.
Digital nomads have the power to create negative – or positive – social impacts with their lifestyles. Here are social impact organizations to help us do more of the latter.
A coliving space gives you a comfortable place to live and work, alongside other likeminded digital nomads and remote workers. Check out this list of worldwide coliving spaces!
AirBnB can be overpriced and a pain. Here are 14 alternatives to book monthly accommodation, especially for digital nomads!
Here are the best eco travel companies to research and book your next sustainable travel trip!
These digital nomad retreats will help you socialize, collaborate, learn, grow, and have a ton of fun in the process.
Learn how to use WorldPackers to get free accommodation. It’s not all grunt work and dorm beds. If you choose the right gig, you’ll get way more than you give.
Here’s how Global Work & Travel makes finding travel jobs (like teaching English, working holiday visas, volunteer gigs, and much more) easy.
Digital nomad life is (lonely) work to do on your own. Here are the best coliving coworking programs to help remote workers travel, live, and work together.
Petsitting is a great way to get free accommodation and enjoy the comforts of home while you travel. But heed this cautionary – and hilarious – tale of petsitting disasters first!
In addition to being vigilant, you can get ahead of petty theft by using anti theft bags designed to deter criminals. From small to large, wearable to attachable, here’s the best in the industry.
Long-Term travel with kids might seem daunting, but it’s great if you know how to finesse it. Here are 8 tips to make it go smoothly.
By using frequent flyer miles strategically and knowing how to travel hack (ie: reading this post!), you can save even more money and even fly for free. This article is the ultimate beginner’s guide and will help you dip a toe in the ocean of frequent flyer mile opportunities.
Looking for the ultimate packing list for full-time travel? Here’s exactly what I pack to travel the world as a digital nomad – down to every last item. This interactive packing list widget is sure to give you lots of ideas for your next trip.
Want to avoid international roaming but not sure what your cell phone travel options are? There’s something for everybody, and this article outlines ALL your options along with pros and cons and what kind traveler/trip each strategy is best for.
With travel mystery shopping, you’ll subsidize travel with free hotels, discount flights, and more. Read my mystery shopping tips from personal experience.
As a foreigner, you’re an automatic target for theft, pickpocketing, and more. Scammers these days can be quite creative! Here are 24 classic travel scams (REAL scams, experienced by these pro travelers) – with tips on how to avoid them.
The internet is packed with websites for travelers, but sites come and go everyday. This is the most up to date list of the best travel websites around!
I’ve been asked repeatedly to provide long-term travel budget templates. Here’s a framework, with info on what financially sustainable travel REALLY means.
These 25 killer best travel apps will help you travel more efficiently, safely, cheaply, and fun(ly). Smartphone travel apps like these are changing travel entirely!
Some things just have to get done before you travel. Things like visas, important legal documents, even proof of onward travel! This guide outlines it all. It finishes off with instructions on how to sell everything to travel.
In this article I dissect what makes for the best wrinkle free travel clothes for women, as inspired by a capsule wardrobe challenge by Anatomie Travel Clothes. I took two tiny packing cubes of clothes and traveled ULTRAlight. Here’s what happened!
This gigantic free guide to finding free and cheap accommodation around the world is guaranteed to save you hundreds – if not thousands – of dollars on your next trip. Click through and see for yourself!
Knowing how to make money while traveling can be the difference between a lifetime of long-term travel and going home when your savings dries up. This guide goes WAY in-depth into 7 effective ways to make money while you travel.
How do long-term / full-time travelers insure themselves against medical emergencies? Expat insurance is a solution. Here’s everything you need to know.
What are the different kinds of travel insurance – and which kind do you need the most? Answer every possible question you have about travel insurance with this guide, which includes a glossary of terms and claims advice.
I’ve suffered a ridiculous number of illnesses and diseases on the road; now I’m an expert on staying healthy while traveling! Learn what’s in my travel medical kit, what supplements I use, natural cures, and all my tips and techniques for staying healthy while traveling and avoiding illness in the first place.
The best travel gifts for 2017 include the Ultimate Travel Dress, expandable packing cubes, Eagle Creek compression sacs, Chipolo tracking device, Fat Chick Goes Awol (book), and Flexiroam global data micro-SIM card. Learn more about them here!
How do you choose your travel destinations? Here’s how I’ve done it for the last 10 years, with some ideas for how you can choose your next destination.
Here are some pros and cons to solo/couple/family travel, along with resources full of testimonials from professional solo, couple, and family travelers.
I’m currently in the throes of what I’ve dubbed The “C” Trip, to Colombia, Colorado, and Costa Rica. Here’s how this trip came to pass:
In 2014 I traveled through/lived in 7 countries, and traversed over 34,000 miles. Here’s a summary of what I did, and where.
Traveling with frequent flyer miles isn’t always easy. Here’s a sordid story of dealing with US Airways, with some rules for navigating frequent flyer miles.
It’s done with the best intentions, but can have the most catastrophic outcomes. Here’s how tourists cripple local economies, and how to avoid it happening.
In just one week, $10,000 passed through my hands. And it all boils down to a stolen passport, four days before I was to travel…a saga indeed.
In 2012, my full-time travels took me to 8 countries spanning 20,000 miles. Here’s a quick recap of the highlights!
I am lucky enough to not have a university degree or a house. Here’s why I think it’s the best thing that could ever have happened to me.
A leap of faith is a scary thing. But is there a right way and wrong way to do it? Here we look at some key ingredients to making a leap of faith – responsibly.
After deciding to leave everything to chase my lifelong dream of travel, I had to walk the talk. Here are the nuts&bolts of how I Became The Professional Hobo.
Here I bare all: what prompted me to make the life-changing decision to sell everything to travel full-time. Enjoy Part I: about how it all started.
Amidst the huge effort of planning for the Ultimate Train Challenge lies a section of our trip that includes the world’s longest railway: the Trans-Siberian. Here’s how we’re planning it!
I’m leaving behind what little travel gear I own to take on the No Baggage Challenge! Find out what I’m doing and why, and check out this video of me “packing”.
The recent exercise of booking my flights back to Canada from New Zealand was a harrowing one. It took forever to actually decide on a plan of action and execute it. And for a full-time traveler, it shouldn’t have been that difficult. Then again, maybe my very freedom inspired this … Read More
I am currently recovering from Motion Sickness on the road. This is a very real, very difficult condition to deal with, and something to be aware of, especially if you’re traveling solo. In this fantastic world of full-time travel (four years and counting for me, at the time of writing), … Read More
Travel Fatigue…..it’s a bitch. This post was originally published in 2011. It has since been updated for accuracy of links and content. About a month ago, I realized something wasn’t right. I couldn’t quite define what was going on, but I had an unsettled feeling in my gut. I was … Read More
What makes you a traveler? Not always such an easy question to answer. The longer I travel, the more confused I have become about what “travel” is, and what makes you a “traveler”. And depending on who you talk to, it can be quite a touchy subject, full of egotism … Read More
What is your favourite place in the world? Boy, if I had a nickel for every time I was asked what my favourite place in the world is…. Despite being asked this question so often, I rarely have a concise reply. Instead the answer is usually a shoddily constructed response, … Read More
This post was originally published in 2010. It has since been updated for accuracy of links and content. In the last few months, I’ve had occasion to connect with a handful of people who I’ve initially met on-line, developed relationships with over varying periods of time, and then met in … Read More
This post hails to you on my first full day in Auckland, New Zealand. You may recall that I was here just a few weeks ago, which – in part – explains why I’m back, and how I planned a year of travel in the last two weeks. This post … Read More
America – the No Vacation Nation: I recently read this enlightening bit of information over at Wanderlust and Lipstick: A 2009 survey from Expedia found that 1/3 of employees don’t take all of their vacation time. While this speaks (to a certain degree) to how individuals make personal choices, there … Read More