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“How do you plan your nomadic lifestyle? When do you book flights and accommodations? What about Visas?”
Whenever we tell people we live nomadically, people tend to assume we move around all the time, that we are CONSTANTLY on the go. How could we possibly have time to see everything, work on passion projects, and still enjoy ourselves? Wouldn’t all our time be spent on travel planning?
I get it. Some people find travelling pretty hectic, and if you read this post from the MadFIentist, he actually mentions that he tried the travelling lifestyle after quitting his job recently, and it wasn’t for him.
With all the flights, accommodations, activities, Visa requirements, navigating the local scene—from food to language to customs, it can all seem overwhelming, but fear not, my young grasshoppers, here are some tips and tricks we use to keep ourselves sane and happy while traveling.
Slow it down. Waaaay down.
Back when we were working, every vacation was a sprint. I would make detailed hour-by-hour vacation schedules (yes, I was one of THOSE psychopaths) dictating all the places we had to hit in order to get the maximum value out of our short, overpriced vacations. I had to make every second and every dollar (and there were LOTS of them) count. On our trip to London, this backfired when some of our excursions got cancelled due to bad weather, and I nearly had a nervous breakdown reshuffling the schedule, trying to refill the slots, while not missing any crucial attractions. Wanderer was NOT impressed.
Now, instead of staying only a day or two in a place, and moving around all the time, we typically stay for a few weeks up to a month.
I have to say, I enjoy SLOW travel way more than FAST travel. It’s much better to stop and smell the Boquete coffee, savour the Mexican ceviche, and really get to know what it’s like to live in a place rather than moving around every few days. We generally look up the top 10 things to do in a place, and try to see only one or 2 things per day. If we don’t end up seeing them all before moving to the next place, that’s perfectly fine. In the evenings, we mostly chill out at our AirBnb and do some coding, write a blog post, or answer comments/e-mails. This makes travel SO much more enjoyable because you’re not trying to cram in as many activities as possible, and you give yourself time to organize and figure out how to get to the next place.
Book Flights At least 6 Weeks Out
Since flights are the most expense part of the trip, we like to book flights at least 6 weeks in advance. For long haul flights, we try to travel hack and use frequent flyer miles as often as possible. For short haul flights and flights where we can’t use miles, we use have a whole smorgasboard of tricks and tips to save money on flights, but since this is a whole topic in of itself, we’ll be writing in detail about this in a separate, upcoming post.
Book Accommodations A Month In Advance
I tend to book Airbnbs at least a month in advance and I look for ones that have a “100% Refund” clause or a “Flexible” Cancellation policy. With the 100% refund clause, you get all of your money back, including the Airbnb fee (which is generally around 6-12%). The “Flexible” Cancellation option gives you your money back minus the Airbnb fee.
The reason why I like choosing this option is because it lets me book as early as possible (to get the best picks, as volume usually goes down when you get closer to the date in popular cities), but if anything unexpected comes up (like if we end up changing our itinerary to meet up with friends or if a local recommended a better place to visit), we can easily cancel and rebook a place in a different city without losing any money.
One of my favourite things about Airbnb (other than the fact that they helped us save over $18K/year by providing us with the ability to cook and do laundry) is their impeccable customer service.
There were several incidences where a host listed an amenity (like hot tub) and then charged extra for it. Airbnb simply reimbursed me the charges without question. Another time, a host had to cancel a REALLY good deal in Amsterdam ($53/night for an entire apartment!) due to a health issue, and Airbnb let me re-book a new place for $90/night and re-imbursed me the difference. All because the host cancelled 3 weeks before my arrival date and there were no more comparable deals by then.
Generally, I like to book accommodations at least a month in advance using the “100% Refund” option and then make changes if our itinerary changes.
There have been incidences where I’ve booked an Airbnb two weeks in advance, but I find that you get a limited selection if you do that, and the prices are not optimal.
Readers have asked whether we’ve ever just showed up at a place without accommodations and looked for one on the spot. And the answer is NO NO A THOUSAND TIMES NO! That’s how you get screwed with shitty places and high prices…unless you’re a backpacker and are okay with just sleeping in a dorm (we’re closer to flash-packers, so this wouldn’t work for us). To get the best value for your money, it’s better to book at least one month in advance and in the worst case, 2 weeks in advance. Keep in mind that this is a general rule of thumb, but in really popular places like Edinburgh, Copenhagen, Amsterdam, or Zurich, you may need to book even earlier than a month in advance. But for more off the beaten path places like Oaxaca, Merida, or Nha Trang, you’re probably okay to book less than a month in advance.
Also, keep in mind that there are weekly and monthly discounts on Airbnb where you can save up to 60%! This varies depending on the host, but we’ve found cases where a 7-day stay can be LESS expensive than a 6 day stay. So keep your eyes peeled for these deals.
Divide and Conquer
If you have a bunch of countries in mind, you might get a bit overwhelmed in terms of trip planning, figuring out where to go, which flight to book, where to stay, etc.
This is when I like to use my favourite saying “The way to eat an elephant is one bite at a time.” (If you’re a preachy “holier-than-thou” vegetarian/vegan who’s offended by this phrase, please know that for every comment you make complaining about this fact, I will eat one elephant in your honour. “sharpens knives* *puts on elephant-eating bib”)
First, figure out the flights. This is the most restrictive and costly part of the trip. Use travel hacking to fly for free as often as possible. For flights that you can’t use miles for, book as early as possible to figure out the more cost-effective route.
If you’re going to Europe, you’ll want to consider other options to get around, once you’ve arrived via a major hub (generally the cheapest, most optimal flight to get there). For example, Megabus, and National Express in the UK and FlixBus in Europe can take you as far as 500-600km for as little as 5 Euros. And look for budget airlines like Ryanair, and Easyjet to find cheap flights to get to destinations that can’t be reached by bus.
We like to use google.com/flights to find the most optimal flights (the calendar option is especially good for figuring out price dips during the month) and GoEuro.com to find cheap bus or train travel routes throughout Europe.
Next, work backwards to figure out how many days to stay in each place and book your accommodations.
We like to use Airbnb in Europe, Central America, and South America because having a kitchen and laundry saves you big bucks for travel (if you’d like a to get a $40 USD off for your first Airbnb booking, click here)
In Asia, we like to use agoda.com or booking.com (click here to get $20 USD off your first stay) to find hotels. Since eating out is ridiculously cheap in Asia, not having a kitchen isn’t a big deal.
Once you’ve figured out the main pieces (flights and accommodations), then you can figure out the nitty-gritty details once you’re on the ground, like attractions and food.
Once you use the divide and conquer method, travelling will get a LOT easier.
Give Yourself Time to Acclimatize
When you first arrive in a place you’ve never been before, your first meal will likely suck, be overpriced, and not at all be something the locals would flock to. As much as I pride myself on maximizing the ever-loving crap out of everything, I know to cut myself some slack on my first day. This is because when you first arrive at a place, you’re tired, you’re jetlagged, you may not speak the language, and you haven’t figured out where the locals go yet. So you haphazardly grab a meal close to your Airbnb, just to satiate your ravenous stomach which is now growling so loud people are starting to stare.
This is okay. Accept it. We know that our first meal or grocery trip will be crappy because haven’t yet figured out what a Chedraui (Mexico), Hawker Stall (Singapore), or Bukit Bintang (Malaysia) is yet.
Which is why our spending is generally high on the first day, but quickly levels off after that. Because by the 2nd or third day, we’ve quickly figured out where the local “Mercado Principal” is, marked down the best 40 peso buffet place, or found the food heaven that is the Singapore Old Airport Food Hawker Stall.
Wherever you are, realize that your first meal/grocery trip is likely going to suck, cut yourself some slack and know that the longer you stay, the better you will be at finding the best local deals. Trust me. This happens to us. Every. Single. Time. It’s just part of the process.
Check Visa Requirements
One of my favourite things about being Canadian is our passport. Because the Canadian passport is a golden passport, we’ve gotten Visa-free entries to every country we’ve travelled to, with the exception of Cambodia and Vietnam.
For Cambodia, we had to apply for an e-visa beforehand. It cost like $35 USD each, we had to print out a document to show to the immigration people, at which point they stamped us in.
Vietnam was weird. We didn’t need to get a visa from an embassy, but we needed to pre-apply for a visa at an online travel agency which issued us an authorization letter from the government. We then presented that printed out letter to the immigration desk at Ho Chi Minh and got issued a visa on the spot. This is called a VOA, or visa-on-arrival.
Americans, Europeans, Australians, and Canadians automatically get a 30-day Visa-free entry to Thailand if you fly in and a 15-day visa if you enter via train. After staying for a month, we wanted to extend our time, so we simply went to the Visa office in Chiang Mai (about a 30 min drive outside the city) and paid to get our Visa extended.
Before travelling, check what the Visa requirements for the country you are going to given your passport. Generally Europeans, Canadians, Australians, and Americans have golden passports that make it easy to enter many countries without Visas but check with your State Department on the most up-to-date requirement.
Cover Your Ass with Travel Insurance
Before you travel, MAKE SURE YOU GET TRAVEL INSURANCE! You can go without insurance for things that won’t bankrupt you, like trip cancellation or trip interruption, but for medical (especially if you’re going to the States), you NEED to get insurance. Otherwise you could be out hundreds of thousands, even MILLIONS of dollars if you get seriously hurt and need to stay in the hospital for an extended period of time.
We buy worldwide insurance from WorldNomads that includes trip cancellation and interruption, which saved us thousands of dollars when Wanderer’s grandmother passed away suddenly last year and he had to fly back. Click here to read my post about travel insurance and to get a quote (full disclosure: this is an affiliate link, so we will get a small commission if you purchase travel insurance).
So there you have it. Travelling doesn’t have to be stressful if you put a system in place. For us, during the past 2 years that we’ve been travelling, we’ve never missed a flight, never run into a major problem with accommodations, and the only thing that’s gone wrong is having to fly back home because of a family emergency. But because we were covered by travel insurance, we didn’t have to worry.
Phew! How do you summarize 2 years of travelling into one article? The short answer is you can’t, so this article feels a bit like scraping the surface of multiple topics that could easily fill multiple articles. So if you want more details about any particular thing, let us know in the comments and we will tailor our next few articles to what you guys/gals want to know!