You know where you want to travel and how to get there. Now let’s sort out when, because when might also determine if.
This is where we’re going to be victims or unwitting beneficiaries of:
That plan you just drew up on the map? It’s not done. We’re gonna iterate some more. It might take a while, but this is honestly my favorite part. It feels productive and puts my imagination into hyperdrive. First time I did this, I was glad it took so long. When I finished, it felt like I’d completed a puzzle of the night sky with ten-thousand pieces.
The process goes like this:
Start with the date you plan to depart and add a few extra months at the end.
If there were any major events you plan to buy tickets for or really just anything you simply must attend (ex. Carnevale, Holi or San Fermin), mark them in pen. You’ll gonna work around those.
Start writing in the places from your map into the calendar.
Before you write that place on your calendar, research four things:
Look up what events are happening around that time. You may want to change plans for something that will happen before or after you planned to be there.
Confirm you’ve chosen a good time to go.
Good weather doesn’t always mean clear skies and warm days. Sometimes inclement weather makes a place miserable, such as monsoon season in Vietnam. Sometimes it makes it magical. The Uyuni salt flats in Bolivia or the Lençois Maranhenses in Brazil prove moisture is the essence of wetness and wetness is the essence of beauty—but only for a few months of the year when it’s raining. Winter in Melbourne? Awful. Winter in Lapland? Hello, northern lights.
Beware weather events that shift. Japanese cherry blossoms, for example, are magnificent but they change. Ski seasons are even more temperamental. You can be off by a week or two with flowers, but a year or two off with the snow reports.
Also remember the seasons reverse below the equator and not everything in the tropics is warm year round. For proof, try spending Christmas in Hanoi or July in Cusco.
If you want to eat a haute meal, skip Paris in August when it becomes a ghost town. Almost every country has a Labor Day, and you should avoid it. And Allah help you if you end up anywhere in the Middle East during Ramadan. You’ll be having breakfast in the lobby of a Hyatt that “proudly serves Starbucks coffee.” No tagines or kofte for you.
Some monuments and nature areas close periodically for maintenance. Schedules are usually posted online. If you want to go last-minute, search social media. If someone posted a fresh selfie in the Blue Mosque yesterday, you’re probably good to see it next week.
For anything with restricted admission — say, the Accademia in Florence — secure whatever you need well in advance. The first time I want to Italy, the tickets to see David sold out so fast that i started to tell people his last name was Streisand.
This is the question and answers vary wildly. Search “Number of days” with the destination and the results will span from Americans who say ‘Just a couple days’ for the world’s largest cities to Australians who consider a week as roughly equivalent to a layover.
The truth, as usual, falls in the middle. The British and Germans tend to get it right, so I take what they say and add a day to account for ‘backpacker time” and the essential day or two off each week.
Backpacker time, since you asked, is the inevitable drift into longer and longer stays as the American road warrior instinct tapers off. It sounds like some loathsome, slacker affect, but it’s actually the opposite. Those who hustle miss the whole point of travel.
Side note: when you’re writing destinations into your calendar, consider which cities are fun on weekends. Dresden and Hué may be fine for wasting a Wednesday, but you want to be in Berlin and Saigon come Friday. And if you don’t, you’re not invited to my birthday party.
You’re nearly done! There are just two tiny hazards that can screw you. First, transit.
I know we already checked this, but we didn’t account for seasonal changes. There are things like summer/winter ferry or bus schedules and inexplicable spikes in plane fare.
Generally speaking, I don’t fight these things anymore and you shouldn't either. Just change plans and do a fun thing: go someplace you think you won’t like.
I would never have gone to Korea had traveling to Harbin been less torture and expense. Instead I want to Seoul, ate mountains of fried chicken, had some of the best sex of my life and even got a perm. You can make the most of it too.
It’s nice to know that nearly everywhere you want to go has hostels, hotels and/or home stays, so it’s easy to find a nice place you can afford. Very rarely though, you’ll plan to go somewhere and find the cost to stay has spiked wildly. If this happens, do what I do: Make it a one-night stopover flanked by two overnight trains or flights and do the New York Times 36-hours in XYZ.”
If lodging will be completely shuttered (usually seasonal), that’s probably a red flag to not go. If you truly must, then try Couchsurfing (and be weary of what happens if the host flakes last-minute). It’s really better though to admit that you’re screwed and plan to go another time.
My privacy policy is simple: I don’t share your information.
Yea, it’s just a name, email and nationality, but I’m sure there are people who would pay for it. My thoughts on that: fuck those people and fuck those fuckers who sell personal information to them. You’ll find none of that monkey business here.
If I get hacked and your info get stolen, I’ll shoot you a note to let you know. I don’t deal in passwords, credit cards or anything like that though, so there’s almost nothing for anyone to take.
To see the full privacy policy — it’s pretty boring and cost me a lot of money — you can follow the link at the bottom of the page or in the confirmation email.
Domestic American air travel is a racket run by three major companies and a few smaller ones who effectively collude on prices to screw passengers and support their bloated executives and corporate structures.
Even regional jets, which are technically independent, are fucking death traps that I literally never, ever fly.
It’s not this way in other countries, because most people are sensible and see transportation as akin to a public utility. It’s therefore common to find flights on foreign carriers for under $100. I frequently see fares less $50.
Booking far in advance is therefore unnecessary, except of course in places where tickets sell out. Avoid the temptation to book months or weeks out if you’re just trying to save money. Not only will doing so lock you into dates you might regret, you may end up paying. Why? Booking sites now sniff for your computer’s location and display higher prices for foreigners.
Rude, right? Blame the mirror. We invented that.
First, some bad news for most Americans: automatic transmissions are as rare overseas as manuals are in the US. Unless you want to seriously overpay, make friends with someone who owns an old Miata and learn.
Second, anyone who wants to rent a car should obtain an international driver’s permit. This is easy — just 30 minutes at AAA.
When it’s time to rent, don’t get tempted by lower prices with small, local companies. Go with a big multi-national.
Understand your insurance situation through-and-through. Know the limits of your credit card’s automatic coverage and have a printout of the policy. If you can get a translated copy, even better. If you’re still in doubt after all that, just pay for their coverage.
Research the scams. Before you drive off the lot, walk around the vehicle and video record it. When you return the car, do the same. Also record yourself locking it and depositing the key in the night box if you return after hours.
If you get a notice from the rental company later saying you owe for damage or not returning the car, you can send them those videos with an E-vite to go get fucked. You might also copy tourist law enforcement, so they get fined to oblivion.
It’s tricky, but you need to basically study each country’s road laws and signs like you’re getting your student driver’s permit again. Most places have tricky rules, and they love to fine gringoes like us for violating them.
In Cyprus, for example, you can be fined for eating or drinking anything behind the wheel, even a Snickers. In Denmark, you’re legally required to look under your car before you get inside to ensure no one is underneath. In Spain, drivers with poor vision have to carry a spare set of glasses. Dirty cars are illegal in Russia, as is splashing pedestrians on a rainy day in Japan.
In some places, driving is really difficult. I pity any fool who tries to drive in Cairo. You can also very swiftly kill yourself on a German highway if you’re untrained. Driving at 120 MPH is far more complex than simply pressing the accelerator further.
Fare classes are highly inconsistent.
First class in one country is generally different to first class in any other. The same is true of second, third and so on. They vary wildly by country and system.
If it’s fiscally reasonable, I choose first for early mornings and overnights. They really are better, even just for security of your belongings.
The one time I settled for a second-class overnight, I had to physically fight a mouth-breathing Russian girl who was sweating vodka and wouldn’t stop burying her face into my lap to huff my underpants like Whip-Its. I wish I was making this up, but it’s true. I arrived sleepless, angry and ugly. It ruined my first day in Lisbon and I only had five. First class would have been worth the cost. Second class is my usual go-to. For shorter trips or anything after 9 a.m. I go second.
If I want an adventure, I go even lower. Some agents won’t sell those tickets to tourists though unless you insist.
Nomads and backpackers who don’t do the travel hacking thing usually buy cheap flights. Be careful of taking that too far.
For starters, you need to observe weight limits on baggage. In the US, no one gives a shit, but elsewhere they care. The care deeply. Never buy a ticket that forces you to pay weight overages.
Seats are also important, but not for comfort. I never take bulkhead or exit-row seats unless I pay for early boarding. Both offer less (or zero) under-seat storage, so being in a later boarding group puts you at risk of having nowhere to put your carry on — or as you’ll hear them called “cabin bags.”
I’ve even been on a flight where the attendant nearly made me check my personal item. I shut that down by threatening to create a scene and de-board, but I could have avoided it by paying $8 for priority boarding.
Countless people have asked if I used an around-the-world plane ticket for my first trip.
My simple response: Don’t ask dumb fucking questions. Also, no, I didn’t.
ATW tickets are nearly useless. They typically require you to book your stops in advance, so there’s too little flexibility. The fine print is also brutal and changes constantly.
Last time I researched them, the price was based on allotments of miles. The number of stops also changed the equation. All of them required you to choose a direction (east-to-west, for example) and none permitted travel in the reverse direction even slightly. Some airlines even insisted all departures had to occur from the same point as arrival, meaning if you traveled by land elsewhere, the airline penalized your mileage allotment.
I said airline there, but ATW tickets come come from a single carrier. Instead, you buy into an alliance, of which I believe there are still only three. Quite the lack of competition there.
ATW fares do lend themselves marvelously to itineraries where you go to a different city each month and make it the base from which you explore the region. This is something we’ll talk about later when we discuss hub-and-spoke travel.
If you have status with a particular airline, you may want to consider their ATW option — emphasis on ‘may’ — but be warned that flying everywhere robs you of some great experiences.
Domestic American air travel is a racket run by three major companies and a few smaller ones who effectively collude on prices to screw passengers and support their bloated executives and corporate structures.
Even regional jets, which are technically independent, are fucking death traps that I literally never, ever fly.
It’s not this way in other countries, because most people are sensible and see transportation as akin to a public utility. It’s therefore common to find flights on foreign carriers for under $100. I frequently see fares less $50.
Booking far in advance is therefore unnecessary, except of course in places where tickets sell out. Avoid the temptation to book months or weeks out if you’re just trying to save money. Not only will doing so lock you into dates you might regret, you may end up paying. Why? Booking sites now sniff for your computer’s location and display higher prices for foreigners.
Rude, right? Blame the mirror. We invented that.
The beauty of hub cities is the slow pace. How slow you take it will vary according to the number of side trips as well as your pace. If you commit to a month though, this introduces the possibility of renting an apartment. Even if you don’t plan to stay the full 30 days, apartment rental is generally very cheap. It can also make cooking easier, which also saves cash.
Cooking for yourself doesn’t have to mean eggs for breakfast and chicken dinners. You can dial up the adventure full throttle if you sign up for a greenmarket food tour and a cooking class right after you arrive. Not only will you know what to do with the local ingredients, you’ll eat better. Plus if you know what you’re doing, the vendors may screw you less, which will offset the price of the guide.
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