Travel Itineraries for the Painfully Lazy and the Intensely Over-prepared



We were in Bangkok, and had finished the lunch we cooked in the hostel kitchen. Before us were several electronic rectangles, two notebooks, pencils, pens, a weather-worn copy of Lonely Planet India, and numerous cups of coffee. Two months sounded like a long time, but time seemed to slip from us as we stretched the days across the map, alchemizing hours into kilometres.

Could we somehow manage to squeeze all of our India wish-list into this paltry collection of minutes and seconds? We drew a swirling line arcing outwards from Delhi, swooping through the lower Himalayas, into the desert and out of it, sliding across the continent until we hit an ocean. It was a clean, beautiful path.

We had no real idea of how we were going to accomplish it.

South-east Asia had made us softer than blended-up puppies when it came to planning. When a path is as beaten as the one leading through Thailand and Vietnam, a backpacking sojourn just sort of occurs without you really having to do much work. You are travelling on rails, even when you seek out the stranger side-routes, the cobblestones and dirt paths. Open your hand and allow a tropical beverage adorned with a frilly paper parasol to glide into it. Close your eyes and let your feet be dragged into some majesty. Open your gob and let the noodles be shoved within the depths.

Whenever we decided, on one of our various whims, to travel to a new city, the process was simple. Someone would walk up to the receptionist of whichever hostel we were staying at and would casually mention that we planned on entering Thailand the next day. We would be asked what time we would like to go to Thailand, the level of comfort we desired for our mode of transport, how many mimosas we would like to imbibe while nestled safely away, and if we would like a complimentary backrub from wood nymphs singing forest hymns. Then we would take to the internet, find one of the eighty highly rated, appallingly cheap accommodations available for us within 24 hours, and off we went.

We became pampered dilettantes, daintily wiping our mouths with delicate doilies while trusting all of the difficult parts of travelling to well-trained, bored local people. They knew what they were doing, and they knew what we wanted. They had heard every request: every salacious, half-winked fantasy; every tedious pleasure cruise; every possible variation of what we could even fathom pursuing in their, or some nearby, nation. Insert coins, out comes vacation.


Getting a train in India is as easy as 1-2-3! By which I mean 123. There are 123 necessary steps to getting train tickets in India.

We were sorely unprepared for India, where we were actually expected to be adults and deal with our own lives and plans. Here we would ask if there was a bus or a train leading to Kolkata or Jaipur and everywhere we turned would be people struck utterly dumbfounded by our queries. The schedules, the locations, even the very existence of buses on our plane of existence were questioned and scrutinized and left unsure. Could a person travel to Mumbai? Well, that’s sort of a philosophical quandary if you think on it, and you’d better sit down and get a cup of tea, because the answer will take a while.

A sample conversation from one of our early attempts to navigate around India with some assistance. An exchange with a hotel travel advisor:

“Hello. We were wondering if you know the times for a bus to Amritsar?”

“Oh. No, not really.”

“Could we find the schedule at the bus station? Or online?”

“It’s certainly possible.”

“And where is the bus station?”

“In town somewhere, I imagine.”

“Do you know what a bus looks like?”

“I heard of one once, in a dream. It was red. No, wait, pink. Actually, it was green.”

“Do you know where Amritsar is?”

“Fairly certain. At least pretty sure. I can definitely tell you that Amritsar is not in Pakistan. Probably.”

This would be followed by some map-hunting, some needling, some careful negotiating with rickshaw drivers to not simply deposit us on the roadside and squeeze us for rupees. When we eventually came to a bus or train station we would wedge ourselves into the enormous, unruly queues, allow several dozen sneaky locals to force their way in front of us, and finally manage to walk away with tickets on a different train we didn’t really want for a price we found shockingly high.

I wasn’t always so able to trust my travel destiny to chance. As a young man headed to Europe, anxious and with lots of internet access and a delirious need for preparation, I was absurdly over-prepared for my trip. I booked every plane and train and automobile necessary months in advance, researched dozens of hostels, vied for the cheapest, yet still modestly comfortable, options and secured desirable combinations of beds and rooms. I found airport-to-city bus links, trams that would get me to desired locations.

I Google Streetviewed some preliminary walks through Paris and London and Munich, so that I knew them before I knew them. Upon arrival I strolled confidently down rues and avenues like a grizzled, old-world unfortunate, the cobblestones my siblings and cousins, every alley a friend or forgotten lover. I was on a first-name basis with every hotel secretary and hostel worker, and would email them regularly months in advance to we could build a rapport. I looked up and vetted cheese mongers and chocolatiers and creperies so that my brief time on the continent would be smooth, an unseemly reproduction of effortless travel through Europe that actually required dozens of weeks of intense research.

Every new journey I take sees a new attitude, some new view on planning, an altered temperament towards forethought. I have experienced all of the variables, have dabbled in all levels of vice-clench itinerary control. I have woken up in strange beds, unsure of where I might be sleeping the next night; I have woken up in strange beds, knowing exactly where I would be sleeping for every single night for the next two months, and also maybe what I’d eat and all of the people I’d probably interact with and their mothers’ maiden names and maybe their blood types. But new sojourns require new viewpoints, new strategies and new outlooks on how to walk. I wonder how my itinerary will look the next time I strap a bag to me, whether I will know the name and shape of my destination, and whether I will have any clue of how to get there.

8 thoughts on “Travel Itineraries for the Painfully Lazy and the Intensely Over-prepared

  1. We were kind of like that on our first trip: had to know exactly where we were, what car we’re taking, what bus, etc. Now, we’re a little more relaxed. Maybe it’s because we travel a lot and now we’re used to it.

  2. You kind of have to admit though, how truly “travelly” you feel when you are in a place like India, as you’ve described, and all the answers aren’t just handed to you on a Vietnamese platter of spring rolls.

  3. Reminds me of a friend who traveled India in the late seventies. He happened to want a train ticket so he stood in a queue. But it didn’t move and the guy behind the counter didn’t do anything but read. Everyone just waited. So he finally jumped the queue, asked the bureaucrat when tickets would be sold etc. Everyone looked quite puzzled at the foreigner. And the next question – ‘when the next train to so-and-so would be due’ – was met with equal incredulity. And they tell us it is a new Asian ‘tiger’.

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