How (maybe) to Plan a Big Trip

The Overall Take-away: Account for difficulties. Set aside some patience for the phone calls, research and paperwork.


Between my sister and I, we planned a general route, about which my sister was far more opinionated and informed than I was. How do you like being judged for not knowing the capital of Azerbaijan offhand?  I actually knew that stuff at one point (I had to in order to pass my freshman social studies class. I’m starting to know how it feels to have forgotten as much as I’ve learned) Ohh, she’s a gem… Anyhow, you may ask, why Portugal? I chose Portugal as a starting point because it is the country that boasts the Westernmost point of continental Europe. For centuries it was the end of the known world. What a concept! I want to stand there and stare out towards the land where I was born, once hidden from the Western world, guarded by the might and vastness of the Atlantic ocean. To ride to the end of the Asian continent seems a fitting goal. Like Forrest Gump, I’ll just go until I run out of land. Couldn’t be simpler. (Singapore does not boast the Easternmost point of the continent. But I can’t ride to South Korea).

There are famous pilgrim paths through Europe that I’ve heard about over the years, so I decided to hit these through Portugal and Spain, continuing into France. I figure the scenery will be good, and there is free lodging for pilgrims if you keep a pilgrim passport. Cyclists are welcome, so it was a no-brainer. I will be on the Camino de Portugese through- you guessed it- Portugal. This will take me to Finisterre, the end of the earth. There I will turn onto the Camino de Santiago across Northern Spain, and then onto the Via Podiensis into France.  This is a little backwards, by which I mean, exactly backwards from the traditional route. It is customary to head West, back toward Eden. I will be facing the rising sun, rather than following its arc to the ends of the earth, there to watch it extinguished in the sea, to begin its subterranean journey through the underworld, whence it will rise, reborn, to pour its invigorating rays down upon the quickening earth anew. I can’t wait! This path will be steeped in reverberations of those who came before.

Once I navigate my way through France, I’ll  shoot straight across a nice, flat stretch of Italy, where I can camp freely. It will be a nice gradual immersion, riding through the classic countryside of Europe and smiling at all of the friendly faces of fellow Westerners. Europe is not a great culture shock for an open-minded American.

Central Asia will be interesting. With the political turmoil in and near this area, and my unfortunate relation to a lot of this, it is impossible and/or unwise to travel through many countries and regions. I would love to visit Egypt someday, and the Middle East in general… someday. Initially, I was going to go through Iran. I was really excited about going through Iran. It is not happening.  Americans at his time cannot enter Iran without being hooked up with a tour agency, no exceptions, no loopholes. A few years ago it could be managed, but in 2017 they cracked down on travel agencies who were taking the money and looking the other way. You can get in a lot of trouble if you try, and anyone who happens to house you in this very hospitable country can be punished as well. Not worth it.

So, a two week tour costs about three thousand dollars. That is about a third of what I hope to spend on the whole trip! Also, on a tour, I couldn’t ride much. I would be carted around most of the time. I was really bummed to discover this. In fact, as it set in, I realized that I was really upset by it! I really want to visit Iran. I also want to ride all the way. I could take a ferry from Azerbaijan to Turkmenistan, but it just feels wrong. So, I decided to go up and around, through Russia and Kazakhstan. This eliminates the need to travel through Turkmenistan at all, which involves a 5 day sprint through the desert on a transit visa. I was perfectly okay with this, but why not see a little of Mother Russia, zip through Kazakhstan, for which I require no visa, and spend a little more time in Uzbekistan?


As I said, Westerners have varying difficulty getting into various countries at various times, within unfortunately regular and protracted periods of “political unrest.” Americans are plagued by the decisions of their own elected officials just like the rest of the world. It is sad to be so flatly barred from experiencing the natural and cultural beauty of parts of the world. On top of being an American, a citizen of arguably the most offensive country on the globe, there are challenges to being a cyclist as well. Visas are set up for the employed (obviously I quit my job for this trip) who are taking business trips or 2 week vacations.

Most of the countries I am visiting, however, allow me to exercise my Western privilege. I require no visas for Europe. I have to check in at the police station in Serbia within twelve hours of entry. Turkey, for me, right now, is an easy electronic visa. For the first couple months, I will be cruising carefree across the face of the Earth. Once I hit central asia, The paperwork begins afresh!

Many of these countries only allow an application for entry 3 months out. So, I will be able to apply for my Turkish visa right before my trip, maybe my Azerbaijani as well. My Chinese, Uzbeki and Tajiki visas will be picked up along the way. Pretty simple, you just look up the information on embassy websites for your country, and fulfill the requirements. So simple! Also a real pain in the ass. Frankly, I was intimidated by the tedium of this process. It was disparaging and inspiring to watch my sister find all of the visa info with ease. She is a capable sixteen -year-old, and I am an old man trapped in a young man’s body, embittered by bureaucracy and lauded as a Luddite of high order among my equally technologically feeble peers. Tis’ a wonder I’ve made it this far…

I applied for my Russian visa early because I was a little wary about all the news coverage lately. It’s an easy but spendy visa to acquire, save that the consulate makes it seem as if they are extremely busy, like a dmv (department of motor vehicles) from hell. Two hour average wait time, appointments booked two weeks out. I waltzed in there without an appointment, armed with tablet and book, ready for a four-hour experience. The place was empty. I left to visit my bank and came back an hour later, still empty. Great service! I wonder what all the hype was about.

I had to expedite my visa, which was expensive. I also forked out another 30 bucks so they could fix a small detail on my application. This was due in part to the fact that on the application, some things seem to be lost in translation. Strange questions, such as, “If you have ever had a job before your current one (I put “unemployed”) list the last two places you have worked.” You better list them. There is a place to out an address and an option to leave it blank. You better put an address. Or, my personal favorite, “Have you ever been involved in warfare, either as a soldier or a victim?” They also wanted my parents’ full names, my educational history, and to state whether or not I had experience with chemistry, explosives, firearms or any other weapons. A shout out to any vets and chemists out there. Sorry guys. Me, I’m good. I just had to provide 3 months worth of bank statements, as I am unemployed. I spent more on the visa than I will in my whole stay in Mother Russia. You are very much disproving the possibility that you are a spy.

Oh, it’s great to be American… great swaths of the world rendered inaccessible, lengthy interviews to pass through other swaths. I am a big fan of Tolstoy and his disdain for borders. It feels wrong not to be able to walk or ride across one’s own native planet without being hassled by bureaucrats. I may be hustled in other ways, but at least I understand that aspect of the world.


I have had my flight booked for months. I was sort of planning to just show up with my bike and pay whatever fee they charged me. As the date neared, I decided it wasn’t worth risking. I had to pay for my bicycle on both legs of my flight separately. It took me a few hours of calling back and forth between the domestic and international airlines It was awful. Exactly the kind of junk I cannot stand. I have removed the pedals and the handlebars from my bike, detached the wheels, and gingerly stuffed my bike and all my gear into a bike box that I got from a local bike shop. It is heavy and awkward and ready for transport!

The airline I booked my ticket through, by the way, has provided the worst customer service experience I have had, because it is almost absent: Don’t ever fly TAP (Tap Air Portugal). They get a silver medal for worst company structure. Their competition for the gold was borderline illegal, and won by a slim margin. Not that this is a particularly common destination, overall. I shaved some days off my life trying to deal with their terrible website, excruciatingly long phone service hold-times, convoluted and inconsistent website and total absence of online assistance. Award winning service. Anyhow, after another $350 my bike is guaranteed passage. I’ll admit, I’m a little bit nervous. I am still not sure how my bike will be transferred from one plane to the other. I’ll make it happen. Oh, the virtues of patience…


I opened a Charles Schwab Checking account. You have to have a brokerage account with them first, but they have no fees for membership or atm withdrawals, and you can preload foreign currencies. The consensus is that cash and card are the best way to travel. I also put beneficiaries on my accounts, and invested my spare dough so that it doesn’t sit in a bank depreciating.


On the off-chance that I get seriously injured or kick the bucket, I made a “living will” or “advanced directive.” This takes care of my “do not resuscitate” preferences, and general hospital end-of-life details. I also wrote up a sort of “Last Will and Testament” which I will have notarized. Just in case. There appears to be an element of risk in this venture! For my family’s sake, my ducks are in a row.


You know, there is a large aspect of this trip that is a setting aside of responsibility, work, and life’s various worries. All I seem to be doing is setting up investment accounts, writing wills, and becoming far more adept at planning ahead and organization. Phooey. Talk about a huge backfire!

This blog has also been quite a time sucker, mostly that Gear post, which took me ten hours to write. This post before you has been a point of procrastination as well , but look at this, I’m pretty well done!

I cannot wait to be on my bike. I have not an inkling of trepidation concerning the trip, only the accumulated stress of setting up to actually do it. I hope I have planned enough. I feel like I have done quite a bit!

There is much to learn and discover upon arrival though- where to get camping fuel, how to deal with packs of wild dogs (stick), how strict camping regulations are, and constant research about the lands before me (I want to learn about the places I visit, obviously, and maybe pass a bit of that along). It all really comes down to planning: there is a golden mean, one which affords spontaneity and accommodates  the unexpected, and also smooths out most of the bumps as far as safety and paperwork are concerned. I am one who does well within a loose structure: enough to give me purpose and direction, and the freedom to enjoy it, to play, allow it to unfold organically. Wish me luck.

Published by: bipedalgunnar

This is a blog about my trip across Europe and Asia. I am back in the States now, and turning this sequence of unedited, flurried and often poorly documented posts into a book, and hopefully a good one. That is proving to be a piece of work, but I am eager to do it. Now I'm back to work, trying to learn a thing or two about welding, get a career opportunity secured, and climb some rocks when I have a chance. Hope you enjoy it, but the book will be better *wink*.


3 thoughts on “How (maybe) to Plan a Big Trip”

  1. “It feels wrong not to be able to walk or ride across one’s own native planet without being hassled by bureaucrats.” Gunnar! Truer words.


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