Despite it being two years since I completed my trip, I still get asked how I organized my train and bus tickets for my round the world train and bus trip, so I present a short summary which will hopefully be of some help.
Russia, Ukraine and Serbia: These days, you can travel through most of Russia independently. You can purchase train and bus tickets spontaneously within Russia, or you can put in a degree of planning and pre-purchase your tickets either through the internet or with the help of a travel agent.
For a first timer, unless you can read Cyrillic, read and speak Russian or have an extraordinary level of patience and lots of time, I would not recommend buying too many train or bus tickets on the spur of the moment. Travelling through Russia needs a degree of planning which may not be necessary in some other countries.
The primary reason for the need to plan is because of your visa and the limited time this gives you. Most visitor visas are only for 30 days and I was told unequivocally that I must be out of the country within that 30 day period or I may be seeing more of Siberia than I really wanted. Timing and keeping track of the changing time zone are everything. Say, for example, your visa expires on the 14th. You may board and depart Moscow in the morning of the 14th, but not cross the Russian border until the wee hours of the 15th. This being the case, you are in breach of your visa and the peaks in the caps of the immigration people will look that much more formidable when you get taken off the train to "explain". Although I lost a day, I ensured that I left the day before my visa was to expire and I was still nervous passing over into Ukraine.
I started my trip through Russia by researching the cities and towns that I wanted to visit figuring out how long I wanted to stay in each. Armed with my draft itinerary, I headed to the tourist agency in Ulaanbaatar, Mongolia where I was living and working. I used a local agency who specialized in Russian travel simply because of the convenience and because the Russian embassy in UB issued Russian visas only through an agency, not individuals, so I was a bit snookered anyway.
There is the potential to apply independently for a Russian visitor's visa if you reside in other countries. I was able to apply for and obtain a visa through the Russian embassy in Sydney, Australia for a previous trip. But beware......from experience in both Mongolia and Australia, your visa application must be absolutely picture perfect. The embassy has no compunction to turn you away if there is even one dot out of place.
You can book your tickets online, either directly through Russian Railways (RZD) (rzd.ru) or via a cyber travel agency. The RZD site is much more user friendly these days as a lot is in English.
If you book online through an agency, make sure you know in which country the agency is located and make sure it really exists to minimise dealing with an unscrupulous group. Also, if you book online, shop around and compare the percentage taken by the agency for fees.....some of the admin fees can total over 25% of the total train fare.
As I went through an agency, I was handed an envelope of tickets. However, be warned that sometimes these are only your booking confirmation and you still need to get the actual ticket from the ticket office at the train station, or where available, the train e-ticket machine.
It is more than likely that your ticket will be in Russian. It is not hard to decipher once you know what to look for. The Real Russia site and the Lonely Planet Russia show a sample ticket and how to read it. Another source of excellent information is the Man in Seat 61 site (www.seat61.com).
If you do venture into the bus or train station to buy a ticket, first make sure you are in the correct ticket line as some lines are set aside for special people. For example, there are lines for special groups such as the elderly, members of the armed forces and heroes of the state. There is nothing more frustrating than having stood in line for 30 minutes, tolerating interlopers and, when finally achieving your goal of facing the ticket meister, all you get is a boney finger pointing you to another line.
Although I had pre-booked all my tickets along the Siberian Railroad between Ulaanbaatar and Kiev, I faced the challenge of buying a ticket at the train or bus station when I took a sidetrack to a town in northern Siberia. The handiest item I had when I booked train and bus tickets was a small pocket calendar, like the type made by Hallmark. I would write the Russian version of the month next to the English and my destination in Cyrillic and the time in the little square with the date. This was my best aid in getting the stubbornly apathetic tellers to register what I wanted and eventually issue me with a ticket. Maps are useless as no one seems to be able to read maps or are willing to make an effort to read one: all you succeed in getting is a blank, annoyed look. Likewise with arm waving or an exasperated tone of voice.
After Kiev, I free lanced it with minimal hassle but with a lot of patience while getting through Ukraine and Serbia. Armed with my pocket calendar and best russian-czech I could conjure up, I slowly learned and became more comfortable with the system. I always had a sense of achievement and a pleased smirk on my face when I finally walked out of a bus or train station, ticket in hand.
Belgrade to Prague: I again bought tickets as I went along as I was never sure where I was going to go and for how long. Most of the time I sauntered down to the bus or train station the day before I wanted to leave and bought a ticket with no hassle. The most difficult place was in Belgrade simply because the tiny ticket office was hidden in a maze of small shops. Otherwise, particularly in the smaller towns, the train or bus station was in the center of town and easy to locate. I probably always managed to get a seat because I was travelling after the peak summer season.
Canada: I bought tickets from New York to Toronto directly from the ticket office at Penn Station the day before Mum and I were scheduled to travel. I don't think you would meet with a lot of success if you did not pre-book a berth or seat on the trans-Canadian railway: travel from Toronto to Vancouver on the Canadian definitely requires a booking, particularly if you want a berth. All my tickets were booked online directly with VIA Rail Canada and all I needed to do was print out the ticket. These days you may be able to just use your smart phone.
Australia: I booked each leg of my train travel across Australia online about two weeks prior to my departures. All my bookings were made directly through Rail Australia (www.railaustralia.com.au). The only spontaneous booking was between Geelong and Adelaide when I brilliantly missed my train but did manage in the morning to book a seat on the afternoon Greyhound bus.
In November of last year, I gave myself the challenge to town hop across Australia from Sydney to Perth by train and bus, booking tickets as I went along and without taking any section of the Indian Pacific train.
I failed in my challenge. I had no problems getting from Sydney to Dubbo, taking the train through the fantastically picturesque Blue Mountains and a trip I highly recommend, and from Dubbo to Broken Hill via the bus across more typical Australian bush country. Difficulties started arising from Broken Hill. Although my map showed a railroad from Broken Hill east to Port Adelaide, the train had ceased running a couple of years earlier. Nor was there any bus. The only thing I could do was head south to Adelaide and see what transport I could conjure up from there.
With the help of the three lovely ladies at the Adelaide tourist office, we came to the disappointing conclusion that I was not going to be able to town hop across the southern, coastal region of the Nullarbor plain on Highway A1 by train or bus, where I was hoping to stop in towns such as Port Lincoln, Ceduna and Norseman. Short of hiring a car or hitch-hiking, I was not going to to get across unless I took the Indian Pacific or flew. I know the importance of the economies of scale, but it was a surprise, disappointing and sad coming to the realization that public transport across a vast expanse of Australia died somewhere in our not so distant past with little fanfare.