Look Over My Shoulder Stage 3

Learn how I plan a train journey from London to Tbilisi

Look Over My Shoulder

Stage 3: Building a Skeleton Itinerary

This is Part 3 of a series of articles walking you through my travel planning process—from barely an idea to reservations and actual travel. I recommend reading the articles in order:
Stage 1: Introduction & the Dreaming/Brainstorming Stage
Stage 2: Solidifying My Goals

In this post, I will talk about how I begin building my draft itinerary.

Map showing preliminary itinerary for trip from London to Tbilisi

As usual, I have found myself starting with one specific place to visit (Georgia), and before I know it, I have added more and more destinations. This happened in a big way in my 2017–19 odyssey—I started with a plan to walk the Camino de Santiago and then go back to the USA. Then I kept adding countries until I my trip lasted almost two years.

Here we go again.

Summary of the Plan Based on my Goals

So, my main goal is to get to Georgia. Add to that:

  1. Reduce my air travel as much as possible.
  2. Travel overland (mostly by train).
  3. Embark as soon as possible. This probably means a winter trip (low season).
  4. Stop along the way for a few days or longer to connect with people and see special places.
  5. Travel with a limited budget.

And we have: 

A train journey from London to Georgia in the winter of 2022, stopping along the way to see interesting places and to meet locals. Try to keep my costs low without too much discomfort.

(You can read the details of how I came up with these goals in the previous post in this series here. )

Research, Research, Research

Here are the on-line tools I use to do travel planning:

Now is the time when I create a Word document where I record data as I gather it: train routes and fares, lodging possibilities, places to see, etc. Each country has its own heading with categorical subheadings. The document starts out looking something like this:

Sample planning document

Later, in Stage 6 this document will become an indispensable tool for detailed planning.

Alternatively, there are many kinds of note-taking apps available that help you automatically categorize and sub-categorize topics. I have successfully used One-Note in the past.

My Own Version of the Orient Express

The Orient Express no longer exists. There is a very high-end luxury touristic version of the train that you can read about here. It is not a train for people like me who have to travel on a strict budget. But I can certainly recreate the journey with a little help from The Man in Seat 61.

Mark Smith, also known as “The Man in Seat 61,” provides more information about train travel than you will ever need. Because of the great service Mark provides for free, I always try to purchase train tickets through the links on his site, enabling him to earn a small commission.

Slowly, using all my resources, I developed my skeleton itinerary.  Using cut-and-paste and lots of quickly jotted notes and ideas, my planning document expands day by day. I record the expected costs of tickets, lodging, etc. as I encounter the information. (More about that in my next post.)

My Skeleton Itinerary
Fly to London
  • Side trip possibility: round trip to Bristol to spend some time with my friend, Annie
London to Paris on the high-speed Eurostar train
  • Only one full day (two nights)  in Paris to walk around a bit and maybe take a free walking tour.  Paris is really to expensive for my tight budget to spend much time there.
Paris to Venice (a full day of travel)
  • I may stop in Annecy, France for a day or two to enjoy a beautiful small French village.
  • Two to three full days in Venice, a small city with a rich and interesting history.
  • Venice had pretty much been removed from my bucket list because of the problems over-tourism has caused. But I learned that there are few visitors in mid-winter and accommodations are a bit cheaper.
Venice to Zagreb, Croatia
  • Now that I will be in the Balkans, my travel can slow down a bit for two main reasons:
    • It is much less expensive to travel/eat/sleep in these countries
    • The culture will be more different from mine than the Western European countries, making it more interesting to interact with locals. These are former Soviet Bloc countries which gives them an interesting modern history and culture of their own—one which most of us from the United States never learned about in school.
Zagreb to Split
  • Possibly visit Split for a few days
Split to Poderica, Montenegro
  • I need to travel by bus because there is no train available for this segment.
  • Montenegro is the perfect example of how I keep adding countries to my itinerary. I originally did not include Montenegro on this trip intentionally. Then I learned that my friend Annie might meet me at various places along the way. Annie would really like to go to Montenegro. So BAM…I added Montenegro to the list. That is how easy a one-month trip turns into a half-year.
  • A couple years ago, I made a plan to visit Montenegro in the winter, so I have lots of research already completed. For example: https://sofiaadventures.com/montenegro-in-winter/
Poderica to Uzice and/or Belgrade, Serbia
  • One of the most beautiful railroads in Europe makes its way from Poderica through the Balkan Mountains. I expect during the winter, this may be stunning.
  • Serbia is a very inexpensive country with welcoming people and lots of interesting places to visit.
  • As I began research for Serbia, I decided that it might be a good idea to spend some extra time here—possibly up to a month.
Belgrade to Sofia, Bulgaria
  • Sofia is another promising place to plan a longer stay—maybe a week.
  • From Sofia, I will make a long side trip to Greece just in order to see Meteora. Then I have to return to Sofia to travel to Istanbul.
Sofia to Thessaloniki and Meteora, Greece
  • It is a two-day trip to Meteora that includes an overnight stop in Thessaloniki each way.
  • The monasteries of built into the hillsides of Meteora have fascinated me for years.
  • This is another place that is crammed with tourists during high season, but from accounts I have read, it is mostly empty in winter, making it easier to hike from monastery to monastery.
Meteora to Sofia
  • I am pretty sure I have to return all the way to Sofia in order to catch a train to Istanbul.
  • This is an opportunity to add a few more days in Sofia if I have found it compelling.
Sofia to Istanbul
  • Overnight train in sleeper cars. It has been 50 years since I slept in real sleepers on an overnight train. I am actually looking forward to it—even though we will be required to disembark at the Turkish border at 1:00 am to go through immigration.
  • I must stay a few days in Istanbul, at least!
Istanbul to the Border of Georgia
  • This will take at least a week as I make side trips to Pamukkale and Goreme (Cappadocia) along the way.
  • Turkey is a vast country and deciding on a few places to visit is challenging. However, in these early stages of planning, I should anticipate that by the time I am in Turkey, I may be getting tired of moving around so often and ready to make my way to a somewhat more permanent “home” in Georgia—my original goal.


Up Next: Testing My Budget

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