Planning my Itinerary, the great headache

This was the plan, 30 places in 99 days.

After posting this up on Facebook, I received a whopping 171 likes, which is way more than my profile picture (I can’t believe a map gets more likes than my face! It hurts I tell you, it really does). Along with that came a tonne of comments about safety (I’m going to Russia), recommendations for hostels and restaurants, more places to add to my itinerary and comments (mostly from my parents) about how I need to shrink this itinerary down.

Others also mentioned that I shouldn’t plan too far ahead as it might turn out to become a strict schedule rather than a chance to wonder and discover. On the other hand, it is common knowledge to book accommodation and transport well ahead of time to avoid last minute hikes in prices. What does one do???

I’m not claiming to have the perfect answer to this hellish dilemma, but I thought I’d share a few rules I’ve tried and tested that has helped me figure out what to do:

  1. Plan in chunks – Identify regions you’d like to go to and set rough dates for those places. For example, I’m going to Scandinavia for two weeks in September, after St Petersburg. That includes Helsinki, Stockholm, Oslo and Copenhagen. Do I want to venture out to nearby cities and towns? Maybe, but that comes later.
  2. Book flight tickets first – If I needed to fly from St Petersburg to Helsinki, and from Stockholm to Copenhagen, I should probably book those first because flights seem to be most sensitive to its demand. That means that the later you leave it, the more expensive it will be. According to Sonia’s travel, the ideal time to book international flights is somewhere between 1 to 3 months before departure. That’s a pretty simple and straightforward rule to follow, don’t you think? By doing this, you’ll be getting the most expensive and price sensitive task out of the way, and you can now plan your itinerary in more detail.

    Oh I wish.
  3. Book everything else after you’ve done more research – At the moment, I know that I have two weeks in Scandinavia, beginning in Helsinki and ending in Copenhagen. I will most probably be taking trains and ferries in between cities, so an Eurail pass (or the Interrail pass for EU citizens) would probably help with saving costs. It also gives me more flexibility with the dates I want to travel. If I decide to spend more time in one place instead of another, that is completely fine because I would already have locked down my travel cost between cities.**Do note that some rail services do require that you book seats in advance so a little homework will be required of you. Finally, when it comes to accommodation, let’s try not to sweat the small stuff. I’ve learned that there will always be a hostel or an Airbnb with a vacancy. For me, as long as it satisfies my two most important requirements, a hot shower and a bed, I’ll be happy and dandy.
  4. Keep track of what you’ve done and what else you need to do – I’ve been using a simple Numbers Spreadsheet to help me out, with columns for Dates of Travel, From and To Destinations, Mode of Transport and Accommodation details. If you don’t plan to travel with a laptop, perhaps print out your rough itinerary with plenty of blank spaces for you to fill up as you go along.

I hope that this has been somewhat helpful to anyone planning to do what I’m about to do, i.e. solo travel and hope to not mess anything up.