We are taking a trip around the Pacific, South East Asia, and India. Starting in the UK, we make stopovers in Portugal and Dubai to visit family, before starting the trip “proper” in Singapore. From there we head SE to Brisbane and roughly follow the map below.
Travellers Point is a fantastic tool for sketching out the trip you are planning. I found it let me break down the planning into manageable chunks, weirdly those chunks have stuck in my mind so I now think of the whole trip as six distinct sections. When I try and take a step back to look at it as a whole, it can still feel a bit overwhelming.
Like most things in life, breaking down things into manageable chunks helps you gain perspective on the problem in hand. I wanted to avoid flying across the Pacific over the Christmas holiday period, so I gave the Australia and New Zealand chunk a hard stop in very early December. This in turn made it a lot easier to plan for Christmas and New year in South America, getting there with plenty of time to sound the place out ahead of the holiday period in order to get the most out of it. It also helps with planning for the local weather conditions, although some countries are a law unto themselves when it comes to that.
I would advise against planning your trip in micro-detail on one map. Try mapping your chunks in detail on their own distinct maps. If you do this then new ways of linking your chunks together will become clear.
For example. We were originally planning on starting the trip in India and working our way through SE Asia up to Japan. From there we planned to fly down to Australia, and head onto the Americas, finishing the trip there. As much as I tried, I couldn’t make the itinerary work with regards to seasons. By making the starting chunk Australia we were able to make sure that our southern hemisphere stops fitted into spring, summer and fall and when we get to the USA it will be spring again. No winter for two years…winner!