We’re leaving

6 months of preparation for 6+ months of travel
While some people are able to travel without thinking too much about where they’ll go, what they’ll do, and move from one place to another along the way, we knew that this format wouldn’t work for us. Improvising isn’t something that we usually do when traveling somewhere. Why would we start now? We wanted to see and do some specific things during this travel. If we wanted to make it work without having to worry too much about the planning phase while traveling, we had to prepare our travel in advance. It would also give us more time to do some research about the best places to stay at, book excursions that require to be booked in advance (for example we booked our tickets for the Carnival of Rio in August 2017 while happening in February 2018), make reservations in great restaurants… this way, we wouldn’t have any regrets or we wouldn’t be disappointed because this specific excursion we wanted to do only happened on Tuesday, and we’re leaving on Monday! One argument against preparing so much in advance is that it removes opportunities for serendipity, that it could take away some of the fun of traveling. Now that we’re done with the trip and that (almost) everything went according to plan, I can confirm we’re both very happy we did things this way and would certainly do things the same way if we were to do it again.
Chris and I are the kind of travelers who don’t really like to stay in a hotel or on the beach for hours without seeing or doing anything. We walk (a lot), visit parks, museums, temples (so many temples in Japan), do many fun activities like kayaking, bungee jumping or anything else… so we knew that we wouldn’t have any spare time to think about organizing what would be next, while on the go.
Before starting to book anything, we had to figure out the overall feasibility of our plan — now that we had a list of countries, and approximate dates against each of them, we still had a lot of questions to answer:
“Is there any flights between those 2 places?” “Do we need to rent a car or travel by public transportation there?” “Is this train/bus do this itinerary every day?” “Can we check in late at this place since our flight will arrive in the middle of the night?” But in the end, thanks to all of this organization, we were able to travel with our mind at peace, being able to enjoy every moment of it, without having any stress about where we would sleep the night after.
The first thing we booked was our tickets to the Carnival in Rio de Janeiro. This booking made the trip become a reality. Even if we waited a couple more months before booking anything else in order to be sure that nothing would come in our way and stop us from doing this trip. Then, I started booking some accommodations. I first compared offers on multiple websites to see what was better but it was too much effort and too much time wasted in trying to save a few dollars here and there. So I sticked with Booking.com and made most of our accommodation reservations on this site, all cancellable obviously. Another benefit of using only 1 website to make all your reservations was to have a good overview of all your bookings without wondering on which site you made them. I then booked some of the flights, bus and trains. This step was way more complex than expected even if I found Google flights to be extremely useful for this part. But booking flights on local cheap airlines, in a foreign language, can be scary. I sometimes made adjustments to the itinerary based on better prices available at certain dates. We also booked ahead of time tickets to go to the Machu Picchu (which ended up being a bad idea between our booking and the day of our visit, the park decided to close at the time of our tickets for some renovation — we had to exchange our tickets once in Cusco). And we reserved some other activities like a helicopter tour in Rio de Janeiro or tour to Magdalena island to see some penguins.