I used to not plan any of my trips at all. In fact, I would literally book a random, one-way flight for the next day with no hotel reservations and no further flights or anything planned… not even with the slightest idea of where I’d be going next. This worked for a good number of months until I found myself stranded in Bali last year during peak travel season with no way to leave the island on miles and very expensive hotel nights (which is rare for Bali).
I was in Doha and I figured it would be nice to fly Qatar Airways to Bali for a week or so and relax on the beach. I booked the flight a few hours before using miles in Business Class and then I booked a hotel for 3 nights in Bali and told myself I’d figure out what I’m doing next when I get there. The first two days were very relaxing, but when I started to look at flights and further destinations, I knew I wouldn’t be getting off of the island quickly for at least a week… there was nothing available on miles and revenue flights were insanely expensive for Asia travel.
I didn’t enjoy the rest of the time on the island at all as I was frantically trying to book something and find a hotel for the next few nights. I ended up switching hotels every night, which was such a hassle and I couldn’t enjoy any of it as I didn’t know when I would be actually leaving the island. Ever since that time, I book onward tickets and hotels (at refundable rates) to ensure I don’t end up in the same situation again as I did last year. However, now it has gotten over the top to the point where I try to plan out every little detail of my trip instead of “letting things happen” – so I went from one extreme to the other.
Not only that, I think I have truly been to all the places in the world that I wanted to go to which is why I haven’t been travelling as much this year as I want to… because I’ve been everywhere I always dreamed of going… and now what? To be fair, I do want to go back to a number of places I’ve been to, mainly to explore them in more detail.
I do have some trips planned for the next month or so and I hope I will be able to add on some side trips and visit new places I haven’t yet been to, but for the most part all my trips in the near future consist of re-visiting places and exploring them further.