Wow, what a great stage of life you are in. Do you plan to document your travels in any way (a travel blog, videos, a podcast)? There are many personal travel websites, but I think there's always room for a personal spin. I always enjoy reading or hearing from (former) teachers who are on the road. They often have a more thoughtful take on their situation than the average 19-year-old partying in Thailand during a gap year.

To answer your question, I do find goodbyes difficult. It's hard to say goodbye to people who have shared your daily life, to places you settled in for a while, and to different stages of life. I am very sentimental. I would be sad to stop teaching and never speak to my students again. 

Moira saying goodbye is always very hard. It reminds us that time is passing and going on. But you are going to discover places that you never visited, meeting new people that you never met.

I wonder if you wouldn’t consider writing a blog or some kind of diary. In fact your project in a way makes me dream of something I would like to do someday. So hopefully you would share your experience here on italki.

If you have bonded with someone, surely there will be a level of difficulty when you finally have to say your good bye. However, the bond you created with some of your students should not just end with italki. If it was significant enough, you could always exchange e-mails or another form of contact information. In today's world where you can send a message to any part of the world with a click of a button, we should utilize such benefit :)

Enjoy your travels!