Calmself, I had some of the same concerns early on in planning my vacation, also my first sober air travel. I don’t know why I’m surprised, but I found that having the consideration of alcohol completely taken out of the situation actually made me more relaxed because I wasn’t worrying about where I was going to get a drink, when I could drink and all of that. I had the most miraculous vacation I’ve ever enjoyed in my whole entire life. So, the answer to how to prepare for your first sober vacation? Prepare to have the best time ever.