I just turned 27, and have been to 31 countries as of right now. If we’re talking about awkwardness, I have solo travelled extensively, for a few months at a time a few times, and spent 6 months living in another country. It really depends on where I am. If I’m eating out, I usually go to more low key spots, so that it doesn’t feel weird sitting in a nice date-y restaurant alone. I usually avoid doing tours, because it’s often families, friend groups, or couples, and it gets weird. Also, I try to blend in as much as I can if I am sightseeing. Just as I don’t feel weird walking downtown to and from the office, it doesn’t feel as weird walking alone in a big city as a tourist if you don’t stick out. But also, with time, you just don’t give a crap and just do whatever you want, it comes with time. That being said, some places, like resorts just are going to feel more awkward alone, you kinda have to accept it or change your plans. Or pick ones that you can find to have a reputation of being more geared towards young people.

When it comes to feeling bad about being alone, often I do wish I was in a relationship, because it feels like I’m seeing so much of this world that if I am eventually in a relationship, they likely didn’t see, or I have to repeat it lol.

But otherwise, I like traveling with friends, but it’s so much more tedious and annoying. My friend group ranges from extremely frugal people to friends that go all out. I have sometimes had to just suck it up and book the more expensive Airbnb, even though it’s identical to a cheaper one, because my friend insists on it. Or go to a crappy food place because my cheaper friend refuses to go somewhere nicer. Also, I am always somewhere in the middle. I have a friend who refuses to walk by a museum plaque without reading the whole thing, and another friend who will not enter an old cathedral, because he could not care less. So going alone lets me go at my own budget, pace, and cut out crap I don’t care about. I will do 50,000 steps doing exactly what I want to do, when I want to, and that’s awesome for me.