I think it's sensible to stay close to home for your first trip. Maybe look for somewhere that's easy to get to and come home from, but possibly a different environment than you're used to. Cities might be easier to access and often have lots to do to keep you entertained. I don't know if you live within easy access to seaside or countryside, so completely refreshing but can feel isolating and may not be as easy to get back from.
I think if I were you, I'd firstly make sure I was visiting somewhere where it's relatively easy to get back home if you're feeling unhappy.
Then perhaps set a budget for how much you might want to spend. You can book most places online so that makes things simpler and less anxiety-provoking. Maybe it's worth starting in a hotel where there might be a coffee shop you can sit in and the front desk is run 24/7, they're more predictable. But B&Bs are lovely too.
I don't think it sounds wrong that this makes you nervous at all, but I think it's an excellent idea.
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