With any trip, you must first decide where you want to go. If you’ve got a bucket list, I’d say choose based on where you want to go most first. Or if you’re restricted to a specific time of the year, I’d choose based on which destination has the best weather or best deals during that time. Or you could toss a bunch of places written down into a hat, and randomly pick one out and go with that! Most people don’t choose this option, but it doesn’t mean you can’t!