Tiffany Owens writes at In Earnest about adventuring alone (something I rather enjoy, too):
Let’s begin with definitions. By solo trip, I mean a deliberate choice to enjoy a journey and destination without traveling with anyone or scheduling any meetups with friends. Of course, you might make new friends in the process, which is part of the fun. Traveling alone doesn’t have to be for the broken-hearted, melancholy, or anti-social. And it doesn’t have to always be a statement about independent womanhood either. When done well and for the right reasons, braving the mountains, a new city, or the seaside alone can be a healthy part of a holistic, well-centered life. (And you can even do it if married.)
Pulling off a solo trip is easy. Set a budget, pick a place, and write a basic list of diversions, both new and familiar. Research events and attractions ahead of time so you can buy tickets if necessary. Pack lightly, leaving enough room for shopping if you’d like. Tell friends and family where you’re headed and where you’ll stay. Once you arrive, take a walk, rent a bike, or jump on the train and explore. Tourist attractions are fun, but try also to explore neighborhoods—there’s nothing more rewarding than stumbling upon a lesser-known local haunt. Set goals for each day: reach the lake, hike a mountain, attend a workshop. Tuck in a few personal goals also like journaling, writing a new song, or taking a handful of unique film photos. Notice when the solitude “gets to you,” and instead of running from or resenting it, try to lean deeper into it.