First of all, let me put in a brief plug for solo travel–is a totally underrated experience for those who are brave enough to try it. It’s probably one of the most challenging things I’ve ever done in my life because the margin for error is so small and your life is essentially all in your own hands… not to be morbid but it gets pretty intense when you’re the only one watching your back. I found that if I approached it with a “no big deal” attitude I could handle the stress and pressure of zero support system just fine. Most people wont do it because being alone with yourself while you’re out of your comfort zone (the ENTIRE time) is psychologically daunting. Plus the fear of not meeting other people or things going wrong on the road deters many people. However, its totally rewarding if you can be flexible (something I had to learn!) and realize that 99.99999% of what happens on the road is out of your control (another thing I struggled with, and finally let go of, when my ferry hit a sailboat in Greece and nearly made my miss my flight to Barcelona–no matter how many times I checked my watch or how hard I willed the boat to go faster, I couldn’t change the fact I was delayed 5 hours). Traveling solo changed me in ways that wouldn’t have happened had I had a travel partner. If you’re considering it, give it some serious thought–I don’t regret traveling alone around the Mediterranean (rather than going home early) for a second.
Now to answer your first question, I had about half of my hostels and one-way plane tickets booked ahead of time. The rest of it was completely up to me… (both a freeing and scary feeling). I bought all of my train tickets and ferry tickets the day of departure, and had an idea of what times I needed to book, but sort of played everything by ear. When I arrived at Mykonos (the first Greek island) I didn’t have a place to stay, but I met two sisters from Argentina and we bunked up together for two nights. They left a day early so I was roomless for awhile until I met a group of 4 brothers from Miami and a Canadian. We all got a 6 person tent together. Those boys met up with me on Ios and Santorini later during my trip and we had a blast together! Somehow, everything always seems to work out if you can relax into the fact that you don’t know where you’re going to stay.. for a few hours during that day (before I met the brothers) I was planning to save the 75 euro for a single room and crash on the beach with my backpack to get up for the 7am ferry. If you at least know what cities you want to visit and have a sketch of a transportation plan you should be alright. Definitely book a hostel for the two nights in the foreign city you plan to fly back to the States from. For example, my flight back to America left Florence early Saturday morning, so just in case I had problems with transportation (Euro-transport workers are infamous for going on strike all the time) I tentatively planned to be back in Florence the Thursday night before. This left me two days of wiggle room just in case I was stuck somewhere, with plenty of time to make it back for my flight. Also, don’t cut your budget too tight. Allow yourself for room for extra fees and expenses that you don’t think about when you’re planning your trip.
As for your second question, I met people on the road. I love strangers and talking to new people, and though the language barrier was a problem sometimes, I never seemed to find it hard to meet people or find people to hang out with. I never really ate alone and certainly didn’t go out alone– youth hostels are set up so you’re sharing a huge room with other girls (or girls and guy in my case) and most people are in the same boat you’re in, where they are alone or with a few friends. Everyone is out to meet people, so it has the “freshman year in college” feel, at least in the Greek islands and Spain where I was. For other European locations I would check out other blogs and read reviews on hostel websites to get a sense of the atmosphere.