But I was in Italy for 2 weeks alone last year. Oh and it was also my first trip EVER! I will never forget how I felt to get on that plane alone. And if you wanna go alone, Italy is a great place to go as it’s so tourist friendly. I admit that when I was there I got lonely but when I came home I realized that I like the freedom. I’ve now got a 4 week trip to Greece planned for this June.