I have regularly travelled alone, mainly because my friends are part of a couple, also because my job did not allow me to book in advance so was always short notice. I am in my early 40's.
I was really nervous my first time but stayed in an 'All inclusive' hotel in Kenya and had a great time.
Over the last few years I have regularly travelled to Turkey, mainly because I can book direct with the hotel/apartment which saves paying any single supplements. Usually my holiday would cost about 300GBP
I always take a book with me when I go out in the evening, usually just venture to a restaurant, so if I feel a little awkward I have something to do. I find people, mainly other women, love to chat and admire those of us who travel alone.
I am a real 'people person' but have never felt lonely on holiday. If its a choice of either travelling alone or not going at all, I know which I prefer to do!