Ryan gave some excellent advice!
To that I would add check around for local gay groups who like to travel - there are many of them. Not only get to meet some wonderful people, but also get to meet people who have common interests in activities. For example, I have a great group of gays who cruise every year. Their preference is Carnival as it meets their needs and this year they're going on the Victory doing a Southern Caribbean cruise in January. Next year they're discussing doing either an Alaskan cruise or a Canada/New England cruise.
It's fun traveling by yourself, but it's more expensive. It's so much more fun traveling with family or friends as well as being cheaper. So keep looking and I'm sure you'll find someone or some group that you'll be comfortable traveling with. But as Ryan said, if you do go by yourself, you'll find cruising a great way to travel and provides an excellent opportunity to meet new friends.