As a single businessman, most of my travels are on business. But just because a trip is planned and paid for as a business expense doesn't mean you can't enjoy it too. To be honest, most of the big conferences and trade shows are actually planned in such a way that makes it ideal to combine business with pleasure. Some of my most enjoyable conferences have been SES in San Jose and eBay Live in Orlando. With such destinations it is almost impossible not to have fun. I remember the Sunday after eBay Live when I had some free time to spend in Orlando as one of the best vacations I had. What's great is that not only are most the expenses tax deductable, by booking online I was able to get quite a cheap flight to Orlando leaving enough spare cash for spending and pleasure.