Free ticket, short notice: Where would you go?

— -- Business travelers accumulate millions of frequent flier points and earn many free airline tickets – sometimes more than we can use. Keeping tabs on mileage accounts, program rules and expiration dates on multiple airlines can be time-consuming and often confusing. I'm usually meticulous about tracking my miles and free tickets but I recently discovered I had a free ticket award on Southwest Airlines that was set to expire within a matter of days. As far as travel dilemmas go, this was a good one: What do you do with a free airline ticket that is about to expire?

Following an intense travel period I was really looking forward to some time at home, but I couldn't stand the thought of losing a hard-earned free ticket. After all, I had endured 16 oversold flights just to get it. With the ticket set to expire in a matter of days, there was little time to plan, little time to lose and no time to find a travel companion, so this trip was going to be solo and I would have to make a snap decision.

I often fly Southwest because they operate more than 2/3rds of the flights at my home airport in Oakland. But they don't fly to many places I would ordinarily choose to go for fun. On most airlines I horde my miles until I've accumulated enough for international business class, a first class ticket to Hawaii or any long-distance flight where squeezing into economy class is sheer torture but it's too costly to purchase a seat up front.

On Southwest, award tickets must be used within one year from the time they are earned. I try to maximize my award value by using free tickets on last-minute trips where advance purchase fares have already sold out and only the highest fares remain, but there were no such trips on the horizon and nowhere else I needed to go before that ticket would expire.

With no particular place to go, I vowed to make the most of my imminently expiring airline ticket anyway. I decided to go somewhere close by, relatively inexpensive and as hassle-free as possible. I also thought it would be nice to go somewhere I'd never been and am unlikely to find myself in the future.