Scoring a hotel room upgrade is all about timing. It's going to be easier during slower times, surely, but it also makes a difference when you ask for the upgrade. A few seconds at check-in can make all the difference. If you wait for the front-desk person to hand you a key, you're likely to get the least fancy accommodations.

But if you make nice, telling them it's a special occasion or that you have a lot of work to do, and you do this before they've locked you into a particular room, it's much easier for the agent to hook you up.

Even if that moment has passed, all is not lost. Two years ago, when my husband and I went to St. Thomas for his birthday, our original room was a dark cave directly above a noisy outdoor bar. A quick trip back downstairs, a little explaining that it was a special occasion (while kicking myself that I hadn't mentioned this when I checked in), and we were reassigned a room with an ocean view and a private balcony.