While surprise hotel upgrades have fallen into my lap time to time, they happen most when I've taken some sort of simple, strategic step. It hasn't always been intentional but it almost always yields results.
See, hotels are in the business of wanting to make guests feel welcome and special. In a place like Las Vegas, or those available suites near anaheim convention center, for example? Those massive hotels are sitting on loads of upgrades and perks to be handed out. So it's all about saying the right things to make sure you're in line to receive those benefits.
These are some tried-and-true ways to finagle a free hotel upgrade or another perk. I have my eyes on the breakfast buffet.
I follow the "you don't know until you ask" philosophy; asking never hurts. Whether it's for Wi-Fi or a free room upgrade, I've learned that nicely and politely inquiring about any benefits that might be available is sometimes all it takes. (Also, it helps to be discreet and not inquire in front of other guests, because it's likely not everyone can get hooked up.)
The worst I can be told is no and then I'm in the same position as when I started. The best I can be told is yes and then I'm better off. Low risk, high benefit.
Even when I think I know the answer, I'll still ask. At one hotel I stayed at, for example, I called to ask about Wi-Fi. It was pretty obvious since I couldn't log in that the hotel charged for it but I dialed to investigate the situation anyway. Here's how it went:
"Hello, I was wondering how I can access the hotel Wi-Fi."
"Well, we actually charge for Wi-Fi but I'll can waive the fee for you for the days you'll be staying with us."
That was it. I had no special status or anything. All I did was ask. Perhaps the person I spoke with was in a good mood or was embarrassed herself that her business-friendly hotel charged so much for something that (I believe) should be free. Everyone was happy.
Slip the person a "tip."
It's the oldest trick in the book and when employed tactfully, makes everyone happy. The easiest way to oil that upgrade is to accompany it with some cash, though it requires some art. I usually don't pick this method because I'm afraid I'll bungle it and make everyone feel uncomfortable. That said, I have seen it employed tactfully, though, and to great success. If only I was that smooth.
It doesn't have to take a Benjamin either. I've seen a nice token of appreciation in the form of a $20 bill will do. I always remind myself this is the hospitality industry where tips are welcomed and often relied upon, too, so there's really nothing greasy about it.
Mention special occasions.
Honeymoon, anniversary, birthday, half-birthday, whatever it is, that celebration information should always be relayed to the hotel staff deftly. The best way to do it is to mention it when the reservation is made and then when you check in. Hotels are honored to be chosen for momentous day, and it gives them an opportunity to really show off — to the guest's benefit.
From little touches (cakes delivered in the evening) to the big flourishes (suite upgrades), you can bet some manager has filed these away to pull from at the first hint of a special occasion.
Mentioning a birthday when it really isn't is like the big-fish version of telling the restaurant server it's your special day for a free piece of cake (if you don't mind the whole establishment singing to you). I'm too embarrassed to ever do that but people definitely do play pretend.
Join a loyalty program.
Even if I'm staying with a chain I don't think I'll be checking in with again for a while, I'm still inclined to join the loyalty program. Why not? It doesn't hurt to accumulate points and a hotel loyalty program is an easy way to distinguish oneself from all the other guests and get into the pool of guests worthy of privilege, perks and upgrades. You'll still be given priority over guests that aren't part of the loyalty program, and this includes overbooked rooms.
Skip the e-check in.
Checking in person adds a nice touch to the whole hospitality element. And it's the human touches that make the most difference. See a pattern here?