Want an upgrade? The key is availability: All upgrades are based on it. They're also, largely, based on loyalty status. But even if you do belong to your airline's or hotel's loyalty program, you're still competing with countless other travelers for the same upgrade. To rise above the pack, it'll take smarts, a strategy, and (dare we say it) shamelessness. Here are seven brazen ways to angle for an upgrade from an airline or a hotel.
Give Your Airline Crew a Little Treat
Do: Gift something small and inexpensive to the gate agents or flight crew. Make them like you with inexpensive presents. Globe-trotting charmer Johnny Jet, a master of the art of schmoozing flight attendants, is a major proponent of this strategy. One of his not-so-secret secrets: handing out chocolates. Mr. Jet offers this advice in his Tip of the Day: "I almost always bring two boxes of chocolates—one for the gate agents and one for the flight attendants, because both can make or break your trip. When you hand the chocolates over, do it with a big smile, be genuine, and don't look for anything in return."
Don't: Assume a quid pro quo. As Johnny advises, never directly ask for anything while distributing a gift. Airline crew are prohibited from accepting gifts as bribes. Small tokens like candy or snacks are good; anything more expensive is probably a bad idea.
Speak Their Language
Do: Demonstrate your foreign-language skills when appropriate. We've seen a room upgrade go to a fellow traveler in Mexico when she flaunted her fluency in Spanish. Initiate a friendly conversation with a hotel clerk in his or her native tongue, ingratiate yourself with the staff, and you just might receive a complimentary room upgrade. Even if you're not fluent, learn a word or two. Staff will appreciate a "hello" or "thank you" in the resident language. Make an honest attempt to have a sincere conversation.
Don't: Loudly and clumsily speak a few words of the local language to staff, expecting a shower of upgrades in return. A powerful voice volume will not demystify your clumsy attempt at a foreign language.
Say It's Your Birthday
Do: Be obvious about the day you were born. You could, when checking in for your flight or hotel room, happily mention, "It's my birthday!" Wear a pointed hat and shake some maracas for the full effect. There's nothing wrong with a little self-celebration. Seriously, though, the elusive birthday upgrade has been known to happen now and again. We've heard of passengers (usually with some kind of frequent-flyer status to begin with) receiving birthday upgrades sans any effort to draw attention to the fact. Evidence of your birthday is, of course, printed on your boarding pass. And your ID. And your Keep Calm It's My Birthday shirt.
Don't: Lie. The chances your deception will be exposed are high. We'll say it again: Your birthday is printed on your ID.
Say It's Your Honeymoon (or Anniversary)
Do: Excitedly tell your booking agent that you're on your way to your honeymoon vacation. Bring proof if possible: Offer the flight attendant an extra favor from your wedding as evidence and incentive. Wear your "I'm the Bride!" T-shirt. Maybe you won't get a pair of first-class boarding passes, but at the very least, you might receive some free Champagne.
If a honeymoon upgrade at your hotel or resort is what you're after, be sure to bring a copy of your marriage license. Many resorts offer complimentary honeymoon upgrades but require proof of marriage.
Don't: Lie. Airline employees and front-desk clerks aren't stupid. I'd venture to guess that flight or hotel staff has a good gauge for who's on a honeymoon and who's only faking.
Slip the Hotel Staff Some Cash
Do: The cash bribe is a decidedly shameless activity, but there's a slick way to do it. When paying for your stay, hold twenty bucks (give or take) in your hand with your credit card and smile politely, asking whether any room upgrades or well-located rooms are available. Your front-desk clerk will get the hint. This is more effective in some places than others, of course, so it's important to proceed with caution. In Las Vegas, for example, kickbacks for cash are more likely to be tolerated, especially if you're a guest who has a good play history with the hotel. At other properties, your front-desk agent may be risking his or her job by accepting a small bribe. Be careful, be respectful, and read the situation carefully.
Don't: Bribe an airline worker. Chocolates are one thing—but airline employees who accept cash bribes can lose their jobs. Don't even try.
Bribe a Fellow Passenger
Do: Offer the guy with a better seat $100 to switch spots. This isn't illegal. There aren't any clear airline policies prohibiting flyers from paying other passengers for seat swaps. There's even an app, believe it or not, called AirrTrade that facilitates seat buying and selling among passengers. You may do this, if you want.
Don't: Have high expectations or be anything other than extraordinarily polite. Passengers are under no obligation to accept your bribe. Some folks might even be offended by it.
Show Your Loyalty
Do: Flaunt your unofficial status. Signing up for a hotel chain's loyalty program isn't exactly shameless. But advertising your unfailing loyalty to a boutique property that doesn't have a loyalty program is a bit bolder. Returning to a B&B for the third time? Write an email to the owners. Mention that you've been there a bunch of times. Tell them how much you love their property. If appropriate, write a good review. Send the link to the owners and congratulate them on a job well done. Show that you appreciate your stay, and your hosts just might show you a little appreciation in return, whether it's in the form of a room upgrade, coupons, or even just free bottles of water by your bed. Better yet, you can feel good about sharing some positive thoughts with your fellow humans.
Don't: Threaten to write a bad review if you don't receive an upgrade; anyone who does this should have their hotel privileges revoked for life.