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Ask Peter: How to Score an Upgrade & Senior Travel in Hawaii

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Fast, cheap and easy. As the old saying goes you can have two out of three, but not all three. Instead of just looking for the quick fix, ask Peter and he’ll help you travel smarter!

You can talk to him at 1-888-88-PETER (1-888-887-3837), email him at,  tweet questions to @petersgreenberg (use #askPeter), or post questions on his Facebook page. He will be standing by to take your calls today at 6pm.

This week, Peter shows you when you can and can’t expect to score an upgrade, the right time to book a cruise and how to plan your in-laws’ Hawaii getaway.

Larry in Los Angeles asked: Would you please suggest a way to approach a ticket agent when checking in at the airport and asking for an upgrade?

The best way to ask for an upgrade is not to ask for one at all. The best way to get an upgrade is not even to mention it. Remember, it’s more important to be interested than interesting. It’s more important to really have a conversation than to schmooze.

Nobody ever talks to these ticket agents. They get abused by their own airline before they get abused by you. I challenge anybody to tell me the first and last name of anybody who works at an airport. Even if you are a frequent flier, I’ll bet you that you can’t.

Don’t expect an upgrade when you established no relationships. If never even had a conversation other than, “Can I have an upgrade?” Then the answer will be a big, “No!”

It doesn’t work that way. The best way to get an upgrade is to engage that ticket agent by having a conversation. Ask about his or her job, what kind of day they had, what the weather’s like, how the Yankees are doing — anything other than that upgrade. Then you write a thank-you letter. By the third time you come back to the airport, it’s an alumni reunion. They’re happy to see you, because you took the time to talk to them. Before you have the chance to do anything or ask for anything, they say the five magic words: Let me see your ticket. You know what that means. You’ve just been upgraded without ever having to ask for it.

For more information, check out The Travel Detective Talks Upgrades.