By Jeremy Saum

Coveting a fancier rental car, a first–class airplane seat, or a top–floor hotel room? Joel Widzer, author of The Penny Pincher’s Passport to Luxury Travel, says the key is to ask—the right way.

LIGHTEN THE MOOD Widzer favors such lines as "I see the coach section is crowded. If you’re looking to upgrade someone to first class, I’d be happy to bite the bullet."

SPEAK UP If you have a problem with your plane seat (the reading light is out), rental car (the trunk is too small), or room (loud teens next door), let it be known immediately.

TRY AND TRY AGAIN Call the hotel for a room and ask graciously for an upgrade. Then, close to arrival, ring the desk to confirm your request.

SHOW YOUR LOYALTY If you always stay at the same hotel, say so. Join airline, hotel, and rental car reward programs—and tell reservationists.

IF YOU’RE SPECIAL, BE SPECIAL When the check–in clerk asks "How are you today?" reply, "Great! It’s our 10th anniversary!"