Last Updated on June 22, 2020 by Amanda Stancati

Want a luxurious hotel suite without the price tag? A convertible to tour around in? A seat in first class? Souvenirs for a fraction of the cost? For this week’s Editor’s Pick, long-time traveler and blogger, Nora Dunn shares with tripcentral.ca tricks and advice in getting free discounts and upgrades while traveling.

Free Car Rental Upgrades

I drove around Hawaii in a blue convertible, for the price of their base-level compact car. How? The clerk asked if I wanted to pay an extra $20/day for an upgraded car. I said “No thank you – but do you have any free upgrades available?”

Without batting an eyelash, the clerk disappeared into the back, returning with the keys to my shiny convertible – gratis.

Car rental agencies usually have a designated number of “free” upgrades available, for customer service issues or gestures. If they don’t need the upgrades for other customers, they’ll give them to you; all you have to do is ask.

Flight Upgrades

A few years ago, I charmed my way into first class on a domestic four hour flight by casually chatting with the gate attendant as she was getting ready. Again – I simply asked her if there was any room up front. She took my boarding pass, and with a smile and wink, returned a first class boarding pass to me.

This happened one other time while awaiting my fourth flight on a hellish 50+ hour trip; I described my itinerary thus far and begged the gate attendant for a better seat so I could sleep. It was only a two hour flight, by my weary self appreciated the extra room.

Free flight upgrades are increasingly harder to get, but it’s still possible.

Frequent flyer miles are another way to get free flights and upgrades. You can collect miles without spending money (per se) or flying, and it’s worth some leg-work to fly long-haul in business class.

Free Hotel Upgrades/Discounts

There are a few ways to negotiate hotel discounts and upgrades:

1) Phone in advance to reserve and ask for a discount. (If you charm the right receptionist, you’d be surprised at the results). The longer you stay, the better your chances of a discount.

2) Walk-in late at night. During off-peak seasons if you arrive in the evening and they have space, ask for a discount or upgraded room based on a late check-in. Their chance of another walk-in is slim; ask for the manager if the desk clerk can’t help, and be prepared to walk out to the next hotel if they don’t comply (they might call you back in).

3) A risky upgrade strategy is the “passport trick” – put a cash “tip” in the photo page of your passport when you hand it over to the hotel clerk to register you. As you do, ask if they have any nicer rooms available. I’ve never bribed anybody, but I recently read that this trick is apparently successful.

Discounted Shopping

Whether at home or abroad, you can get discounts while shopping – even in unlikely places. In some cultures, haggling is actually expected. Even in “regular” stores around the world, managers often have authority to give a discount when necessary – usually 10-20%. Here are a few ways to ask for it:

1) Find damaged goods. If you like that shirt, find one with a missing button or loose thread. Point out the flaw, and ask for a discount. Once you get it home, a quick repair will make your item new.

2) Ask for a bulk discount. Buying items in bulk while traveling is impractical, but if you’ve found a small souvenir that will suit a few people, or if you’re buying multiple items from the same store, you’re entitled to ask what they can do for you.

3) On the premise above, get together with other travelers who want the same thing and negotiate a deal with the merchant. It’s best if one person goes in to negotiate and pay; you’ll get a better response.

Pulling it Together With Body Language

There’s a little more to asking for an upgrade than simply asking. It’s how you ask. If your body language says “no” while your words say “yes”, body language wins.

Carry yourself with confidence, and expect the upgrade or discount. Ask like you’ve done it a thousand (successful) times before, with the confidence and knowledge that they can grant your wish. If you make it seem natural, they’ll feel more casual and comfortable about helping you.

Here are some additional body language tips to get you enroute to your next travel discount or upgrade.

Nora Dunn is The Professional Hobo; a woman who sold everything in Canada in 2006, and has traveled full-time in a financially sustainable way ever since. She doesn’t sacrifice style however; with expertise in travel, personal finance, and lifestyle design, Nora gets the most bang for the least bucks. Follow her on Facebook or Twitter.