Dear Roxy: How Do I Get An Upgrade, or Just A Better Hotel Room?

Dear Roxy: How Do I Get An Upgrade, or Just A Better Hotel Room?

Dear Roxy is Sharing Travel Experience’s biweekly columnist answering your questions about getting the best value and best experiences during your next hotel stay.

Today, Roxy is talking the topic of upgrades. Got a hotel question? Just ask Roxy.


hotel upgrades
Everybody loves a room with a better view.

Dear Roxy,

Loving this column, so fun! While we’ve signed up for points programs and membership points (mostly to rack up the credit card points for free rooms), we don’t travel near enough for any fancy upgrades or special perks except the occasional free drink in the bar. Any suggestions on how us regular folk can get upgraded – I’m not even sure what to say? Is that something to try in advance or just on check-in?   What about just getting better hotel room (better views, more space, etc.)?

– Lisa from Florence [ the Kentucky one, not the Italian one 🙁 ]

Ahhh, I love Kentucky, Lisa, don’t sell your state short!  

Most people make a crucial mistake when it comes to seeking upgrades.

They rub the reservationist the wrong way with an in-your-face demand for upgrades because they are so special, you know, they think they’re a big deal.  All that will get you is an eye-roll and a room by the elevator/ice machine!  But if you called and treated the clerk like a person…well, now you’re talking.  Explain your desire for the upgrade (maybe it’s a special day, showing someone their beautiful city for the first time, etc.) and ask them if there are options available for upgrade.  If it’s a slow day they may do it free, better to have a super happy guest in a room that would’ve been otherwise empty.  Or sometimes hotels offer an upgrade for a small fee like $10.  I know, it’s ten bucks, but it makes them feel like they’re getting something, too.

The key is building that relationship with the person on the phone.  Asking them what their opinion is on rooms or recommendations of things in their city goes a long way.  And if they send you to places they like to go (instead of where all the tourists get sent) you’ll probably have a great time!

Dear Roxy,

I wanted to ask you…. I normally just book my hotels straight up, without any of the fancy packages or combined offers (since they usually have things I wouldn’t use). However, sometimes it would be nice to get a comp’ed breakfast when that’s not included, or to get a slight discount for on-site restaurants when they’re local and interesting (not often the case, I know). Since I’m not a high rolling traveler, is there an art to getting perks and comps? I’m not asking for much, oversized hotel suites don’t do a lot for me, just the little things here and there.

– Alice in Toronto

Greetings, Canada, my nearby neighbor, eh!  Sometimes when hotels put together packages it enables you to do/get things for less than it would cost independently.  So even if you didn’t use all the parts of the package, it may still be worthwhile to book that way if you use most of the items.  But a few questions on your part can help you out:

  • Ask if breakfast is included either at a continental setting or in the hotel’s establishment.  Sometimes the clerks have the ability to give out certificates or discounts for this if you ask nicely!
  • Inquire about any hosted happy hours—these are a good source for a couple free cocktails and apps.  And who doesn’t love free cocktails?!
  • Check if the hotel has any discounts with local restaurants.  It is quite common for hotels and restaurants to offer each other’s customers a discount rate of 10-20% off.  That being said, keep in mind that these dining facilities are probably higher end to start with.

If you want a great experience at a better value, do what I encouraged Lisa to do, ask the folks at the desk where they like to go.  If you have a particular type of food or certain meal in mind, tell them.  No doubt they have some great ideas for you; after all, they like to eat, too!

Dear Roxy: How Do I Get An Upgrade, or Just A Better Hotel Room?


Roxanne ("Roxy") is the easily distracted, multi-tasking right brain of Fresh Air Lodging. After twenty plus years on the front lines of the hotel industry, she is now in search of socially responsible hotels and other businesses.

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