Preparing For Your Trip

When planning your vacation, I hope you develop a budget: I hope you identify how you will travel to your destination, where you will stay once you get there, which attractions you wish to visit, where you will dine out, any other incidentals expenses you will incur such as ground transportation and parking and how much all of that will cost. Then as your trip progresses, I hope you reconcile your expenses against your budget and ensure you are using the credit card that gives you the best redemption for your spend-categories. Easy!

But we forgot a budget: The Hotel Upgrade Budget – $20.00.

Tipping at Check-In

Though it may seem cliché, I have had incredible success with tipping at check-in over the years. In fact, I’ve only been denied ONCE because the hotel truly had no way to upgrade me and refused to accept my tip as a result. Every other time I’ve tipped $20 at check-in, I have received room upgrades and other perks that I would not have otherwise. $20 may seem like a steep tip, but while it may be generous, it is a small price to pay for an enhanced experience on your vacation.


The last thing you want to do is be awkward during this interaction. Execution is key: Every time you check-in to a hotel, you are required to provide a credit card for incidentals and a deposit. Fold the $20 numbers-up and hand the folded bill over with your credit card as you kindly ask the staff member: “Are there any room upgrades available today?” Be prepared to tip them that $20 just for looking without receiving an upgrade: Being entitled will get you nowhere, and you are owed nothing in exchange for the request.

What’s $20 Worth?

During our recent trip to New York City, I made this request and not only received a suite upgrade ($70/night value) but two drink tickets for the lobby bar ($30 value). Because we stayed at an independent property, I did not have elite status with the property chain and the $20 investment in our stay made all the difference. Though suite upgrades are often offered (based on availability) to us as elite members with Hilton, Marriott, SPG, IHG, etc., nothing is guaranteed. And your willingness to be generous in the uncertainty not only makes a positive difference for the staff member, it increases your chances that they will make an otherwise-difficult accommodation available to you.

Calculated Risk

Especially when you have an extended-stay planned, $20 can make a big impact to the person behind the counter while making very little impact on your vacation budget. Remember: You’re not entitled to anything for asking and acting otherwise will get you nowhere. But good things come to those who put good out there and the chances of your $20 being worthless is unlikely. So add $20 to your next vacation budget, and bring it in the form of a crisp bill ready for check-in. Worst case, you will be gratuitous.