7 Ways to Tip Like a Boss During Your Next Hotel Stay

Why is it tipping can give even the most seasoned traveler sweaty palms? Feeling the frozen stare of the bellman as you fumble with your wallet, wondering if the bills you’ve handed over are appropriate...it can make for an awkward start to any trip. But tipping doesn’t have to give you heart palpitations and we're here to help you out.

To get all the best tips on tipping, we turned to two pros -- Sean Murphy, Editor in Chief of Jetsetter.com, a leading site for luxury hotels and experiences, and Jacob Tomsky, author of the hotel tell-all memoir “Heads in Beds.” Here are their personal guidelines for tipping like a boss.

1. Tip early.

Photo: StockMonkeys.com on Flickr

Do you wait until all services have been rendered before you dole out tips? Rookie mistake. “In almost every situation, tipping up front is the best way to go,” Tomsky says. “Get that out of the way, right away, and watch the stress drain from the situation.” 

Murphy agrees. “I usually tip early in my stay,” he says. “I often give the first person that is in a position to help me a substantial gratuity and make it clear I will appreciate their best efforts on my behalf.”

2. Be clear and confident.

No need to fumble, mumble, or be shy when it comes to tipping. “I put the gratuity in the palm of my hand and offer a firm handshake while making eye contact. This way they know I appreciate their effort, but I am not making a spectacle or public declaration of the transaction,” Murphy says. 

And don’t worry about a tip being inappropriate. “Worst-case scenario, they refuse politely and still consider you a wonderful person for even trying,” Tomsky says. But in most cases, tipping is warmly welcomed. “Embrace it! Loud and proud. It is a beautiful gesture. No reason on earth to be awkward," Tomsky assures. "Just a simple ‘Here this is for you,’ and it’s all over.” 

3. Always tip housekeeping.

Friendly housekeeping staff at The Equus

If there’s one job that should always, always receive a tip, it’s this. “I’ve done housekeeping, and it is HARD,” Tomsky says. Murphy adds that housekeeping is “meant to have an almost invisible personal presence, but their work is the most visibly recognizable.” 

So if the hotel leaves envelopes for tips, be sure to use them. “Money left on a night table is ambiguous. Is it a tip? Or am I an absent-minded fool who left his cash behind?” Murphy says. “A five on the desk might look like a five on the desk you expect to see there when you return,” Tomsky adds. “The addressed and sealed envelope is key.”

4. Tip on the level of service, not the luxury of the hotel.

It’s easy to be swayed by luxurious surroundings -- or be dismissive of value hotels -- but the truth is, good service requires the same amount of effort no matter the level of hotel, and thus should always be rewarded. “I usually evaluate all hotel staff based on the quality of their service, not the cost of the hotel,” Murphy says. In other words, even if you’re staying in a budget motel by the highway, you should still leave out money for housekeeping, because your sheets don’t change themselves.

5. Throw a little cash on top of the room service tab.

Photo: Chris Goldberg on Flickr

We know. Room service is already super pricey. And if there’s an added gratuity on top, you may feel you’ve paid your share. But if you can, pass along a few dollars in cash in addition. After all, that added gratuity goes onto a paycheck that’s taxed, which means it can “come out pretty paltry on the other end,” Tomsky says. “A few dollars in the pocket can mean the world to them.” 

And even if you’re not inclined to tip above that 20 percent, consider adding a bit more during certain times of the day or for certain room service orders. “If the delivery is particularly late at night or involves chocolate and/or Champagne, I’ll tip a few bucks above the included gratuity,” Murphy says.

6. Study the norm, and go a little above.

The American Hotel and Lodging Association puts out a set of “Gratuity Guidelines,” but both of our experts felt their suggestions were a tad too skimpy. “These are pretty much on par with what is average,” Murphy says. But he’s not content to settle for average. “I’ll consistently give more to individuals who remember my name and what I like, treat my kids well, or introduce me to an awesome bar, restaurant, view, local shop, or something I had no idea existed.” Tomsky also believes in bumping up these amounts. “Honestly, on down the list, I’d make every $1 into $2,” he says. “But this list is a pretty decent starting point.”

7. Give thanks, and get thanks.

Who doesn't want a dose of good karma?

Ultimately, tipping is about karma. “Hospitality is hard, and it’s the best way to show any hotel employee you understand that universal truth,” Tomsky says. Sometimes that karma comes full circle. A well-placed tip can open doors...literally. “Twice, 100 Hong Kong dollars (approximately $10 US) at check-in got me upgraded to deluxe rooms on top floors,” Tomsky adds. 

But ultimately tipping is about showing appreciation. “Giving gives us pleasure. Knowing this, I usually over tip. This way everyone walks away happy -- except my accountant,” Murphy says.

Oyster’s General Guidelines for Tipping:

  • Valet/Parking Attendant: $2 to $5
  • Shuttle driver: $2
  • Door Staff: $2 to $5 for hailing cabs (especially in poor weather)
  • Bellman: $2/bag ($5 for especially cumbersome bags)
  • Front Desk: $5 to $10 (optional, but encouraged)
  • Concierge: $20
  • Housekeeping: $5/day
  • Room service: 20% of the tab (a few extra dollars in cash if tip is automatically charged)
  • Delivery of items to room: $2 to $5
  • Pool or beach attendant: $5
  • Waitstaff busing buffets: $5

*Based on expert feedback.

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