Arrive at a hotel, especially with a date on your arm, and prepare to be flummoxed -- your door-opening skills will be called into question by a man your father's age, another able-bodied guy'll offer to roll your luggage to the elevator, and the person who holds the keys to your castle (for the night) will hi-to-bye you in thirty seconds flat. So what's the way to a hotelier's heart? How can you make the most of your interactions with hospitality gatekeepers? After years in the industry, Jacob Tomsky wrote a tell-all memoir called Heads in Beds, and sits with Thrillist Travel to give some top-line tipping advice.
Thrillist Travel: I walk into a hotel with my girl and want to make a good impression, so we’re looked after. Who should I tip, and what might it get me?
Short answer here is tip everyone, if you can. It never, ever hurts. But let's break it down by department...
Valet: Tipping the valet might not make you look that good, but it'll keep your car looking good. I worked valet for a while; these dudes don't care. If you get a chance, drop a dollar or two on the parker so, at least, as they pull off in your car, they've got you and your currently pristine vehicle on their mind.
Doorman: These guys run the streets. They know the limo drivers. They know the lady who lives around the corner and walks her dog at exactly 11:15a. They know the scrubby homeless man who passes back and forth every day, dragging a garbage bag full of garbage possessions. They also know the best places to eat -- places the concierge won't tell you about. Most likely born and raised in the city, doormen can be your ambassador to streets. A nice $10 or $20 upon first meeting will put you in his good books, and that's definitely where you want to be.
Front Desk: Ready to be let in on the biggest secret in the hotel business? Tip the front desk. I worked this gig for YEARS -- we know every room in the property. And all that typing? That's us, choosing which room YOU are going to get. So, at the very least, be kind. Understand the important nature of the check-in process. And, yes, drop a $20; that can get you upgraded, comp'd amenities (including wine and fruit), late check-outs, and more. We deal with 300+ guests a day, so someone's getting a bad room. Be kind, generous, or both, and it sure as hell won't be you.
Bellman: These are some of the coolest cats on staff. They are the guys you'd want to be drinking with. One long night hanging with a bellman, and you'll know more about the city you're visiting than people who've lived there for years. They pay their rent with tips, so it's important to try and provide them with $2 a bag, but nothing shorter than a five-spot. These guys are also friends with the front desk, so having a bellman on your side means you have the front desk on your side as well.
Concierge: This is a difficult crew, so be a bit wary. They might have plans for you that're tailored to their own kick-backs rather than locations you'll love. That said, want court-side seats at tonight's game? A last-minute rez at a hot new restaurant? You're gonna have to go through them. And it's going to cost a $20 (to start).
Housekeeping: Wanna experience some seriously hard work? Try to clean ten suites a day, for five days. That'll have you tipping these ladies just because they deserve it. And they have access to AMENITIES; slippers, shoe horns, lint rollers, and more. A nice $10 or $20, in a envelope addressed to housekeeping, left in your room at the very start of your stay, is a kind thing to do. And if you see them in the hallway or entering/ exiting your room, be sure to thank them for their hard work.
Room Service: There's not much to be gained by over-tipping here. The gratuity's most likely added to the bill already, as well as a space for you to add more. However, room service is a dying art. So take advantage while you still can; the ability to enjoy fine dining in the privacy of your hotel room might not be around forever.
Thrillist Travel: How does one do the tipping dance? Do I cup it in a handshake like a freshman after a dime-bag?
Not necessary. Tipping, at its core, is an act of kindness -- another secret: no one, in the history of gratuity-giving, has ever looked bad from tipping. You look awesome, generous, and like the guy everyone wants to know. Employees will treat you with deference and you'll be a loved and respected guest. Own it! Throw a little money; even if it's refused, staff will still watch you walk off and think, "That was nice; he's a great guy. Too bad my manager was watching..."
Thrillist Travel: Now that I’m settled in my upgraded room with my comp’d wine and a few new friends in the lobby, what can I skim for free from the mini-bar?
Well, um, all of it? In my years in the industry I've learned that the mini-bar is the most disputed charge on any bill. People, all day, claim they've never touched it; some of them never actually did, yet received errant charges. Some of them touched it all over, but will have the charges removed anyway. The mark-up on the mini-bar is absurd and, even though it seems like, with a little disputing, you're getting $50 removed from your bill for mentioning something at check-out, it's really about $6 in a hotel's loss in product when I have a line ten-deep trying to check-out before breakfast ends. You think I've got time to send someone up to check?
Want to know more secrets from the inside of the hotel industry? Available in paperback, Jacob Tomsky's Heads in Beds, is a hilarious account of life on the other side of the front desk that'll change the way you both book and behave come your next hotel stay.