NEW YORK (CNN/Money.com) – Who's in the running for a $300 tip this holiday season?

Nannies, personal trainers and even dog walkers might possibly nab tips in the hundreds of dollars...though it's certainly not required.

"You tip the people who perform services for you year-round, who are there for you when you need them and whom you have a valuable relationship with," said Peter Post, director of the Emily Post Institute and author of Essential Manners for Couples.

Linda Sondik, a personal trainer at New York Sports Club, said that one woman who tipped her in the hundreds had set a difficult goal at the beginning of the summer and reached it by Christmas.

"It was really emotional for both of us," said Sondik, adding that when tips far exceed the norm, it's often because a relationship with a client has become very intimate.

Extraordinary holiday generosity is great, but etiquette experts emphasized that tipping isn't designed to put you in debt.

"Forget about what you ought to do. Do what you can, and do it in the nicest way you possibly can," Post said.

Tipping experts said, and tip recipients implied, that cash is the best way to say happy holidays.

Hilka Klinkenberg, founder of Etiquette International, once gave one of her doormen CDs because they had often discussed opera, while the other men received cash. "He looked at me crestfallen," she said. "Tipping is not a time to try and be original."

Whether we tip with a song or a grumble, handing over the envelope should be done graciously.

Klinkenberg said to also include a short note thanking the recipient for their hard work, and to give the tip in person whenever possible.

Other tipping tips include

• If you frequent a restaurant daily, it's a good idea to tip your regular waiter. An extra $5 in a card is a kind gesture at your regular lunch spot, while at the Four Seasons you could shell out $40-$50, plus similar amounts to the maitre d and captain.
• Don't forget the snowplow man. He comes when you're in a bind, every year, every time it snows.
• You don't have to give as much to the new hairdresser, doorman, etc. because you haven't forged a relationship with them yet.
• Alcohol is not recommended. Just because you may enjoy the extra splash of cheer, it might not be right for someone else.

Otherwise, when in doubt, follow the table below.