Legend has it, the word "tip" itself came years ago from a pub owner who used the acronym on a box "To Insure Promptness." In that spirit, tipping should be thought of first and foremost as a reward for prompt and attentive service.
In reality, tipping etiquette has evolved into a secret subculture with hidden expectations that aren't always well understood by travelers. Break the secret code behind tipping etiquette. For a guide to who to tip (and how much), check the Hotel Tipping Guide.
Time Your Tipping
Depending on the timing, tipping can be a reward for good service rendered, or a subtle bribe. If you are using the service of one person repeatedly throughout your trip (say, a doorman) feel free to tip all at once at the end of your stay. If, however, you would like to ensure special service throughout your stay (say, from the concierge), a larger tip up front is a good idea. Tipping etiquette says either is acceptable.
Keep Bills Handy For Tipping
Keep several one dollar bills handy in an accessible pocket. You don't want to be digging for them when you're juggling luggage. Keep the bills neatly folded in groups of one or two bills.
Don't Ask For Change
According to tipping etiquette, it creates a very awkward situation to ask for change from the person you are tipping. If for some reason you don't have a tip ready, it's better to skip it, particularly if you can get change from somewhere else and return with your tip at some point in the future.
Know Your Tipping Tendencies
Be aware of your own unconscious tipping tendencies. Studies show women tend to tip men more generously (and men tip women better). Tipping goes up universally when the weather is good, lower when it is not. Attractive women earn higher tips, as do attentive men who don't make mistakes.
Know the Tipping Policy
Increasingly, higher-end hotels are instituting "no tipping policies" that include gratuities in the price of the room. Some, particularly resorts, are charging a daily fee that covers all gratuities. However, if you sign up for outside excursions or tours (even those that don't cost extra), chances are the drivers and/or the tour guides will expect tips. Ask when you book.
Bed and Breakfast Tipping Etiquette
In general, tipping etiquette dictates that business owners are not given tips. Most B&Bs fall under that category, and indeed, most have "no tipping" policies in place. If you are in doubt, ask about their tipping policy when you book your room. (If the housekeeping staff is not part of the family, do tip them as you would in a hotel.)
Tipping Is Never Required
It may be expected in many situations, but tipping is never required. Tipping hotel staff and drivers should be at your discretion, and should be thought of as a reward for excellent service. Don't feel obligated to give a tip if the service given was sub-par. On the other hand, consider giving a larger tip for those who go out of their way to provide personalized or stand-out service. Although it is not required, tipping etiquette says that unless service was severely lacking in some way, do give a tip of some sort (or at least a smile and a thank you).
Tipping Etiquette Varies Worldwide
These tipping guidelines are for the United States only. Expectations (and tipping amounts) can vary quite a bit from country to country. Check a travel guide for the particular country you will be visiting for the proper international tipping etiquette.
Now that you know the secrets behind tipping etiquette, check the Hotel Tipping Guide for who to tip at a hotel (and how much to tip them).