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Most restaurants include a 10% service charge on the bill. In many cases, this is goes towards covering service staff overheads or is split equally between all waiters. If you really want to tip a particular waiter for his/her exceptional service, make sure to physically give them the cash or leave it on the tablewhere they can see it. Never add it into the bill or credit card slip.
It is also recommended that you tip if someone did something for you for free or really went out of their way like putting your luggage in your car or carrying something down to the beach for you or made your stay/tour really memorable. A typical tip in such a case could be between $5-$20 TT depending on the assistance provided.
Other services (such as hairdresser, grocery packers, gas station pump attendants) do not need to be tipped but if you want to you'll have to be your own guide - no one will offer how much is acceptable, it's totally up to you. Usually $5-$10 TT would be sufficient.
In Trinidad and Tobago, most taxis/maxi-taxis are shared with several passengers dropping off at different stops along fixed routes. As a rule you don't tip taxis at all. Tipping in this situation would draw unnecessary attention to yourself.
If you do happen to hire a private taxi , tipping is at your discretion. However, just remember private taxis charge a premium, so only tip if the driver really provides an outstanding level of service.
Like in anywhere else, a few dollars, each round, for the bartender will get you better service.
Unfortunately the social welfare system in Trinidad & Tobago is not sufficiently developed. Little children (usually on the beach) selling fruit could be given $1-$2 TT even if you don't buy anything from them. Giving money to adult vagrants begging for money should not be encouraged at all.