Port of Spain
A bustling and friendly city, Port of Spain is a great place to spend a couple of days and is the hub for the Trinidad's famous carnival.
The main shopping area is between Frederick Street and Charlotte Street, running south to Independence Square (Brian Lara Promenade). As well as the bricks-and-mortar shops, there are numerous stalls on the street selling everything from fruit to CDs.
In the evening Independence Square is full of locals liming - hanging around, chatting to their friends and sampling food from the stalls scattered throughout. Wandering through here is a great way to get a feel for what Trinidad is about.
...and several others
Many different styles are available.
A local flour and chick peas delicacy called Doubles (available all over the island, even just outside the airport). There are several stalls on Independence Square can get these for 3TT each - make sure to get their early though as they tend to sell out pretty quickly.
American fast food chains like Kentucky Fried Chicken (KFC) and Burger King (try the totally local fast food chain Royal Castle!)
To eateries like - Benihana and many others available at Trincity Mall, 15 mins from Piarco Airport
To restaurants at hotels like The Trinidad Hilton to the only revolving restaurant in the Caribbean at the Crowne Plaza.
Just remember Trinidadians and Tobagonians like foods more spicy than North Americans or Europeans! Be careful with the hot sauce, because it is really hot!
Beer is a little expensive, priced around 9 TT (1.5 USD) at grocery stores and 15 TT (2.5 USD) at restaurants for a 275mL bottle.
Trinidad has a bad reputation (it has a shocking high murder rate), but if you are sensible and stick to the main areas, you shouldn't have a problem and will find the locals incredibly friendly. Avoid any ostentatious display of wealth, and don't wander down dark backstreets at night on your own, and you shouldn't experience any problems at all.
Wear sunblock, since Trinidad is very close to the equator.