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.
Westerly view from Botanic gardens at Port of Spain
...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.
Angie's Bed and Breakfast, St.Ann's Road, St.Ann's,Port of Spain, ☎ 868 627 0710. From $60.
Carnetta's House & Inn, 99 Saddle Road, Maraval, Port of Spain, (email@example.com, fax: 868 628 7717), . From $70.
Copper Kettle Grille, 66 Edward Street, Port Of Spain, ☎ 868 625 4381. From $31.
D Islands Inn, 7 Anderson Street, St. James, . Private and secure.
Par May Las Inn, 53 Picton Street, Newtown,, ☎ 868 628 2008 (fax: 868 628 4707), . From $56.
S&D Guesthouse, 4 La Puerta Court, Diego Martin, Port of Spain, ☎ 868 684 2494. From $40.
Samise Villa Bed & Breakfast, 47 St. Anns Road, St. Anns, Port of Spain, ☎ 868 682 9589 (firstname.lastname@example.org, fax: 868 369 3836), . From $35.
Tony's Guest House, Papnis Drive, Petit Valley, ☎ 868 763 4230 (fax: 868 632 0440). From $30.
Courtyard by Marriott Port of Spain A favorite among business and leisure travelers, the Courtyard Port of Spain offers spacious accommodations, free high-speed Internet, a full-service restaurant and other convenient amenities and services. Invaders Bay, Audrey Jeffers Highway - Reservations: 1 868 627 5555 
Hilton Trinidad & Conference Center. Lady Young Road, Port of Spain, Trinidad. Tel: 1-868-624-3211.. Newly renovated, this hotel boasts hosting President Barack Obama, Secretary of State Hillary Clinton and the whole US delegation during the 2009 Summit of the Americas.
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.