Yes, travel insurance is worth carrying for a trip to Port of Spain, and the reasons shift depending on when you visit. Trinidad's Carnival, centered on the Queen's Park Savannah and the streets around it, draws enormous crowds each February or March, and that density brings its own genuine risk of theft, lost belongings, and crowd-related injury that a routine city trip does not. Outside Carnival season, Port of Spain functions as a fairly ordinary Caribbean capital, and the honest case for coverage becomes standard medical and trip-disruption protection rather than anything dramatic.
Port of Spain has private clinics and hospitals that handle a wide range of care, but treatment at private facilities can be costly for a visitor without local coverage, and public system capacity is uneven. Check whether your policy pays providers directly or requires you to pay first and claim later, since covering private-facility costs upfront in an unfamiliar system can be a real burden if something goes wrong during a busy Carnival week.
Trinidad sits further south than most of the Caribbean, below the main hurricane belt that runs through the northern islands, so direct hurricane strikes are comparatively rare here - a genuine bit of nuance worth knowing rather than a reason to skip coverage. The wider Atlantic hurricane season, roughly June through November, can still bring heavy rain and flooding even without a direct hit, and Carnival itself falls well outside that window entirely.
Keep any clinic invoices, police reports for theft or crowd incidents, and receipts for lost or damaged belongings, since Carnival-season claims often involve exactly these. Check whether your existing health cover extends abroad and specifically to Trinidad and Tobago before assuming it does, and confirm your policy's documentation requirements before you travel rather than after a busy Carnival crowd has already dispersed.