Theatre Archipelago showcases theatre from the Caribbean. Caribana, the Caribbean Carnival held every summer in Toronto, is the ultimate street theatre, so Theatre Archipelago believes it should have a presence there.

Caribana mainly focuses on ostentatious masquerade; what is called “pretty Mas” in Trinidad. It does not usually include traditional Trinidad Mas characters such as Jab Molassies or Ole Mas – a satirical form of mas that usually involves skits, wordplay and puns to portray social and political issues of the day. In the summer of 2011, Theatre Archipelago brought the J'ouvert tradition to the island Soul Festival at Harbourfront in Toronto with a presentation called Jouvay on the eve of the Scotia Bank Caribbean Carnival formerly known as Caribana.