Just for anybodys general info, if you want to finish the poker or black jack quests more quickly, go to Cuba where you may already have TP access (depending on who you're doing the quest for). If you happen to have tp access to Padre del Fuego (or if you dont mind sailing there) thats a great place to win big, too (or lose big, but they don't count your losses in the quests), and you can easily win the 150 in one or two hands.
In Cuba the pub is unmarked (it is the shack with steps at the front, middle of the island), but there is both a black jack and poker table there, where the pots are bigger than in Tortuga or PR. Most people have no idea there's even a pub there, so its easy to find an empty seat.