The main aim of any Entertainment Area is to satisfy your pirates' needs as fast as possible in order to send them out to cruise regularly. You should situate your Entertainment around the docks as this is where the majority of Pirates will come from and return to. Remember that all entertainment structures emanate anarchy so avoid placing primary industries too near the district and place watchtowers or fear decors to keep captives in line.
An important rule of thumb is to have at least four Wench & Masseuse houses for every Smuggler's Dive. Companionship is usually the lowest satisfied need so it's important to make sure there are plenty of wench houses and maybe a few Brothels, which are larger, require more wood, but provide for 5 pirates at a maintenance cost of 2 per month and provide a bonus in satisfaction when supplied with cigars.
One Animal Pit for every two Smuggler's Dives seems to be sufficient, where both are rarely at full capacity.
Every pirate rank away from the target range who uses the building experiences a 10% decrease in satisfaction. In the early part of any game all your Pirates will be Rank 1 or 2. So there is no need for any of the higher quality entertainment buldings. By rotating what pirates are sent on cruises - by periodically firing the crew of a ship then letting it fill back up - you can even out the ranks of the pirates. The basic quality buildings should be sufficient for most of the game, as you can raise the rank ranges of one or two to satisfy the higher ranking pirates. It's not particularly efficient to exclusively cater for a high ranking Captain as space is usually limited.
One Smuggler's Dive and one Animal Pit, surrounded by 4 or 5 Wench & Masseuse houses is a basic layout that can be replicated side by side, or at each dock, if they are far apart.
One Smuggler's Dive is roughly sufficient for 20 Pirates.
Wealthy captives, on the other hand, are treated like Pirate Rank 9 and are not really satisfied with less than the highest entertainment structues (i.e. Inns, Courtesan & Spas, and Casinos) set at maximum satisfaction rank. Once you get them, consider building those establishments, particularly an Inn to provide the means for them to sleep. Also set their price range to Gouge Em; pirates generally don't visit them too often and Wealthy Captives have unlimited money and their ransom will increase by the money they spend there.