Friends are the best way to raise funds. With the help of your crew, your flag, or your hearties you can raise extra pieces of eight much faster than you can on your own.
Run a pillage or flotilla attack and ask everyone aboard to donate what they make back into the hold. You can do the same with an Atlantis or Cursed Isle attack as well. Make sure you announce this before you start and several times during the voyage.
Ask your crewmates and flaggies to donate stuff to be auctioned. This can include clothes, furniture, or trinkets or other in-game items. Ask an avatar artist to donate a free avatar. You can even auction yourself (usually called a "slave" auction, the winner gets the services of the pirate "on sale" for a specified period of time.)
Pool your money with a partner and wager on various team parlor games (swordfighting, rumble, and spades).
Shopkeeping
Interface for opening a bazaar stall.
Anyone can open their own stall in a bazaar with some amount of PoE, which is determined by the type of stall, the population of the island, and the island's tax rate. On subscriptionoceans, a pirate must be a subscriber to open a stall, on doubloon oceans, an additional 10 doubloons are required to open a stall.
To open a shoppe you must first obtain a deed, usually from the governor of the island. All shoppes start off as construction site, which may only be placed by the governor of the island. Once the construction site is put up the governor immediately recieves the deed to the construction site, the deed may be traded straight away or the governor may keep it. After a shoppe is finished being built it may then start trading and rent will be required from this point onwards. As the space on an island is limited, shoppes are often sold for large sums.