Treasure Island is supposed to be set in the 18th century, but we don't see any signs of this historical disjunction from the time it was written, except maybe that pirates seem marginally more believable in ye olde days than in the staid, boring 19th century. The key settings of Treasure Island don't truly belong to any particular era: Jim's ordinary life in the Admiral Benbow Inn – and his extraordinary experiences on Treasure Island – feel timeless. The only sense we get of when this novel might be taking place is from references to real men like Admiral Edward Hawke (1705-1781) and Admiral John Benbow (1653-1702), the namesake of Jim's family inn.
What's much more important to Treasure Island than time is place – which makes sense given that the title of the novel is one of its settings. The different settings of the novel reflect the different stages of its plot development. Obviously, the adventures Jim can have in the Admiral Benbow Inn are very different from those he will encounter on Treasure Island. The Admiral Benbow Inn is a homey space Jim shares with his mother and father. So long as his family life is intact, Jim is sheltered from adventure. Once his family life starts to change, however, adventure comes to find him in the form of Billy Bones, former first mate to pirate Captain Flint.
Billy Bones is only capable of causing such a ruckus in the Admiral Benbow Inn because Jim's father is dying. The Admiral Benbow Inn is like a symbol of Jim's family life: it's only when Jim's family starts to break down with his father's illness that the inn become vulnerable to ruffians like Billy Bones. And once Jim's father has died and the Inn has been attacked by pirates, Jim's original family life has forever been broken. Even though Squire Trelawney repairs the inn for Jim's mother, Jim's place in it has been lost: his mother hires an assistant, and Jim realizes suddenly:
I had thought up to that moment of the adventures before me, not at all of the home that I was leaving; and now at the sight of this clumsy stranger, who was to stay here in my place beside my mother, I had my first attack of tears. (7.14)
So the Admiral Benbow Inn represents family, home, and Jim's origins all at once – and in leaving it, Jim is also symbolically leaving a part of his childhood behind.
The first stop on Jim's voyage of adventure is the coastal city of Bristol, where he meets a range of people who are different from what he's used to. It's in Bristol that Jim sees Long John Silver's respectable public face as the owner of the "Spy-Glass," a kind of bar/restaurant. Seeing Long John Silver as a business owner and man about town, Jim is all the more likely to trust his gentlemanly exterior.
By moving from the Admiral Benbow Inn to the schooner ship Hispaniola, Jim is going from established English order to a new, less hierarchical social space that has pirates and gentlemen rubbing shoulders. It's only when Jim is in the less socially rigid space of the Hispaniola that he starts to realize that a brutal, ambitious pirate lies beneath Long John Silver's polite facade.
Let's consider the names of these settings: Admiral Benbow was a famous naval officer who died protecting English trading rights in the Caribbean. So he is on the side of rigid order and Englishness, where Jim starts out the novel. On the other hand, Hispaniola was Christopher Columbus's original name for the island that's home to today's Haiti and the Dominican Republic. Hispaniola has experienced wave after wave of European colonial fighting. Given multiple cultural influences from Native American, French, Spanish, and African cultures, Hispaniola symbolizes the violent, varied cultural history of the Caribbean. Once Jim leaves England, he is moving away from home and toward a more uncertain new world, symbolized by the name of his ship, the Hispaniola.
We've covered the Admiral Benbow Inn and the Hispaniola – let's get to the destination everyone in the book is so eager to reach: the island. Captain Flint's chart calls this place Skeleton Island, and Jim calls it Treasure Island. These two names represent the two faces of this adventure: there are huge potential rewards at the end of the adventure (hence "treasure"), but everyone, pirate and gentleman alike, is at constant risk of death (hence "skeleton"). Treasure makes people do crazy things, and all you have to do is look at the death toll on this island to see the proof. More than two-thirds of the sailors aboard the Hispaniola in Chapter 9 aren't alive to sail back to England in Chapter 34.
One last point about the island and its relation to the novel's plot developments: it's during the characters' time on the island that we get the most alliances and double-crosses among them. Jim slips away to make an allegiance with marooned sailor Ben Gunn, an allegiance Doctor Livesey later joins. Abraham Gray ditches the rest of the crew to join Captain Smollett's party. Long John Silver starts out as the worst mutineer of all, only to find himself striking a deal with Jim Hawkins and Doctor Livesey to save his life once the rest of his pirates turn against him.
What's really fascinating about these plot twists is that we can find physical signs of the novel's shifting relationships on the island itself. Take the largest hill on the island, Spy-Glass Hill. That name reminds us of Long John Silver's bar back in Bristol (called the Spy-Glass), which suggests that he already knows more than anybody else about the island. But as Long John Silver starts to lose control of his pirate crew, the island's layout itself seems to change: the fort shifts hands from Doctor Livesey and the good guys to Long John Silver and the pirates. Why? Long John Silver has no idea. Even the treasure map stops being a reliable guide, since the pirates trace all its clues faithfully only to find a big hole where gold bars should be. As the situation shifts and changes, Long John Silver's initial, superior knowledge of Treasure Island dwindles, until eventually he's at the mercy of Doctor Livesey and Ben Gunn.