Gold, silver, and jools

[Thenamir]

Originally Posted by ROTK, Many Partings

To Sam he gave a little bag of gold. ‘Almost the last drop of the Smaug vintage,’ he said.

A cursory search of FOTR regarding Bilbo's departure from the Shire did not turn up any mention of Bilbo carrying away anything like a chest full of cash, and even if he did it seems hard to imagine that Elrond was charging him room-and-board while he stayed at Rivendell.

It looks to me (and I am certainly open to correction) that he had pretty much spent of given it all away -- and a good portion of what he had left at the beginning of FotR was probably spent on the massive expenses to throw the Long-Expected Party. By the coronation of Aragorn, all he had left was a small bag of gold which, in his typical generous fashion, he gave to Samwise to help start his family.

Of course, he says "almost" the last drop, so perhaps he has a bit more laid by to pay for busfare to the Havens...