Like its cousin beer train, the wine train (or wine densha) event put on yearly by the small private Gakunan Tetsudo train line is pretty special. Buy a ticket for about 2500 yen and ride the train to the end of the line and back (a total of about one hour) and drink all the wine you can. There are various kinds of wines on board, including a selection of nearby Yamanashi wines. And you shouldn't feel ashamed of keeping your glass full either. Everyone will be trying to get as much value for their money as possible and swaying by the end of the ride.
Like beer train, wine train is a good chance to talk with drunk locals and get your picture taken a lot and have an all round good time. It starts off and returns to JR Yoshiwara Station. Make sure to walk over to the Gakunan Tetsudo side of the station. Making a reservation for your party is very much recommended as tickets tend to sell out very quickly. While beer train takes place in summer, wine train is a winter event (February). Contact the Gakunan Tetsudo company for more information and walk with your own snacks.