The first time I was on the Napa Valley Wine Train, I was about eighteen. A friend worked on the train, and he snuck me and another friend onto the caboose. We spent the day drinking beers (which were also snuck on) and waving to tourists. Though I think this is the best way to ride, the wine train has many other options. Unfortunately, they all require purchasing a ticket.
Four dining cars offer varying levels of investment. The gourmet express has two seatings, one on the way up to St. Helena, and one on the way back. A three-course lunch will run you $89 and a four-course dinner $97, both excluding wine. In the Vista Dome car, there is only one seating (meaning you get to keep your seat for the entire journey); a four-course lunch with a glass of sparkling wine is $119, and dinner with sparkling wine is $127. I have eaten on the train once and the food was great.
A more casual option is the Silverado Grill Car, which allows people to choose from an à la carte menu. Alternatively, you can ride the train ($49.50 for round trip ticket) and just drink. The wine tasting bar has over one hundred types of wine; five dollars will buy you four tastes. There are four parlor cars for lounging and a full bar in back.
In addition to a Friday Vintner’s Luncheons, there are a host of other themed dining excursions. Murder on the Wine Train Express includes a four-act play and four-course dinner for $135 per person. The Varietal Voyage focuses on one particular wine—say Merlot, Zinfandel, or Pinot Noir—and pairs this with a four course meal ($140 including wine). Alternatively, the Appellation Dinner pairs wine from a particular grape growing region, like Spain, Stags Leap, or France, with a four course meal ($150 including wine).
During the holidays, the wine train offers special events; a turkey dinner for Thanksgiving, a chance to see Yountville’s Fourth of July fireworks from your railcar. Since DUI’s are plentiful in the valley (“come to Napa on vacation; leave Napa on probation” is a favorite saying among the police) the wine train has a “Don’t Drink and Drive” New Year’s Eve celebration.

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