The easiest way to get to Shimoda is by Odoriko Super Express train. Some of the trains are called Super View Odoriko because they have raised floors and windows that extend to the ceiling so you can enjoy views of the shimmering ocean and the lush landscapes of the Izu peninsula along the way. The journey takes approximately 3 hours and costs about ¥6500 from Shinjuku (with cheaper fares and travel times from other departure stations). Below is a list of departures times. There are other departure stations like Shinagawa, Ikebukuro, and Yokohama. For a complete timetable you can check the JR website here. You can also call the super friendly folks at the JR East English info line at:

050-2016-1603

Shinjuku Station - Izukyu Shimoda Departures:

8:30  /  9:25

Tokyo  Station -  Izukyu Shimoda Departures:

7:30  /  8:00  /  9:00  /  10:00  /  10:30  /  11:00  /  11:30  /  12:00  /  13:00  /  13:30  /  14:00  /  14:30  /  15:30

***Please note, the name of the station you want to get off at is Izukyu Shimoda Station. If you use Hyperderia or Jorudan to search for train schedules and fares, you must use "Izukyu Shimoda" as your destination point. There are other towns and stations called Shimoda in Japan.

****One more note, if you are using another train route, and are transfering in Ito or Atami, take care NOT to board a train bound for "Shimada" (with 2 A's), be sure to look for a train bound for Izukyu Shimoda.