2 guys Patrick and Gabe from Yugawara Sharehouse/The Other House alliance made a video about traveling using the train from Jyogasaki to Shimoda.
They also a used the Izukyu-Line 1 day pass, which is a ticket you can get on and off for 1200yen, only availiable to foreign tourists in Japan. (I envy you guys!)
You can also see how Gabe was able to get his phone back with a help from a very kind Izukyu line staff member.
Check here for Izukyu line 1 day and 2 day passes.
Check out what a day for you might look like when you use the 1 day pass (Trip in between Shimoda and Jyogasaki Station).
Video by Gabe D.