Access from Tokyo
By car:
approximately 3.5 hrs.
From Tokyo, take the Tomei Expressway about 30 minutes to the Atsugi Interchange and head towards Odawara on the Atsugi Highway. After about 30 minutes, you will reach Odawara. From Odawara, take the Manazuru Highway to Atami and then R135 to Ito (about an hour). From Ito, drive down R136 for about an hour to Shimoda. Stay on the 136 and drive through Shimoda Town, once about 5 minutes outside of town you will see a sign to Ohama. Turn left and go straight. Soon after you will see a bar called 70s Bronx on your left, about 200 meters past the 70s Bronx you will see tabi-tabi guesthouse on your right.
By train:
Izukyu-Shimoda station is the last stop on the Izukyu train line and Shimoda is as far south as you can go by train on the Izu Peninsula.
From Tokyo Station, Shinjuku Station, Ikebukuro Station: the Odoriko train makes a few runs daily via the JR Tokaido Main Line. A one-way trip takes about 2.5 hours and a costs ¥5890 one way. Holders of the national Japan Rail Pass will have to pay only ¥2070 each way to travel over the Izukyu Railway, but if you have a JR East Rail Pass, the entire journey is fully covered. Check here for the Odoriko Schedule.
If you want to save some money local trains take slightly longer but are quite a bit cheaper (¥3780). From Tokyo you can take the JR Tokaido line to Atami in about 100 minutes and costs 1890 yen. From Shinjuku you can take the Odakyu line to Odawara and transfer to the JR Tokaido Line there. The whole journey to Atami would take more than two hours but cost only 1250 yen.
From Atami you would have to change to the Izukyu line bound for Izukyu Shimoda.
You can check all train schedules here:
For all your public transportation questions (schedules, prices, busses) I highly recommend calling the super friendly people at the JR East English Information Telephone Line:
050-2016-1603
from Izukyu Shimoda Station to tabi-tabi Guesthouse you can take a taxi or a bus from outside the station