Getting to Hakone is easy; the only real decision is the pass. From Shinjuku, the Odakyu line takes you to Hakone-Yumoto, the gateway to the loop. Here's the cleanest way in and why almost everyone should buy the Hakone Free Pass before boarding.
Buy it at the Odakyu counter in Shinjuku. It bundles the round-trip from Tokyo with every leg of the loop — Tozan railway, cablecar, ropeway, pirate ship and local buses — so you tap through everything and never queue for tickets. For the standard loop it usually pays for itself by the ropeway, and the 2-day version costs only a little more if you stay over.
Clockwise, early, crowd-free — the route that works.
Open the day-trip routeTake the Odakyu Romancecar from Shinjuku to Hakone-Yumoto (~85 min) with a reserved seat, or the regular express with one transfer at Odawara. From Tokyo Station, Shinkansen to Odawara then the Tozan line.
For the standard loop, almost always yes — it covers the round trip plus the railway, cablecar, ropeway, boat and buses, and saves you queuing for tickets all day.
About 85 minutes from Shinjuku to Hakone-Yumoto by Romancecar; the loop legs add up from there.