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Most important: Rent a car when visiting. The island isn't suited for exploration by foot. The distance between places of interest can be great and the whole island is full of steep slopes. I rented an electric bike and would only recommend it to people who have the explicit goal of biking. It is worth noting that you can reach the island by ferry AND plane. Taking the ferry has three sleeping options - I STRONGLY advise against anything but the most expensive one. I don't know if the first class is good, I just know that the other two are a surefire way to a bad night. Taking the plane is about as expensive or even cheaper than first class on the ferry, only takes an hour, and isn't a 10 hour ship ride. IF you take the ship to the island, I strongly recommend taking the plane back. The ferry leaves for Hachjiojima at 22:30 and arrives at 9:00 - an overnight trip. But it leaves the island at 9:30 and arrives in Tokyo at ~20:00, meaning you lose an entire day. Regarding the island itself: I think some of the highlights are climbing Hachijofuji and exploring the abandoned Royal Hotel. Both are manageable within a day. Depending on the weather, Hachijo has a beautiful night sky - it's not called Dark Sky Island for nothing. Other things worth doing are visiting Plant Park in the west of the island and exploring the southern side. There are some nice onsen experiences to be had in the south, but not all of them are open at all times. Planning a trip of two days, - arrival by ferry at 9 AM, doing things, spending a night, doing things and leaving by plane at 5 PM, - seems prudent choice. It's a subtropical island, which you might want to keep in mind if you plan on visiting in summer.