Located 297 kilometers from Tokyo, Hachijojima can be reached by boat from Tokyo's Takeshiba Pier in about 10 hours. I recommend, however, taking the short 50 minute plane ride from Haneda.
I recently visited Hachijojima because the islands of Tokyo are very interested in attracting foreign tourists. I can't say that the island is very 'English-friendly', but the kindness of the local population more than makes up for it. Everyone went out of their way to help and/or entertain us.
Then we headed out to this gorgeous 'lookout' at the Fureai Farm. There is a small rundown building here with a few tables inside and a vending machine filled with tasty locally produced milk. Walk down to the end of this path for a gorgeous view of the rest of the island. Along the way you'll pass some cows, each with its own ear-name tag.
The next stop was the Ki-hachijo Dyeing facility. Silk, woven with distinctive black, brown, and yellow colors, was originally produced in order to pay the island's taxes, which continued until the Edo era. The workers here are all very young, and it is interesting to see them work. There is a detailed (and interesting)presentation of the process and history, but again, without an interpreter, you'll need to be pretty good at Japanese to understand. Unfortunately, this building is also full of clutter.
The hotel has a golf course nearby, a 'mini-golf' course right beside the pool, a very nice indoor onsen, and a short walkway that takes you along the lava-formed rocky coastline to a private bench - perfect for watching the crashing waves.
Depending on what meals you choose and how many people are in your room, the price per person is between 7,000 and 20,000 yen.
Here is a helpful English website for the island: http://www.8jyo.jp/en/index.html
Here is a pub that is extremely foreigner friendly. Their website is really informative, and they even offer tours in English! http://www.hachijo.net/index.html
Here is another hotel on the island, the Hachijo Sea-Park Resort. It has a really nice English website.
http://www.pearlcity.co.jp/hachijo/English/E_top/E_top.html
And for the budget conscious, the Galaxy Guest House also has a good English website. http://www.geocities.jp/paradoisejapan/ Rooms with no meals start at 4000 yen!
Public transportation on the island (bus) is very infrequent. I highly recommend bringing a bicycle or renting a scooter or car. Although their website is only in Japanese, Mobile Renta-car can take phone reservations in English. http://www1.ocn.ne.jp/~mobil/ Prices are really reasonable.
Although I don't feel that this island has any special features to distinguish it from other Japanese islands, I like that it is very interested in attracting foreigners. If you are living in Tokyo and you really want to get away from human beings - this is a good choice. With only a couple of flights a day on smaller aircraft, and a population of only 8,500, anywhere you go will be extremely quiet. Everywhere we went, we were the only people there!
If you are a nature lover and like to walk, just wandering around the island would be a great escape. Here is a really good blog about the island: http://chibaraki.wordpress.com/2009/12/30/on-a-deserted-tropical-island-with-palm-trees-in-tokyo/