Isle of Wight
Isle of Wight is an island in the south of United Kingdom. It is great for hitchhiking. The roads are mostly small yet with plenty of traffic, and there aren't any big towns on the island. It is easy to get a lift. Simon hitched to Brading from the outskirts of Ryde every day after work for three months, and was normally picked up within a minute. There are no difficult places to hitchhike from on the island - just walk a little bit if it seems like noone is stopping, and no doubt someone will within a few minutes.
North towards Portsmouth, Southampton, the New Forest
Isle of Wight is linked to the mainland with ferries running to Portsmouth, Southampton, and Lymington. All of the car ferries are possible to hitch a lift on, as drivers pay for their vehicles and not per person.
The terminals on the island are each quite small, and if staff give any hassle when hitching inside the terminal it should be fine getting a lift from just outside the terminal too.
Fishbourne, which is closest to Ryde/anywhere on the east or south of the island, is halfway between Ryde and Newport, and easy to hitch to. The ferries go to Portsmouth, and run every hour and irregularly throughout the night.
East Cowes is very close to Newport, with ferries going to Southampton.
Yarmouth is the port of West Wight, and ferries go to Lymington, in the New Forest.
It should be easy getting rides into the island from any of the car ferry ports at Southampton, Portsmouth or Lymington. Drivers pay for their vehicles and not per passenger on both WightLink and Red Funnel ferries. Simon easily got a lift on the Red Funnel ferry from Southampton in August 2017, after waiting less than 10 minutes outside the port with a sign for "Isle of Wight". Generally people sympathise a lot with people wanting to travel for free on the island, because public transport (ferries and buses) are very expensive.
Accommodation, Sleep, Eat
The Isle of Wight is extremely rambler-friendly, and so wild camping could be deemed quite acceptable across most of the island. A lot of the beaches become quiet by nighttime, though care should be taken for the incoming tides (particularly relevant if camping on the west coast, where the high tide can come up to the cliffs). There are also many smaller stretches of woodlands all around the island, and much downland especially from Freshwater all the way down the west coast and around to Shanklin.
There are plenty of abandoned buildings too, if shelter is needed.
There are also A LOT of people living in vans on the island, who may be happy for you to pitch with them (they can normally be found in evening at scenic spots).
For eating, Simon has yet to have had much luck with skipping on the island [as of March 2017]. He set up an Isle of Wight Freegans Facebook group, which is worth checking for updates on the skipping situation.