A trip from Tokyo to Naoshima in search of Japan's most striking artworks

At the height of his late-20th-century British Saturday-night TV fame, the late Australian TV critic and travel broadcaster Clive James would show clips of Endurance, the most extreme game show Japanese television had to offer, in which people would eat insects as they tumbled from huge inflatable ladders into empty swimming pools full of mouse traps. No wonder a generation grew up believing Japan to be some sort of giant self-harm version of It’s A Knockout.

Fortunately, five years ago, an alluring shot of Mount Fuji on Instagram drew me back to Japan, after a 25-year break, where I discovered a world beyond sado-masochistic game shows; one of forests, rivers, landscapes, seascapes, sculpture parks, architecture, food, fashions and shops that were so magnetic I’ve been back four times since.

If arriving into Tokyo for the first time, a degree of international familiarity, as well as uninterrupted views of Mount Fuji, can be found at the Mandarin Oriental in the business district of Nihonbashi, the very centre of the original Tokyo. Look down from your room and you will see Shinkansen (bullet trains) sliding gracefully into Tokyo Station.

A few blocks away is the Tokyo Imperial Palace, the main residence of the Japanese Emperor and a must for fans of enormous moats, stone walls and history. There are, of course, countless restaurants, people and adventures to experience and enjoy in Tokyo, but the bookshop chain Tsutaya at Daikanyama is on another level to any other bookshop anywhere, the Kapital clothing shops stretch your imagination like few Western shops will, and Daiwa Sushi in the docks is a must-visit.

Board a Shinkansen and 90 minutes away from the metropolis, in Hakone, the Japanese Lake District, you will find a tree-lined valley overlooking a powerful river and numerous hot-spring onsen hotels. Choose the KAI Hakone and, as you sit with your feet in the river, gazing up at the dense forest as the water crashes from boulder to boulder, you’ll soon forget the city of 37 million people you’ve just left behind. No wonder Tokyoites are apt to pop down for a day’s rest and relaxation.

Unexpectedly, at 808 Monsmare, Hakone, you will find some of the world’s best pizzas outside of Naples. And at the truly astounding Hakone Open-Air Museum, you’ll discover sculptures like the brilliantly playful kids-only hand-knitted playscape by Toshiko Horiuchi MacAdam, and a Picasso ceramics gallery.

Next stop: the Shinkansen propels you towards Naoshima. You may have seen images of Yayoi Kusama’s giant pumpkins on Japan’s famous ‘art island’. However, her presence starts on the white car ferries that take you on the 20-minute ride across the Seto Inland Sea, each emblazoned with huge scarlet chevrons or circles – as if the Pet Shop Boys have redesigned a Red Cross boat.

For high-end accommodation, check in to the hotel at Benesse House Museum – in its grounds sits Kusama’s much Instagrammed yellow pumpkin. Here you’ll find Yukinori Yanagi’s sizeable wall of international flags made of sand, which holds your attention for quite some time before you realise that the whole installation is connected by Plexiglas tubes and is home to an ant colony. The slight degradation of each flag is a result of the insects’ busy travels.

Elsewhere, Yayoi Kusama’s Narcissus Garden features 1,700 stainless-steel spheres spread out across the paths, pond and layers of a garden and into the corridors of a concrete structure. Hiroshi Sugimoto’s stunning collection of sea photographs is presented on either side of a view of the Seto Inland Sea itself.

There’s no end to the quality and impact of the artworks here, best enjoyed by hiring electric bikes, which allow you to explore an art trail of truly diverse works housed in the alleyways between homes with Shou Suggi Ban charred-pine exteriors. Here you’ll frequently run into utterly unexpected installations: a room of total darkness; a former dentist’s house where extracted teeth are embedded in the walls; a huge Statue of Liberty climbing two storeys of a house filled with nautical ephemera.

Despite the island’s thriving community of creatives, perhaps the greatest beauty you experience here is not manmade; it’s the view at the end of the day as the ferry takes you back to the mainland. Later, when you look back at your pictures and you see the splendour of the seascape, you’ll wonder, ‘How on earth did I get used to this?’