Nikko
Nikko sits in the forested mountains of Tochigi Prefecture, two hours north of Tokyo by train, and contains some of the most ornate religious architecture in Japan. The Toshogu Shrine complex — built in the 17th century as a mausoleum for Tokugawa Ieyasu, the shogun who unified Japan — is a riot of gilded carvings, lacquered gates, and painted panels set beneath towering cedar trees that have stood for four centuries. Beyond the shrine complex, Nikko National Park offers waterfalls, mountain lakes, hot springs, and a stretch of the old Edo-period highway lined with ancient cryptomeria cedars that is one of the most atmospheric walks in Japan.
Matsumoto
Matsumoto is a beautifully preserved castle town in the Japan Alps, two and a half hours west of Tokyo on the Azusa Limited Express from Shinjuku. Its centrepiece is Matsumoto Castle — nicknamed the Crow Castle for its dramatic black exterior — one of only twelve original castles remaining in Japan and a National Treasure. The castle sits at the edge of the old town, reflected in the moat, with the snow-capped Japanese Alps rising behind it. The surrounding streets of the Nakamachi and Nawate districts are lined with Edo-period kura storehouses, sake breweries, and craft shops that give Matsumoto a character unlike anywhere closer to Tokyo.
Izu Peninsula
The Izu Peninsula juts into the Pacific south of Tokyo and is one of the most scenically varied day trip destinations in the region — a landscape of dramatic sea cliffs, hidden coves, bamboo forests, geothermal hot springs, and quiet fishing villages strung along a coastline that faces both the open Pacific and the calmer waters of Suruga Bay, with Mount Fuji visible from the west coast on clear days. The peninsula has been a retreat for artists, writers, and the Tokyo wealthy since the Meiji era, and its towns — Atami, Ito, Shuzenji, Shimoda — each have a distinct character ranging from the onsen resort bustle of Atami to the quiet beauty of Shuzenji's temple valley.
Nagano & Snow Monkeys
Nagano Prefecture is one of Japan's most dramatic mountain landscapes — a landlocked region of soaring peaks, deep river valleys, and ancient temple towns that hosted the 1998 Winter Olympics and remains one of the country's premier destinations for winter travel. The star attraction is Jigokudani Monkey Park, set in a steep snow-covered valley north of Nagano city, where a troop of wild Japanese macaques descends from the forest each winter morning to soak in a natural hot spring pool — one of the most extraordinary wildlife spectacles in Japan and unlike anything else in East Asia. The nearby town of Yudanaka is a classic hot spring resort, and Zenko-ji Temple in Nagano city, one of Japan's most important Buddhist pilgrimage sites, is a magnificent stop in its own right.
Kyoto
Kyoto was Japan's imperial capital for over a thousand years and remains the country's most concentrated repository of traditional culture — a city of 1,600 Buddhist temples, 400 Shinto shrines, 17 UNESCO World Heritage Sites, geisha districts, imperial palaces, zen rock gardens, and some of the finest kaiseki cuisine in the world. With two and a quarter hours by Shinkansen from Tokyo, it is the most rewarding single long day trip or overnight destination from the capital. The city is large but its historic areas — Higashiyama, Arashiyama, Fushimi, Nishiki — are distinct enough that a well-planned itinerary with Terry can take in three or four of them in a single focused day.
Osaka
Osaka is Japan's most extroverted city — louder, friendlier, and hungrier than Tokyo, with a food culture so celebrated that the phrase kuidaore ("eat until you drop") is the city's unofficial motto. The historic castle, the neon-lit Dotonbori canal district, the covered shopping streets of Shinsaibashi, and the underground food universe of Kuromon Market together make Osaka one of the most immediately enjoyable cities in Japan. It pairs naturally with Kyoto, just 15 minutes away by Shinkansen, making a combined overnight trip that covers Japan's two great contrasting urban personalities — refined imperial culture and joyful street-level energy — in a single journey.
Nara
Nara was Japan's first permanent capital (710–784 AD) and contains a remarkable concentration of ancient Buddhist temples, Shinto shrines, and artifacts from Japan's earliest recorded history — including Todaiji, the world's largest wooden structure, which houses a 15-metre bronze Buddha cast in the 8th century. The central Nara Park, a vast green space connecting the major historic sites, is home to over 1,000 freely roaming sika deer that have been considered sacred messengers of the gods since the city's founding and show a disconcerting willingness to bow in exchange for the deer crackers sold throughout the park. Nara combines best with Kyoto or Osaka as part of an overnight trip to the Kansai region.